Synthesis, crystal structure and biological activity of new phosphoester-

Bis(4-(methoxycarbonyl)phenyl)phosphonate and bis(4-(methoxycarbonyl)phenyl) phosphate were prepared from the reaction of p-hydroxybenzoate with phenyl phosphonic dichloride and with phenyl dichlorophosphate, respectively, in the presence of CuCl as catalyst. The structure of the synthesized compoun...
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Gespeichert in:

Autor*in:	Serbezeanu, Diana [verfasserIn] Carja, Ionela-Daniela [verfasserIn] Nicolescu, Alina [verfasserIn] Aflori, Magdalena [verfasserIn] Vlad-Bubulac, Tăchiță [verfasserIn] Butnaru, Maria [verfasserIn] Damian, Radu-Florin [verfasserIn] Dunca, Simona [verfasserIn] Shova, Sergiu [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2019

Schlagwörter:	Crystal structure Single-crystal X-ray diffraction Powder X-ray diffraction MTT

Übergeordnetes Werk:	Enthalten in: Journal of molecular structure - New York, NY [u.a.] : Elsevier, 1967, 1196, Seite 637-646
Übergeordnetes Werk:	volume:1196 ; pages:637-646

DOI / URN:	10.1016/j.molstruc.2019.07.001

Katalog-ID:	ELV00278307X

Internformat


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520			\|a Bis(4-(methoxycarbonyl)phenyl)phosphonate and bis(4-(methoxycarbonyl)phenyl) phosphate were prepared from the reaction of p-hydroxybenzoate with phenyl phosphonic dichloride and with phenyl dichlorophosphate, respectively, in the presence of CuCl as catalyst. The structure of the synthesized compounds was elucidated by FTIR, 1H NMR,13C NMR and 31P NMR spectroscopy. The assignments for the 1H, 13C and 31P chemical shifts are based on 1D and 2D NMR homo- and heteronuclear correlations (H,H-COSY (Correlation Spectroscopy), H,C-HMQC (Heteronuclear Multiple Quantum Correlation and H,C-HMBC (Heteronuclear Multiple Bond Correlation)) and 31P-13C couplings. The synthesized compounds revealed good solubility in common organic solvents. The crystal structure of the products was investigated by single-crystal X-ray diffraction, while the purity of the bulk product was confirmed by powder X-ray diffraction. The antimicrobial effect of the non-phosphoester-functionalized and phosphoester-functionalized p-hydroxybenzoate disc samples was investigated. Antimicrobial activities were evaluated against bacterial strains of Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and fungi Candida a lbicans ATCC 10321 used in this research. The non-phosphoester-functionalized p-hydroxybenzoate exhibit good antibacterial and antifungal effect compared to phosphoester-functionalized p-hydroxybenzoates. The synthesized compounds were screened in vitro for their cytotoxicity on primary Albino Rabbit dermal fibroblasts, by the 3-(4, 5-dimethyl-thiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) protocol. The results showed clearly that the synthesized phosphoesters promote cell viability and they have the potential to be developed into economical and reliable additives for skin cosmetics and pharmaceuticals.
