Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides
A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, ga...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Kollatos, Nikolaos [verfasserIn] |
|---|
| Format: |
Artikel |
|---|---|
| Sprache: |
Englisch |
| Erschienen: |
2015 |
|---|
| Rechteinformationen: |
Nutzungsrecht: Copyright © 2015 Elsevier Ltd. All rights reserved. |
|---|
| Übergeordnetes Werk: |
Enthalten in: Carbohydrate research - Amsterdam : Elsevier, 1965, 407(2015), Seite 170-178 |
|---|---|
| Übergeordnetes Werk: |
volume:407 ; year:2015 ; pages:170-178 |
| Links: |
|---|
| DOI / URN: |
10.1016/j.carres.2015.01.021 |
|---|
| Katalog-ID: |
OLC1964133815 |
|---|
| LEADER | 01000caa a2200265 4500 | ||
|---|---|---|---|
| 001 | OLC1964133815 | ||
| 003 | DE-627 | ||
| 005 | 20230508073608.0 | ||
| 007 | tu | ||
| 008 | 160206s2015 xx ||||| 00| ||eng c | ||
| 024 | 7 | |a 10.1016/j.carres.2015.01.021 |2 doi | |
| 028 | 5 | 2 | |a PQ20160617 |
| 035 | |a (DE-627)OLC1964133815 | ||
| 035 | |a (DE-599)GBVOLC1964133815 | ||
| 035 | |a (PRQ)c1284-35294f655dcc781713bac182a3ce769fe102a5a8d61358ad1719f4ea094ded540 | ||
| 035 | |a (KEY)0026786420150000407000000170branchedchainsugarnucleosidesstereocontrolledsynth | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 082 | 0 | 4 | |a 660 |q DE-600 |
| 100 | 1 | |a Kollatos, Nikolaos |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides |
| 264 | 1 | |c 2015 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ohne Hilfsmittel zu benutzen |b n |2 rdamedia | ||
| 338 | |a Band |b nc |2 rdacarrier | ||
| 520 | |a A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-α-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-β-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3'-deoxy-3'-C-trifluoromethyl and 3'-deoxy-3'-C-methyl-β-d-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3'-deoxy-3'-C-methyl- ribonucleoside 11b showed significant cytotoxic activity (∼7 μM) almost equally active against a variety of tumor cell lines. | ||
| 540 | |a Nutzungsrecht: Copyright © 2015 Elsevier Ltd. All rights reserved. | ||
| 650 | 4 | |a Nucleosides - pharmacology | |
| 650 | 4 | |a Oligosaccharides, Branched-Chain - chemistry | |
| 650 | 4 | |a Nucleosides - chemical synthesis | |
| 650 | 4 | |a Oligosaccharides, Branched-Chain - chemical synthesis | |
| 650 | 4 | |a Cytostatic Agents - chemical synthesis | |
| 650 | 4 | |a Antiviral Agents - pharmacology | |
| 650 | 4 | |a Antiviral Agents - chemical synthesis | |
| 650 | 4 | |a Nucleosides - chemistry | |
| 650 | 4 | |a Cytostatic Agents - chemistry | |
| 650 | 4 | |a Cell Proliferation - drug effects | |
| 650 | 4 | |a Cytostatic Agents - pharmacology | |
| 650 | 4 | |a Antiviral Agents - chemistry | |
| 650 | 4 | |a Oligosaccharides, Branched-Chain - pharmacology | |
| 700 | 1 | |a Manta, Stella |4 oth | |
| 700 | 1 | |a Dimopoulou, Athina |4 oth | |
| 700 | 1 | |a Parmenopoulou, Vanessa |4 oth | |
| 700 | 1 | |a Triantakonstanti, Virginia V |4 oth | |
| 700 | 1 | |a Kellici, Tahsin |4 oth | |
| 700 | 1 | |a Mavromoustakos, Thomas |4 oth | |
| 700 | 1 | |a Schols, Dominique |4 oth | |
| 700 | 1 | |a Komiotis, Dimitri |4 oth | |
| 773 | 0 | 8 | |i Enthalten in |t Carbohydrate research |d Amsterdam : Elsevier, 1965 |g 407(2015), Seite 170-178 |w (DE-627)129067776 |w (DE-600)1435-7 |w (DE-576)014399229 |x 0008-6215 |7 nnns |
| 773 | 1 | 8 | |g volume:407 |g year:2015 |g pages:170-178 |
| 856 | 4 | 1 | |u http://dx.doi.org/10.1016/j.carres.2015.01.021 |3 Volltext |
| 856 | 4 | 2 | |u http://www.ncbi.nlm.nih.gov/pubmed/25812993 |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a SYSFLAG_A | ||
| 912 | |a GBV_OLC | ||
| 912 | |a SSG-OLC-TEC | ||
| 912 | |a SSG-OLC-CHE | ||
| 912 | |a SSG-OLC-PHA | ||
| 912 | |a SSG-OLC-DE-84 | ||
| 912 | |a GBV_ILN_70 | ||
| 912 | |a GBV_ILN_4012 | ||
| 912 | |a GBV_ILN_4305 | ||
| 951 | |a AR | ||
| 952 | |d 407 |j 2015 |h 170-178 | ||
| author_variant |
n k nk |
|---|---|
| matchkey_str |
article:00086215:2015----::rnhdhisgruloieseecnrlesnhssnbovlainfoe3tilooe |