650		4	\|a Crystal structure
650		4	\|a Single-crystal X-ray diffraction
650		4	\|a Powder X-ray diffraction
650		4	\|a MTT
700	1		\|a Carja, Ionela-Daniela \|e verfasserin \|4 aut
700	1		\|a Nicolescu, Alina \|e verfasserin \|4 aut
700	1		\|a Aflori, Magdalena \|e verfasserin \|0 (orcid)0000-0001-5919-221X \|4 aut
700	1		\|a Vlad-Bubulac, Tăchiță \|e verfasserin \|4 aut
700	1		\|a Butnaru, Maria \|e verfasserin \|4 aut
700	1		\|a Damian, Radu-Florin \|e verfasserin \|4 aut
700	1		\|a Dunca, Simona \|e verfasserin \|4 aut
700	1		\|a Shova, Sergiu \|e verfasserin \|4 aut
773	0	8	\|i Enthalten in \|t Journal of molecular structure \|d New York, NY [u.a.] : Elsevier, 1967 \|g 1196, Seite 637-646 \|h Online-Ressource \|w (DE-627)302469745 \|w (DE-600)1491504-2 \|w (DE-576)255266626 \|x 0022-2860 \|7 nnns
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912			\|a GBV_ILN_62
912			\|a GBV_ILN_63
912			\|a GBV_ILN_65
912			\|a GBV_ILN_69
912			\|a GBV_ILN_70
912			\|a GBV_ILN_73
912			\|a GBV_ILN_74
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912			\|a GBV_ILN_95
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912			\|a GBV_ILN_370
912			\|a GBV_ILN_602
912			\|a GBV_ILN_702
912			\|a GBV_ILN_2003
912			\|a GBV_ILN_2004
912			\|a GBV_ILN_2005
912			\|a GBV_ILN_2011
912			\|a GBV_ILN_2014
912			\|a GBV_ILN_2015
912			\|a GBV_ILN_2020
912			\|a GBV_ILN_2021
912			\|a GBV_ILN_2025
912			\|a GBV_ILN_2027
912			\|a GBV_ILN_2034
912			\|a GBV_ILN_2038
912			\|a GBV_ILN_2044
912			\|a GBV_ILN_2048
912			\|a GBV_ILN_2049
912			\|a GBV_ILN_2050
912			\|a GBV_ILN_2056
912			\|a GBV_ILN_2059
912			\|a GBV_ILN_2061
912			\|a GBV_ILN_2064
912			\|a GBV_ILN_2065
912			\|a GBV_ILN_2068
912			\|a GBV_ILN_2111
912			\|a GBV_ILN_2112
912			\|a GBV_ILN_2113
912			\|a GBV_ILN_2118
912			\|a GBV_ILN_2122
912			\|a GBV_ILN_2129
912			\|a GBV_ILN_2143
912			\|a GBV_ILN_2147
912			\|a GBV_ILN_2148
912			\|a GBV_ILN_2152
912			\|a GBV_ILN_2153
912			\|a GBV_ILN_2190
912			\|a GBV_ILN_2336
912			\|a GBV_ILN_2507
912			\|a GBV_ILN_2522
912			\|a GBV_ILN_4035
912			\|a GBV_ILN_4037
912			\|a GBV_ILN_4112
912			\|a GBV_ILN_4125
912			\|a GBV_ILN_4126
912			\|a GBV_ILN_4242
912			\|a GBV_ILN_4251
912			\|a GBV_ILN_4305
912			\|a GBV_ILN_4313
912			\|a GBV_ILN_4323
912			\|a GBV_ILN_4324
912			\|a GBV_ILN_4326
912			\|a GBV_ILN_4333
912			\|a GBV_ILN_4334
912			\|a GBV_ILN_4335
912			\|a GBV_ILN_4338
912			\|a GBV_ILN_4393
936	b	k	\|a 35.00 \|j Chemie: Allgemeines
951			\|a AR
952			\|d 1196 \|h 637-646

Indexfelder

author_variant	d s ds i d c idc a n an m a ma t v b tvb m b mb r f d rfd s d sd s s ss
matchkey_str	article:00222860:2019----::yteicytltutradilgclcii
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publishDate	2019
allfields	10.1016/j.molstruc.2019.07.001 doi (DE-627)ELV00278307X (ELSEVIER)S0022-2860(19)30835-X DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Serbezeanu, Diana verfasserin aut Synthesis, crystal structure and biological activity of new phosphoester- 2019 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Bis(4-(methoxycarbonyl)phenyl)phosphonate and bis(4-(methoxycarbonyl)phenyl) phosphate were prepared from the reaction of p-hydroxybenzoate with phenyl phosphonic dichloride and with phenyl dichlorophosphate, respectively, in the presence of CuCl as catalyst. The structure of the synthesized compounds was elucidated by FTIR, 1H NMR,13C NMR and 31P NMR spectroscopy. The assignments for the 1H, 13C and 31P chemical shifts are based on 1D and 2D NMR homo- and heteronuclear correlations (H,H-COSY (Correlation Spectroscopy), H,C-HMQC (Heteronuclear Multiple Quantum Correlation and H,C-HMBC (Heteronuclear Multiple Bond Correlation)) and 31P-13C couplings. The synthesized compounds revealed good solubility in common organic solvents. The crystal structure of the products was investigated by single-crystal X-ray diffraction, while the purity of the bulk product was confirmed by powder X-ray diffraction. The antimicrobial effect of the non-phosphoester-functionalized and phosphoester-functionalized p-hydroxybenzoate disc samples was investigated. Antimicrobial activities were evaluated against bacterial strains of Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and fungi Candida a lbicans ATCC 10321 used in this research. The non-phosphoester-functionalized p-hydroxybenzoate exhibit good antibacterial and antifungal effect compared to phosphoester-functionalized