| hierarchy_sort_str |
2015 |
| publishDate |
2015 |
| allfields |
10.1016/j.carres.2015.01.021 doi PQ20160617 (DE-627)OLC1964133815 (DE-599)GBVOLC1964133815 (PRQ)c1284-35294f655dcc781713bac182a3ce769fe102a5a8d61358ad1719f4ea094ded540 (KEY)0026786420150000407000000170branchedchainsugarnucleosidesstereocontrolledsynth DE-627 ger DE-627 rakwb eng 660 DE-600 Kollatos, Nikolaos verfasserin aut Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-α-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-β-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3'-deoxy-3'-C-trifluoromethyl and 3'-deoxy-3'-C-methyl-β-d-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3'-deoxy-3'-C-methyl- ribonucleoside 11b showed significant cytotoxic activity (∼7 μM) almost equally active against a variety of tumor cell lines. Nutzungsrecht: Copyright © 2015 Elsevier Ltd. All rights reserved. Nucleosides - pharmacology Oligosaccharides, Branched-Chain - chemistry Nucleosides - chemical synthesis Oligosaccharides, Branched-Chain - chemical synthesis Cytostatic Agents - chemical synthesis Antiviral Agents - pharmacology Antiviral Agents - chemical synthesis Nucleosides - chemistry Cytostatic Agents - chemistry Cell Proliferation - drug effects Cytostatic Agents - pharmacology Antiviral Agents - chemistry Oligosaccharides, Branched-Chain - pharmacology Manta, Stella oth Dimopoulou, Athina oth Parmenopoulou, Vanessa oth Triantakonstanti, Virginia V oth Kellici, Tahsin oth Mavromoustakos, Thomas oth Schols, Dominique oth Komiotis, Dimitri oth Enthalten in Carbohydrate research Amsterdam : Elsevier, 1965 407(2015), Seite 170-178 (DE-627)129067776 (DE-600)1435-7 (DE-576)014399229 0008-6215 nnns volume:407 year:2015 pages:170-178 http://dx.doi.org/10.1016/j.carres.2015.01.021 Volltext http://www.ncbi.nlm.nih.gov/pubmed/25812993 GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_4012 GBV_ILN_4305 AR 407 2015 170-178 |
| spelling |
10.1016/j.carres.2015.01.021 doi PQ20160617 (DE-627)OLC1964133815 (DE-599)GBVOLC1964133815 (PRQ)c1284-35294f655dcc781713bac182a3ce769fe102a5a8d61358ad1719f4ea094ded540 (KEY)0026786420150000407000000170branchedchainsugarnucleosidesstereocontrolledsynth DE-627 ger DE-627 rakwb eng 660 DE-600 Kollatos, Nikolaos verfasserin aut Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-α-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-β-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3'-deoxy-3'-C-trifluoromethyl and 3'-deoxy-3'-C-methyl-β-d-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3'-deoxy-3'-C-methyl- ribonucleoside 11b showed significant cytotoxic activity (∼7 μM) almost equally active against a variety of tumor cell lines. Nutzungsrecht: Copyright © 2015 Elsevier Ltd. All rights reserved. Nucleosides - pharmacology Oligosaccharides, Branched-Chain - chemistry Nucleosides - chemical synthesis Oligosaccharides, Branched-Chain - chemical synthesis Cytostatic Agents - chemical synthesis Antiviral Agents - pharmacology Antiviral Agents - chemical synthesis Nucleosides - chemistry Cytostatic Agents - chemistry Cell Proliferation - drug effects Cytostatic Agents - pharmacology Antiviral Agents - chemistry Oligosaccharides, Branched-Chain - pharmacology Manta, Stella oth Dimopoulou, Athina oth Parmenopoulou, Vanessa oth Triantakonstanti, Virginia V oth Kellici, Tahsin oth Mavromoustakos, Thomas oth Schols, Dominique oth Komiotis, Dimitri oth Enthalten in Carbohydrate research Amsterdam : Elsevier, 1965 407(2015), Seite 170-178 (DE-627)129067776 (DE-600)1435-7 (DE-576)014399229 0008-6215 nnns volume:407 year:2015 pages:170-178 http://dx.doi.org/10.1016/j.carres.2015.01.021 Volltext http://www.ncbi.nlm.nih.gov/pubmed/25812993 GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_4012 GBV_ILN_4305 AR 407 2015 170-178 |
| allfields_unstemmed |
10.1016/j.carres.2015.01.021 doi PQ20160617 (DE-627)OLC1964133815 (DE-599)GBVOLC1964133815 (PRQ)c1284-35294f655dcc781713bac182a3ce769fe102a5a8d61358ad1719f4ea094ded540 (KEY)0026786420150000407000000170branchedchainsugarnucleosidesstereocontrolledsynth DE-627 ger DE-627 rakwb eng 660 DE-600 Kollatos, Nikolaos verfasserin aut Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-α-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-β-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3'-deoxy-3'-C-trifluoromethyl and 3'-deoxy-3'-C-methyl-β-d-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3'-deoxy-3'-C-methyl- ribonucleoside 11b showed significant cytotoxic activity (∼7 μM) almost equally active against a variety of tumor cell lines. Nutzungsrecht: Copyright © 2015 Elsevier Ltd. All rights reserved. Nucleosides - pharmacology Oligosaccharides, Branched-Chain - chemistry Nucleosides - chemical synthesis Oligosaccharides, Branched-Chain - chemical synthesis Cytostatic Agents - chemical synthesis Antiviral Agents - pharmacology Antiviral Agents - chemical synthesis Nucleosides - chemistry Cytostatic Agents - chemistry Cell Proliferation - drug effects Cytostatic Agents - pharmacology Antiviral Agents - chemistry Oligosaccharides, Branched-Chain - pharmacology Manta, Stella oth Dimopoulou, Athina oth Parmenopoulou, Vanessa oth Triantakonstanti, Virginia V oth Kellici, Tahsin oth Mavromoustakos, Thomas oth Schols, Dominique oth Komiotis, Dimitri oth Enthalten in Carbohydrate research Amsterdam : Elsevier, 1965 407(2015), Seite 170-178 (DE-627)129067776 (DE-600)1435-7 (DE-576)014399229 0008-6215 nnns volume:407 year:2015 pages:170-178 http://dx.doi.org/10.1016/j.carres.2015.01.021 Volltext http://www.ncbi.nlm.nih.gov/pubmed/25812993 GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_4012 GBV_ILN_4305 AR 407 2015 170-178 |
| allfieldsGer |
10.1016/j.carres.2015.01.021 doi PQ20160617 (DE-627)OLC1964133815 (DE-599)GBVOLC1964133815 (PRQ)c1284-35294f655dcc781713bac182a3ce769fe102a5a8d61358ad1719f4ea094ded540 (KEY)0026786420150000407000000170branchedchainsugarnucleosidesstereocontrolledsynth DE-627 ger DE-627 rakwb eng 660 DE-600 Kollatos, Nikolaos verfasserin aut Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-α-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-β-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3'-deoxy-3'-C-trifluoromethyl and 3'-deoxy-3'-C-methyl-β-d-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3'-deoxy-3'-C-methyl- ribonucleoside 11b showed significant cytotoxic activity (∼7 μM) almost equally active against a variety of tumor cell lines. Nutzungsrecht: Copyright © 2015 Elsevier Ltd. All rights reserved. Nucleosides - pharmacology Oligosaccharides, Branched-Chain - chemistry Nucleosides - chemical synthesis Oligosaccharides, Branched-Chain - chemical synthesis Cytostatic Agents - chemical synthesis Antiviral Agents - pharmacology Antiviral Agents - chemical synthesis Nucleosides - chemistry Cytostatic Agents - chemistry Cell Proliferation - drug effects Cytostatic Agents - pharmacology Antiviral Agents - chemistry Oligosaccharides, Branched-Chain - pharmacology Manta, Stella oth Dimopoulou, Athina oth Parmenopoulou, Vanessa oth Triantakonstanti, Virginia V oth Kellici, Tahsin oth Mavromoustakos, Thomas oth Schols, Dominique oth Komiotis, Dimitri oth Enthalten in Carbohydrate research Amsterdam : Elsevier, 1965 407(2015), Seite 170-178 (DE-627)129067776 (DE-600)1435-7 (DE-576)014399229 0008-6215 nnns volume:407 year:2015 pages:170-178 http://dx.doi.org/10.1016/j.carres.2015.01.021 Volltext http://www.ncbi.nlm.nih.gov/pubmed/25812993 GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_4012 GBV_ILN_4305 AR 407 2015 170-178 |
| allfieldsSound |
10.1016/j.carres.2015.01.021 doi PQ20160617 (DE-627)OLC1964133815 (DE-599)GBVOLC1964133815 (PRQ)c1284-35294f655dcc781713bac182a3ce769fe102a5a8d61358ad1719f4ea094ded540 (KEY)0026786420150000407000000170branchedchainsugarnucleosidesstereocontrolledsynth DE-627 ger DE-627 rakwb eng 660 DE-600 Kollatos, Nikolaos verfasserin aut Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-α-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-β-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3'-deoxy-3'-C-trifluoromethyl and 3'-deoxy-3'-C-methyl-β-d-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3'-deoxy-3'-C-methyl- ribonucleoside 