p-hydroxybenzoates. The synthesized compounds were screened in vitro for their cytotoxicity on primary Albino Rabbit dermal fibroblasts, by the 3-(4, 5-dimethyl-thiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) protocol. The results showed clearly that the synthesized phosphoesters promote cell viability and they have the potential to be developed into economical and reliable additives for skin cosmetics and pharmaceuticals. Crystal structure Single-crystal X-ray diffraction Powder X-ray diffraction MTT Carja, Ionela-Daniela verfasserin aut Nicolescu, Alina verfasserin aut Aflori, Magdalena verfasserin (orcid)0000-0001-5919-221X aut Vlad-Bubulac, Tăchiță verfasserin aut Butnaru, Maria verfasserin aut Damian, Radu-Florin verfasserin aut Dunca, Simona verfasserin aut Shova, Sergiu verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1196, Seite 637-646 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1196 pages:637-646 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.00 Chemie: Allgemeines AR 1196 637-646
spelling	10.1016/j.molstruc.2019.07.001 doi (DE-627)ELV00278307X (ELSEVIER)S0022-2860(19)30835-X DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Serbezeanu, Diana verfasserin aut Synthesis, crystal structure and biological activity of new phosphoester- 2019 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Bis(4-(methoxycarbonyl)phenyl)phosphonate and bis(4-(methoxycarbonyl)phenyl) phosphate were prepared from the reaction of p-hydroxybenzoate with phenyl phosphonic dichloride and with phenyl dichlorophosphate, respectively, in the presence of CuCl as catalyst. The structure of the synthesized compounds was elucidated by FTIR, 1H NMR,13C NMR and 31P NMR spectroscopy. The assignments for the 1H, 13C and 31P chemical shifts are based on 1D and 2D NMR homo- and heteronuclear correlations (H,H-COSY (Correlation Spectroscopy), H,C-HMQC (Heteronuclear Multiple Quantum Correlation and H,C-HMBC (Heteronuclear Multiple Bond Correlation)) and 31P-13C couplings. The synthesized compounds revealed good solubility in common organic solvents. The crystal structure of the products was investigated by single-crystal X-ray diffraction, while the purity of the bulk product was confirmed by powder X-ray diffraction. The antimicrobial effect of the non-phosphoester-functionalized and phosphoester-functionalized p-hydroxybenzoate disc samples was investigated. Antimicrobial activities were evaluated against bacterial strains of Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and fungi Candida a lbicans ATCC 10321 used in this research. The non-phosphoester-functionalized p-hydroxybenzoate exhibit good antibacterial and antifungal effect compared to phosphoester-functionalized p-hydroxybenzoates. The synthesized compounds were screened in vitro for their cytotoxicity on primary Albino Rabbit dermal fibroblasts, by the 3-(4, 5-dimethyl-thiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) protocol. The results showed clearly that the synthesized phosphoesters promote cell viability and they have the potential to be developed into economical and reliable additives for skin cosmetics and pharmaceuticals. Crystal structure Single-crystal X-ray diffraction Powder X-ray diffraction MTT Carja, Ionela-Daniela verfasserin aut Nicolescu, Alina verfasserin aut Aflori, Magdalena verfasserin (orcid)0000-0001-5919-221X aut Vlad-Bubulac, Tăchiță verfasserin aut Butnaru, Maria verfasserin aut Damian, Radu-Florin verfasserin aut Dunca, Simona verfasserin aut Shova, Sergiu verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1196, Seite 637-646 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1196 pages:637-646 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.00 Chemie: Allgemeines AR 1196 637-646
allfields_unstemmed	10.1016/j.molstruc.2019.07.001 doi (DE-627)ELV00278307X (ELSEVIER)S0022-2860(19)30835-X DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Serbezeanu, Diana verfasserin aut Synthesis, crystal structure and biological activity of new phosphoester- 2019 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Bis(4-(methoxycarbonyl)phenyl)phosphonate and bis(4-(methoxycarbonyl)phenyl) phosphate were prepared from the reaction of p-hydroxybenzoate with phenyl phosphonic dichloride and with phenyl dichlorophosphate, respectively, in the presence of CuCl as catalyst. The structure of the synthesized compounds was elucidated by FTIR, 1H NMR,13C NMR and 31P NMR spectroscopy. The assignments