11b showed significant cytotoxic activity (∼7 μM) almost equally active against a variety of tumor cell lines. Nutzungsrecht: Copyright © 2015 Elsevier Ltd. All rights reserved. Nucleosides - pharmacology Oligosaccharides, Branched-Chain - chemistry Nucleosides - chemical synthesis Oligosaccharides, Branched-Chain - chemical synthesis Cytostatic Agents - chemical synthesis Antiviral Agents - pharmacology Antiviral Agents - chemical synthesis Nucleosides - chemistry Cytostatic Agents - chemistry Cell Proliferation - drug effects Cytostatic Agents - pharmacology Antiviral Agents - chemistry Oligosaccharides, Branched-Chain - pharmacology Manta, Stella oth Dimopoulou, Athina oth Parmenopoulou, Vanessa oth Triantakonstanti, Virginia V oth Kellici, Tahsin oth Mavromoustakos, Thomas oth Schols, Dominique oth Komiotis, Dimitri oth Enthalten in Carbohydrate research Amsterdam : Elsevier, 1965 407(2015), Seite 170-178 (DE-627)129067776 (DE-600)1435-7 (DE-576)014399229 0008-6215 nnns volume:407 year:2015 pages:170-178 http://dx.doi.org/10.1016/j.carres.2015.01.021 Volltext http://www.ncbi.nlm.nih.gov/pubmed/25812993 GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_4012 GBV_ILN_4305 AR 407 2015 170-178 |
| language |
English |
| source |
Enthalten in Carbohydrate research 407(2015), Seite 170-178 volume:407 year:2015 pages:170-178 |
| sourceStr |
Enthalten in Carbohydrate research 407(2015), Seite 170-178 volume:407 year:2015 pages:170-178 |
| format_phy_str_mv |
Article |
| institution |
findex.gbv.de |
| topic_facet |
Nucleosides - pharmacology Oligosaccharides, Branched-Chain - chemistry Nucleosides - chemical synthesis Oligosaccharides, Branched-Chain - chemical synthesis Cytostatic Agents - chemical synthesis Antiviral Agents - pharmacology Antiviral Agents - chemical synthesis Nucleosides - chemistry Cytostatic Agents - chemistry Cell Proliferation - drug effects Cytostatic Agents - pharmacology Antiviral Agents - chemistry Oligosaccharides, Branched-Chain - pharmacology |
| dewey-raw |
660 |
| isfreeaccess_bool |
false |
| container_title |
Carbohydrate research |
| authorswithroles_txt_mv |
Kollatos, Nikolaos @@aut@@ Manta, Stella @@oth@@ Dimopoulou, Athina @@oth@@ Parmenopoulou, Vanessa @@oth@@ Triantakonstanti, Virginia V @@oth@@ Kellici, Tahsin @@oth@@ Mavromoustakos, Thomas @@oth@@ Schols, Dominique @@oth@@ Komiotis, Dimitri @@oth@@ |
| publishDateDaySort_date |
2015-01-01T00:00:00Z |
| hierarchy_top_id |
129067776 |
| dewey-sort |
3660 |
| id |
OLC1964133815 |
| language_de |
englisch |
| fullrecord |
<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a2200265 4500</leader><controlfield tag="001">OLC1964133815</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20230508073608.0</controlfield><controlfield tag="007">tu</controlfield><controlfield tag="008">160206s2015 xx ||||| 00| ||eng c</controlfield><datafield tag="024" ind1="7" ind2=" "><subfield code="a">10.1016/j.carres.2015.01.021</subfield><subfield code="2">doi</subfield></datafield><datafield tag="028" ind1="5" ind2="2"><subfield code="a">PQ20160617</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)OLC1964133815</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)GBVOLC1964133815</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(PRQ)c1284-35294f655dcc781713bac182a3ce769fe102a5a8d61358ad1719f4ea094ded540</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(KEY)0026786420150000407000000170branchedchainsugarnucleosidesstereocontrolledsynth</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="082" ind1="0" ind2="4"><subfield code="a">660</subfield><subfield code="q">DE-600</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Kollatos, Nikolaos</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">2015</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">Text</subfield><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">ohne Hilfsmittel zu benutzen</subfield><subfield code="b">n</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">Band</subfield><subfield code="b">nc</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-α-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-β-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3'-deoxy-3'-C-trifluoromethyl and 3'-deoxy-3'-C-methyl-β-d-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3'-deoxy-3'-C-methyl- ribonucleoside 11b showed significant cytotoxic activity (∼7 μM) almost equally active against a variety of tumor cell lines.</subfield></datafield><datafield tag="540" ind1=" " ind2=" "><subfield code="a">Nutzungsrecht: Copyright © 2015 Elsevier Ltd. All rights reserved.</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Nucleosides - pharmacology</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Oligosaccharides, Branched-Chain - chemistry</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Nucleosides - chemical synthesis</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Oligosaccharides, Branched-Chain - chemical synthesis</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Cytostatic Agents - chemical synthesis</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Antiviral Agents - pharmacology</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Antiviral Agents - chemical synthesis</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Nucleosides - chemistry</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Cytostatic Agents - chemistry</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Cell Proliferation - drug effects</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Cytostatic Agents - pharmacology</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Antiviral Agents - chemistry</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Oligosaccharides, Branched-Chain - pharmacology</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Manta, Stella</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Dimopoulou, Athina</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Parmenopoulou, Vanessa</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Triantakonstanti, Virginia V</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Kellici, Tahsin</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Mavromoustakos, Thomas</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Schols, Dominique</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Komiotis, Dimitri</subfield><subfield code="4">oth</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">Enthalten in</subfield><subfield code="t">Carbohydrate research</subfield><subfield code="d">Amsterdam : Elsevier, 1965</subfield><subfield code="g">407(2015), Seite 170-178</subfield><subfield code="w">(DE-627)129067776</subfield><subfield code="w">(DE-600)1435-7</subfield><subfield code="w">(DE-576)014399229</subfield><subfield code="x">0008-6215</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:407</subfield><subfield code="g">year:2015</subfield><subfield code="g">pages:170-178</subfield></datafield><datafield tag="856" ind1="4" ind2="1"><subfield code="u">http://dx.doi.org/10.1016/j.carres.2015.01.021</subfield><subfield code="3">Volltext</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="u">http://www.ncbi.nlm.nih.gov/pubmed/25812993</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_OLC</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-TEC</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-CHE</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-PHA</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-DE-84</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_70</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4012</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4305</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">407</subfield><subfield code="j">2015</subfield><subfield code="h">170-178</subfield></datafield></record></collection>
|
| author |
Kollatos, Nikolaos |
| spellingShingle |