for the 1H, 13C and 31P chemical shifts are based on 1D and 2D NMR homo- and heteronuclear correlations (H,H-COSY (Correlation Spectroscopy), H,C-HMQC (Heteronuclear Multiple Quantum Correlation and H,C-HMBC (Heteronuclear Multiple Bond Correlation)) and 31P-13C couplings. The synthesized compounds revealed good solubility in common organic solvents. The crystal structure of the products was investigated by single-crystal X-ray diffraction, while the purity of the bulk product was confirmed by powder X-ray diffraction. The antimicrobial effect of the non-phosphoester-functionalized and phosphoester-functionalized p-hydroxybenzoate disc samples was investigated. Antimicrobial activities were evaluated against bacterial strains of Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and fungi Candida a lbicans ATCC 10321 used in this research. The non-phosphoester-functionalized p-hydroxybenzoate exhibit good antibacterial and antifungal effect compared to phosphoester-functionalized p-hydroxybenzoates. The synthesized compounds were screened in vitro for their cytotoxicity on primary Albino Rabbit dermal fibroblasts, by the 3-(4, 5-dimethyl-thiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) protocol. The results showed clearly that the synthesized phosphoesters promote cell viability and they have the potential to be developed into economical and reliable additives for skin cosmetics and pharmaceuticals. Crystal structure Single-crystal X-ray diffraction Powder X-ray diffraction MTT Carja, Ionela-Daniela verfasserin aut Nicolescu, Alina verfasserin aut Aflori, Magdalena verfasserin (orcid)0000-0001-5919-221X aut Vlad-Bubulac, Tăchiță verfasserin aut Butnaru, Maria verfasserin aut Damian, Radu-Florin verfasserin aut Dunca, Simona verfasserin aut Shova, Sergiu verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1196, Seite 637-646 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1196 pages:637-646 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.00 Chemie: Allgemeines AR 1196 637-646
allfieldsGer	10.1016/j.molstruc.2019.07.001 doi (DE-627)ELV00278307X (ELSEVIER)S0022-2860(19)30835-X DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Serbezeanu, Diana verfasserin aut Synthesis, crystal structure and biological activity of new phosphoester- 2019 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Bis(4-(methoxycarbonyl)phenyl)phosphonate and bis(4-(methoxycarbonyl)phenyl) phosphate were prepared from the reaction of p-hydroxybenzoate with phenyl phosphonic dichloride and with phenyl dichlorophosphate, respectively, in the presence of CuCl as catalyst. The structure of the synthesized compounds was elucidated by FTIR, 1H NMR,13C NMR and 31P NMR spectroscopy. The assignments for the 1H, 13C and 31P chemical shifts are based on 1D and 2D NMR homo- and heteronuclear correlations (H,H-COSY (Correlation Spectroscopy), H,C-HMQC (Heteronuclear Multiple Quantum Correlation and H,C-HMBC (Heteronuclear Multiple Bond Correlation)) and 31P-13C couplings. The synthesized compounds revealed good solubility in common organic solvents. The crystal structure of the products was investigated by single-crystal X-ray diffraction, while the purity of the bulk product was confirmed by powder X-ray diffraction. The antimicrobial effect of the non-phosphoester-functionalized and phosphoester-functionalized p-hydroxybenzoate disc samples was investigated. Antimicrobial activities were evaluated against bacterial strains of Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and fungi Candida a lbicans ATCC 10321 used in this research. The non-phosphoester-functionalized p-hydroxybenzoate exhibit good antibacterial and antifungal effect compared to phosphoester-functionalized p-hydroxybenzoates. The synthesized compounds were screened in vitro for their cytotoxicity on primary Albino Rabbit dermal fibroblasts, by the 3-(4, 5-dimethyl-thiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) protocol. The results showed clearly that the synthesized phosphoesters promote cell viability and they have the potential to be developed into economical and reliable additives for skin cosmetics and pharmaceuticals. Crystal structure Single-crystal X-ray diffraction Powder X-ray diffraction MTT Carja, Ionela-Daniela verfasserin aut Nicolescu, Alina verfasserin aut Aflori, Magdalena verfasserin (orcid)0000-0001-5919-221X aut Vlad-Bubulac, Tăchiță verfasserin aut Butnaru, Maria verfasserin aut Damian, Radu-Florin verfasserin aut Dunca, Simona verfasserin aut Shova, Sergiu verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1196, Seite 637-646 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1196 pages:637-646 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.00 Chemie: Allgemeines AR 1196 637-646
allfieldsSound	10.1016/j.molstruc.2019.07.001 doi (DE-627)ELV00278307X (ELSEVIER)S0022-2860(19)30835-X DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Serbezeanu, Diana verfasserin aut Synthesis, crystal structure and biological activity of new phosphoester- 2019 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Bis(4-(methoxycarbonyl)phenyl)phosphonate and bis(4-(methoxycarbonyl)phenyl) phosphate were prepared from the reaction of p-hydroxybenzoate with phenyl phosphonic dichloride and with phenyl dichlorophosphate, respectively, in the presence of CuCl as catalyst. The structure of the synthesized compounds was elucidated by FTIR, 1H NMR,13C NMR and 31P NMR spectroscopy. The assignments for the 1H, 13C and 31P chemical shifts are based on 1D and 2D NMR homo- and heteronuclear correlations (H,H-COSY (Correlation Spectroscopy), H,C-HMQC (Heteronuclear Multiple Quantum Correlation and H,C-HMBC (Heteronuclear Multiple Bond Correlation)) and 31P-13C couplings. The synthesized compounds revealed good solubility in common organic solvents. The crystal structure of the products was investigated by single-crystal X-ray diffraction, while the purity of the bulk product was confirmed by powder X-ray diffraction. The antimicrobial effect of the non-phosphoester-functionalized and phosphoester-functionalized p-hydroxybenzoate disc samples was investigated. Antimicrobial activities were evaluated against bacterial strains of Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and fungi Candida a lbicans ATCC 10321 used in this research. The non-phosphoester-functionalized p-hydroxybenzoate exhibit good antibacterial and antifungal effect compared to phosphoester-functionalized p-hydroxybenzoates. The synthesized compounds were screened in vitro for their cytotoxicity on primary Albino Rabbit dermal fibroblasts, by the 3-(4, 5-dimethyl-thiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) protocol. The results showed clearly that the synthesized phosphoesters promote cell viability and they have the potential to be developed into economical and reliable additives for skin cosmetics and pharmaceuticals. Crystal structure Single-crystal X-ray diffraction Powder X-ray diffraction MTT Carja, Ionela-Daniela verfasserin aut Nicolescu, Alina verfasserin aut Aflori, Magdalena verfasserin (orcid)0000-0001-5919-221X aut Vlad-Bubulac, Tăchiță verfasserin aut Butnaru, Maria verfasserin aut Damian, Radu-Florin verfasserin aut Dunca, Simona verfasserin aut Shova, Sergiu verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1196, Seite 637-646 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1196 pages:637-646 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.00 Chemie: Allgemeines AR 1196 637-646
language	English
source	Enthalten in Journal of molecular structure 1196, Seite 637-646 volume:1196 pages:637-646
sourceStr	Enthalten in Journal of molecular structure 1196, Seite 637-646 volume:1196 pages:637-646
format_phy_str_mv	Article
bklname	Chemie: Allgemeines
institution	findex.gbv.de
topic_facet	Crystal structure Single-crystal X-ray diffraction Powder X-ray diffraction MTT
dewey-raw	540
isfreeaccess_bool	false
container_title	Journal of molecular structure
authorswithroles_txt_mv	Serbezeanu, Diana @@aut@@ Carja, Ionela-Daniela @@aut@@ Nicolescu, Alina @@aut@@ Aflori, Magdalena @@aut@@ Vlad-Bubulac, Tăchiță @@aut@@ Butnaru, Maria @@aut@@ Damian, Radu-Florin @@aut@@ Dunca, Simona @@aut@@ Shova, Sergiu @@aut@@
publishDateDaySort_date	2019-01-01T00:00:00Z
hierarchy_top_id	302469745
dewey-sort	3540
id	ELV00278307X
language_de	englisch
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author	Serbezeanu, Diana
spellingShingle	Serbezeanu, Diana ddc 540 bkl 35.00 misc Crystal structure misc Single-crystal X-ray diffraction misc Powder X-ray diffraction misc MTT Synthesis, crystal structure and biological activity of new phosphoester-
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topic_title	540 DE-600 35.00 bkl Synthesis, crystal structure and biological activity of new phosphoester- Crystal structure Single-crystal X-ray diffraction Powder X-ray diffraction MTT