Kollatos, Nikolaos ddc 660 misc Nucleosides - pharmacology misc Oligosaccharides, Branched-Chain - chemistry misc Nucleosides - chemical synthesis misc Oligosaccharides, Branched-Chain - chemical synthesis misc Cytostatic Agents - chemical synthesis misc Antiviral Agents - pharmacology misc Antiviral Agents - chemical synthesis misc Nucleosides - chemistry misc Cytostatic Agents - chemistry misc Cell Proliferation - drug effects misc Cytostatic Agents - pharmacology misc Antiviral Agents - chemistry misc Oligosaccharides, Branched-Chain - pharmacology Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides |
| authorStr |
Kollatos, Nikolaos |
| ppnlink_with_tag_str_mv |
@@773@@(DE-627)129067776 |
| format |
Article |
| dewey-ones |
660 - Chemical engineering |
| delete_txt_mv |
keep |
| author_role |
aut |
| collection |
OLC |
| remote_str |
false |
| illustrated |
Not Illustrated |
| issn |
0008-6215 |
| topic_title |
660 DE-600 Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides Nucleosides - pharmacology Oligosaccharides, Branched-Chain - chemistry Nucleosides - chemical synthesis Oligosaccharides, Branched-Chain - chemical synthesis Cytostatic Agents - chemical synthesis Antiviral Agents - pharmacology Antiviral Agents - chemical synthesis Nucleosides - chemistry Cytostatic Agents - chemistry Cell Proliferation - drug effects Cytostatic Agents - pharmacology Antiviral Agents - chemistry Oligosaccharides, Branched-Chain - pharmacology |
| topic |
ddc 660 misc Nucleosides - pharmacology misc Oligosaccharides, Branched-Chain - chemistry misc Nucleosides - chemical synthesis misc Oligosaccharides, Branched-Chain - chemical synthesis misc Cytostatic Agents - chemical synthesis misc Antiviral Agents - pharmacology misc Antiviral Agents - chemical synthesis misc Nucleosides - chemistry misc Cytostatic Agents - chemistry misc Cell Proliferation - drug effects misc Cytostatic Agents - pharmacology misc Antiviral Agents - chemistry misc Oligosaccharides, Branched-Chain - pharmacology |
| topic_unstemmed |
ddc 660 misc Nucleosides - pharmacology misc Oligosaccharides, Branched-Chain - chemistry misc Nucleosides - chemical synthesis misc Oligosaccharides, Branched-Chain - chemical synthesis misc Cytostatic Agents - chemical synthesis misc Antiviral Agents - pharmacology misc Antiviral Agents - chemical synthesis misc Nucleosides - chemistry misc Cytostatic Agents - chemistry misc Cell Proliferation - drug effects misc Cytostatic Agents - pharmacology misc Antiviral Agents - chemistry misc Oligosaccharides, Branched-Chain - pharmacology |
| topic_browse |
ddc 660 misc Nucleosides - pharmacology misc Oligosaccharides, Branched-Chain - chemistry misc Nucleosides - chemical synthesis misc Oligosaccharides, Branched-Chain - chemical synthesis misc Cytostatic Agents - chemical synthesis misc Antiviral Agents - pharmacology misc Antiviral Agents - chemical synthesis misc Nucleosides - chemistry misc Cytostatic Agents - chemistry misc Cell Proliferation - drug effects misc Cytostatic Agents - pharmacology misc Antiviral Agents - chemistry misc Oligosaccharides, Branched-Chain - pharmacology |
| format_facet |
Aufsätze Gedruckte Aufsätze |
| format_main_str_mv |
Text Zeitschrift/Artikel |
| carriertype_str_mv |
nc |
| author2_variant |
s m sm a d ad v p vp v v t vv vvt t k tk t m tm d s ds d k dk |
| hierarchy_parent_title |
Carbohydrate research |
| hierarchy_parent_id |
129067776 |
| dewey-tens |
660 - Chemical engineering |
| hierarchy_top_title |
Carbohydrate research |
| isfreeaccess_txt |
false |
| familylinks_str_mv |
(DE-627)129067776 (DE-600)1435-7 (DE-576)014399229 |
| title |
Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides |
| ctrlnum |
(DE-627)OLC1964133815 (DE-599)GBVOLC1964133815 (PRQ)c1284-35294f655dcc781713bac182a3ce769fe102a5a8d61358ad1719f4ea094ded540 (KEY)0026786420150000407000000170branchedchainsugarnucleosidesstereocontrolledsynth |
| title_full |
Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides |
| author_sort |
Kollatos, Nikolaos |
| journal |
Carbohydrate research |
| journalStr |
Carbohydrate research |
| lang_code |
eng |
| isOA_bool |
false |
| dewey-hundreds |
600 - Technology |
| recordtype |
marc |
| publishDateSort |
2015 |
| contenttype_str_mv |
txt |
| container_start_page |
170 |
| author_browse |
Kollatos, Nikolaos |
| container_volume |
407 |
| class |
660 DE-600 |
| format_se |
Aufsätze |
| author-letter |
Kollatos, Nikolaos |
| doi_str_mv |
10.1016/j.carres.2015.01.021 |
| dewey-full |
660 |
| title_sort |
branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-c-trifluoromethyl and 3'-c-methyl pyranonucleosides |
| title_auth |
Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides |
| abstract |
A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-α-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-β-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3'-deoxy-3'-C-trifluoromethyl and 3'-deoxy-3'-C-methyl-β-d-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3'-deoxy-3'-C-methyl- ribonucleoside 11b showed significant cytotoxic activity (∼7 μM) almost equally active against a variety of tumor cell lines. |
| abstractGer |
A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-α-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-β-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3'-deoxy-3'-C-trifluoromethyl and 3'-deoxy-3'-C-methyl-β-d-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3'-deoxy-3'-C-methyl- ribonucleoside 11b showed significant cytotoxic activity (∼7 μM) almost equally active against a variety of tumor cell lines. |
| abstract_unstemmed |
A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-α-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-β-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3'-deoxy-3'-C-trifluoromethyl and 3'-deoxy-3'-C-methyl-β-d-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3'-deoxy-3'-C-methyl- ribonucleoside 11b showed significant cytotoxic activity (∼7 μM) almost equally active against a variety of tumor cell lines. |
| collection_details |
GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_4012 GBV_ILN_4305 |
| title_short |
Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides |
| url |
http://dx.doi.org/10.1016/j.carres.2015.01.021 http://www.ncbi.nlm.nih.gov/pubmed/25812993 |
| remote_bool |
false |
| author2 |
Manta, Stella Dimopoulou, Athina Parmenopoulou, Vanessa Triantakonstanti, Virginia V Kellici, Tahsin Mavromoustakos, Thomas Schols, Dominique Komiotis, Dimitri |
| author2Str |
Manta, Stella Dimopoulou, Athina Parmenopoulou, Vanessa Triantakonstanti, Virginia V Kellici, Tahsin Mavromoustakos, Thomas Schols, Dominique Komiotis, Dimitri |
| ppnlink |
129067776 |
| mediatype_str_mv |
n |
| isOA_txt |
false |
| hochschulschrift_bool |
false |
| author2_role |
oth oth oth oth oth oth oth oth |
| doi_str |
10.1016/j.carres.2015.01.021 |
| up_date |
2024-07-04T07:15:30.870Z |
| _version_ |
1803631807295389696 |
| fullrecord_marcxml |
<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a2200265 4500</leader><controlfield tag="001">OLC1964133815</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20230508073608.0</controlfield><controlfield tag="007">tu</controlfield><controlfield tag="008">160206s2015 xx ||||| 00| ||eng c</controlfield><datafield tag="024" ind1="7" ind2=" "><subfield code="a">10.1016/j.carres.2015.01.021</subfield><subfield code="2">doi</subfield></datafield><datafield tag="028" ind1="5" ind2="2"><subfield code="a">PQ20160617</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)OLC1964133815</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)GBVOLC1964133815</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(PRQ)c1284-35294f655dcc781713bac182a3ce769fe102a5a8d61358ad1719f4ea094ded540</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(KEY)0026786420150000407000000170branchedchainsugarnucleosidesstereocontrolledsynth</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="082" ind1="0" ind2="4"><subfield code="a">660</subfield><subfield code="q">DE-600</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Kollatos, Nikolaos</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3'-C-trifluoromethyl and 3'-C-methyl pyranonucleosides</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">2015</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">Text</subfield><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">ohne Hilfsmittel zu