topic	ddc 540 bkl 35.00 misc Crystal structure misc Single-crystal X-ray diffraction misc Powder X-ray diffraction misc MTT
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title	Synthesis, crystal structure and biological activity of new phosphoester-
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title_full	Synthesis, crystal structure and biological activity of new phosphoester-
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author_browse	Serbezeanu, Diana Carja, Ionela-Daniela Nicolescu, Alina Aflori, Magdalena Vlad-Bubulac, Tăchiță Butnaru, Maria Damian, Radu-Florin Dunca, Simona Shova, Sergiu
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title_sort	synthesis, crystal structure and biological activity of new phosphoester-
title_auth	Synthesis, crystal structure and biological activity of new phosphoester-
abstract	Bis(4-(methoxycarbonyl)phenyl)phosphonate and bis(4-(methoxycarbonyl)phenyl) phosphate were prepared from the reaction of p-hydroxybenzoate with phenyl phosphonic dichloride and with phenyl dichlorophosphate, respectively, in the presence of CuCl as catalyst. The structure of the synthesized compounds was elucidated by FTIR, 1H NMR,13C NMR and 31P NMR spectroscopy. The assignments for the 1H, 13C and 31P chemical shifts are based on 1D and 2D NMR homo- and heteronuclear correlations (H,H-COSY (Correlation Spectroscopy), H,C-HMQC (Heteronuclear Multiple Quantum Correlation and H,C-HMBC (Heteronuclear Multiple Bond Correlation)) and 31P-13C couplings. The synthesized compounds revealed good solubility in common organic solvents. The crystal structure of the products was investigated by single-crystal X-ray diffraction, while the purity of the bulk product was confirmed by powder X-ray diffraction. The antimicrobial effect of the non-phosphoester-functionalized and phosphoester-functionalized p-hydroxybenzoate disc samples was investigated. Antimicrobial activities were evaluated against bacterial strains of Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and fungi Candida a lbicans ATCC 10321 used in this research. The non-phosphoester-functionalized p-hydroxybenzoate exhibit good antibacterial and antifungal effect compared to phosphoester-functionalized p-hydroxybenzoates. The synthesized compounds were screened in vitro for their cytotoxicity on primary Albino Rabbit dermal fibroblasts, by the 3-(4, 5-dimethyl-thiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) protocol. The results showed clearly that the synthesized phosphoesters promote cell viability and they have the potential to be developed into economical and reliable additives for skin cosmetics and pharmaceuticals.
abstractGer	Bis(4-(methoxycarbonyl)phenyl)phosphonate and bis(4-(methoxycarbonyl)phenyl) phosphate were prepared from the reaction of p-hydroxybenzoate with phenyl phosphonic dichloride and with phenyl dichlorophosphate, respectively, in the presence of CuCl as catalyst. The structure of the synthesized compounds was elucidated by FTIR, 1H NMR,13C NMR and 31P NMR spectroscopy. The assignments for the 1H, 13C and 31P chemical shifts are based on 1D and 2D NMR homo- and heteronuclear correlations (H,H-COSY (Correlation Spectroscopy), H,C-HMQC (Heteronuclear Multiple Quantum Correlation and H,C-HMBC (Heteronuclear Multiple Bond Correlation)) and 31P-13C couplings. The synthesized compounds revealed good solubility in common organic solvents. The crystal structure of the products was investigated by single-crystal X-ray diffraction, while the purity of the bulk product was confirmed by powder X-ray diffraction. The antimicrobial effect of the non-phosphoester-functionalized and phosphoester-functionalized p-hydroxybenzoate disc samples was investigated. Antimicrobial activities were evaluated against bacterial strains of Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and fungi Candida a lbicans ATCC 10321 used in this research. The non-phosphoester-functionalized p-hydroxybenzoate exhibit good antibacterial and antifungal effect compared to phosphoester-functionalized p-hydroxybenzoates. The synthesized compounds were screened in vitro for their cytotoxicity on primary Albino Rabbit dermal fibroblasts, by the 3-(4, 5-dimethyl-thiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) protocol. The results showed clearly that the synthesized phosphoesters promote cell viability and they have the potential to be developed into economical and reliable additives for skin cosmetics and pharmaceuticals.