benutzen</subfield><subfield code="b">n</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">Band</subfield><subfield code="b">nc</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">A new series of 3'-C-trifluoromethyl- and 3'-C-methyl-β-d-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-α-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-β-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3'-deoxy-3'-C-trifluoromethyl and 3'-deoxy-3'-C-methyl-β-d-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3'-deoxy-3'-C-methyl- ribonucleoside 11b showed significant cytotoxic activity (∼7 μM) almost equally active against a variety of tumor cell lines.</subfield></datafield><datafield tag="540" ind1=" " ind2=" "><subfield code="a">Nutzungsrecht: Copyright © 2015 Elsevier Ltd. All rights reserved.</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Nucleosides - pharmacology</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Oligosaccharides, Branched-Chain - chemistry</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Nucleosides - chemical synthesis</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Oligosaccharides, Branched-Chain - chemical synthesis</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Cytostatic Agents - chemical synthesis</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Antiviral Agents - pharmacology</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Antiviral Agents - chemical synthesis</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Nucleosides - chemistry</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Cytostatic Agents - chemistry</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Cell Proliferation - drug effects</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Cytostatic Agents - pharmacology</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Antiviral Agents - chemistry</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Oligosaccharides, Branched-Chain - pharmacology</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Manta, Stella</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Dimopoulou, Athina</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Parmenopoulou, Vanessa</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Triantakonstanti, Virginia V</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Kellici, Tahsin</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Mavromoustakos, Thomas</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Schols, Dominique</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Komiotis, Dimitri</subfield><subfield code="4">oth</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">Enthalten in</subfield><subfield code="t">Carbohydrate research</subfield><subfield code="d">Amsterdam : Elsevier, 1965</subfield><subfield code="g">407(2015), Seite 170-178</subfield><subfield code="w">(DE-627)129067776</subfield><subfield code="w">(DE-600)1435-7</subfield><subfield code="w">(DE-576)014399229</subfield><subfield code="x">0008-6215</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:407</subfield><subfield code="g">year:2015</subfield><subfield code="g">pages:170-178</subfield></datafield><datafield tag="856" ind1="4" ind2="1"><subfield code="u">http://dx.doi.org/10.1016/j.carres.2015.01.021</subfield><subfield code="3">Volltext</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="u">http://www.ncbi.nlm.nih.gov/pubmed/25812993</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_OLC</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-TEC</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-CHE</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-PHA</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-DE-84</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_70</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4012</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4305</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">407</subfield><subfield code="j">2015</subfield><subfield code="h">170-178</subfield></datafield></record></collection>
|
| score |
7.398837 |