abstract_unstemmed	Bis(4-(methoxycarbonyl)phenyl)phosphonate and bis(4-(methoxycarbonyl)phenyl) phosphate were prepared from the reaction of p-hydroxybenzoate with phenyl phosphonic dichloride and with phenyl dichlorophosphate, respectively, in the presence of CuCl as catalyst. The structure of the synthesized compounds was elucidated by FTIR, 1H NMR,13C NMR and 31P NMR spectroscopy. The assignments for the 1H, 13C and 31P chemical shifts are based on 1D and 2D NMR homo- and heteronuclear correlations (H,H-COSY (Correlation Spectroscopy), H,C-HMQC (Heteronuclear Multiple Quantum Correlation and H,C-HMBC (Heteronuclear Multiple Bond Correlation)) and 31P-13C couplings. The synthesized compounds revealed good solubility in common organic solvents. The crystal structure of the products was investigated by single-crystal X-ray diffraction, while the purity of the bulk product was confirmed by powder X-ray diffraction. The antimicrobial effect of the non-phosphoester-functionalized and phosphoester-functionalized p-hydroxybenzoate disc samples was investigated. Antimicrobial activities were evaluated against bacterial strains of Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and fungi Candida a lbicans ATCC 10321 used in this research. The non-phosphoester-functionalized p-hydroxybenzoate exhibit good antibacterial and antifungal effect compared to phosphoester-functionalized p-hydroxybenzoates. The synthesized compounds were screened in vitro for their cytotoxicity on primary Albino Rabbit dermal fibroblasts, by the 3-(4, 5-dimethyl-thiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) protocol. The results showed clearly that the synthesized phosphoesters promote cell viability and they have the potential to be developed into economical and reliable additives for skin cosmetics and pharmaceuticals.
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title_short	Synthesis, crystal structure and biological activity of new phosphoester-
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author2	Carja, Ionela-Daniela Nicolescu, Alina Aflori, Magdalena Vlad-Bubulac, Tăchiță Butnaru, Maria Damian, Radu-Florin Dunca, Simona Shova, Sergiu
author2Str	Carja, Ionela-Daniela Nicolescu, Alina Aflori, Magdalena Vlad-Bubulac, Tăchiță Butnaru, Maria Damian, Radu-Florin Dunca, Simona Shova, Sergiu
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doi_str	10.1016/j.molstruc.2019.07.001
up_date	2024-07-06T17:26:07.676Z
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The structure of the synthesized compounds was elucidated by FTIR, 1H NMR,13C NMR and 31P NMR spectroscopy. The assignments for the 1H, 13C and 31P chemical shifts are based on 1D and 2D NMR homo- and heteronuclear correlations (H,H-COSY (Correlation Spectroscopy), H,C-HMQC (Heteronuclear Multiple Quantum Correlation and H,C-HMBC (Heteronuclear Multiple Bond Correlation)) and 31P-13C couplings. The synthesized compounds revealed good solubility in common organic solvents. The crystal structure of the products was investigated by single-crystal X-ray diffraction, while the purity of the bulk product was confirmed by powder X-ray diffraction. The antimicrobial effect of the non-phosphoester-functionalized and phosphoester-functionalized p-hydroxybenzoate disc samples was investigated. Antimicrobial activities were evaluated against bacterial strains of Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and fungi Candida a lbicans ATCC 10321 used in this research. The non-phosphoester-functionalized p-hydroxybenzoate exhibit good antibacterial and antifungal effect compared to phosphoester-functionalized p-hydroxybenzoates. The synthesized compounds were screened in vitro for their cytotoxicity on primary Albino Rabbit dermal fibroblasts, by the 3-(4, 5-dimethyl-thiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) protocol. The results showed clearly that the synthesized phosphoesters promote cell viability and they have the potential to be developed into economical and reliable additives for skin cosmetics and pharmaceuticals.</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Crystal structure</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Single-crystal X-ray diffraction</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Powder X-ray diffraction</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">MTT</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Carja, Ionela-Daniela</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Nicolescu, Alina</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" 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