A novel and easy two-step, microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. Evaluation of their bioactivity
Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihy...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Manta, Stella [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2014transfer abstract |
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| Schlagwörter: |
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| Umfang: |
4 |
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| Übergeordnetes Werk: |
Enthalten in: Continuing Medical Education Program - 2013, Amsterdam [u.a.] |
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| Übergeordnetes Werk: |
volume:55 ; year:2014 ; number:11 ; day:12 ; month:03 ; pages:1873-1876 ; extent:4 |
| Links: |
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| DOI / URN: |
10.1016/j.tetlet.2014.01.106 |
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ELV022364625 |
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| 245 | 1 | 0 | |a A novel and easy two-step, microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. Evaluation of their bioactivity |
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| 520 | |a Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. | ||
| 520 | |a Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. | ||
| 650 | 7 | |a Pyrroloquinoxaline |2 Elsevier | |
| 650 | 7 | |a Multicomponent reaction |2 Elsevier | |
| 650 | 7 | |a Cytostatic activity |2 Elsevier | |
| 650 | 7 | |a Antioxidant activity |2 Elsevier | |
| 650 | 7 | |a Antiviral activity |2 Elsevier | |
| 650 | 7 | |a Pyrrolidine |2 Elsevier | |
| 700 | 1 | |a Gkaragkouni, Dimitra-Niki |4 oth | |
| 700 | 1 | |a Kaffesaki, Eleni |4 oth | |
| 700 | 1 | |a Gkizis, Petros |4 oth | |
| 700 | 1 | |a Hadjipavlou-Litina, Dimitra |4 oth | |
| 700 | 1 | |a Pontiki, Eleni |4 oth | |
| 700 | 1 | |a Balzarini, Jan |4 oth | |
| 700 | 1 | |a Dehaen, Wim |4 oth | |
| 700 | 1 | |a Komiotis, Dimitri |4 oth | |
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10.1016/j.tetlet.2014.01.106 doi GBVA2014001000017.pica (DE-627)ELV022364625 (ELSEVIER)S0040-4039(14)00152-X DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 540 VZ 35.00 bkl Manta, Stella verfasserin aut A novel and easy two-step, microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. Evaluation of their bioactivity 2014transfer abstract 4 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. Pyrroloquinoxaline Elsevier Multicomponent reaction Elsevier Cytostatic activity Elsevier Antioxidant activity Elsevier Antiviral activity Elsevier Pyrrolidine Elsevier Gkaragkouni, Dimitra-Niki oth Kaffesaki, Eleni oth Gkizis, Petros oth Hadjipavlou-Litina, Dimitra oth Pontiki, Eleni oth Balzarini, Jan oth Dehaen, Wim oth Komiotis, Dimitri oth Enthalten in Elsevier Science Continuing Medical Education Program 2013 Amsterdam [u.a.] (DE-627)ELV011942339 volume:55 year:2014 number:11 day:12 month:03 pages:1873-1876 extent:4 https://doi.org/10.1016/j.tetlet.2014.01.106 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.00 Chemie: Allgemeines VZ AR 55 2014 11 12 0312 1873-1876 4 045F 540 |
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10.1016/j.tetlet.2014.01.106 doi GBVA2014001000017.pica (DE-627)ELV022364625 (ELSEVIER)S0040-4039(14)00152-X DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 540 VZ 35.00 bkl Manta, Stella verfasserin aut A novel and easy two-step, microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. Evaluation of their bioactivity 2014transfer abstract 4 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. Pyrroloquinoxaline Elsevier Multicomponent reaction Elsevier Cytostatic activity Elsevier Antioxidant activity Elsevier Antiviral activity Elsevier Pyrrolidine Elsevier Gkaragkouni, Dimitra-Niki oth Kaffesaki, Eleni oth Gkizis, Petros oth Hadjipavlou-Litina, Dimitra oth Pontiki, Eleni oth Balzarini, Jan oth Dehaen, Wim oth Komiotis, Dimitri oth Enthalten in Elsevier Science Continuing Medical Education Program 2013 Amsterdam [u.a.] (DE-627)ELV011942339 volume:55 year:2014 number:11 day:12 month:03 pages:1873-1876 extent:4 https://doi.org/10.1016/j.tetlet.2014.01.106 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.00 Chemie: Allgemeines VZ AR 55 2014 11 12 0312 1873-1876 4 045F 540 |
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10.1016/j.tetlet.2014.01.106 doi GBVA2014001000017.pica (DE-627)ELV022364625 (ELSEVIER)S0040-4039(14)00152-X DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 540 VZ 35.00 bkl Manta, Stella verfasserin aut A novel and easy two-step, microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. Evaluation of their bioactivity 2014transfer abstract 4 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. Pyrroloquinoxaline Elsevier Multicomponent reaction Elsevier Cytostatic activity Elsevier Antioxidant activity Elsevier Antiviral activity Elsevier Pyrrolidine Elsevier Gkaragkouni, Dimitra-Niki oth Kaffesaki, Eleni oth Gkizis, Petros oth Hadjipavlou-Litina, Dimitra oth Pontiki, Eleni oth Balzarini, Jan oth Dehaen, Wim oth Komiotis, Dimitri oth Enthalten in Elsevier Science Continuing Medical Education Program 2013 Amsterdam [u.a.] (DE-627)ELV011942339 volume:55 year:2014 number:11 day:12 month:03 pages:1873-1876 extent:4 https://doi.org/10.1016/j.tetlet.2014.01.106 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.00 Chemie: Allgemeines VZ AR 55 2014 11 12 0312 1873-1876 4 045F 540 |
| allfieldsGer |
10.1016/j.tetlet.2014.01.106 doi GBVA2014001000017.pica (DE-627)ELV022364625 (ELSEVIER)S0040-4039(14)00152-X DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 540 VZ 35.00 bkl Manta, Stella verfasserin aut A novel and easy two-step, microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. Evaluation of their bioactivity 2014transfer abstract 4 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. Pyrroloquinoxaline Elsevier Multicomponent reaction Elsevier Cytostatic activity Elsevier Antioxidant activity Elsevier Antiviral activity Elsevier Pyrrolidine Elsevier Gkaragkouni, Dimitra-Niki oth Kaffesaki, Eleni oth Gkizis, Petros oth Hadjipavlou-Litina, Dimitra oth Pontiki, Eleni oth Balzarini, Jan oth Dehaen, Wim oth Komiotis, Dimitri oth Enthalten in Elsevier Science Continuing Medical Education Program 2013 Amsterdam [u.a.] (DE-627)ELV011942339 volume:55 year:2014 number:11 day:12 month:03 pages:1873-1876 extent:4 https://doi.org/10.1016/j.tetlet.2014.01.106 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.00 Chemie: Allgemeines VZ AR 55 2014 11 12 0312 1873-1876 4 045F 540 |
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10.1016/j.tetlet.2014.01.106 doi GBVA2014001000017.pica (DE-627)ELV022364625 (ELSEVIER)S0040-4039(14)00152-X DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 540 VZ 35.00 bkl Manta, Stella verfasserin aut A novel and easy two-step, microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. Evaluation of their bioactivity 2014transfer abstract 4 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. Pyrroloquinoxaline Elsevier Multicomponent reaction Elsevier Cytostatic activity Elsevier Antioxidant activity Elsevier Antiviral activity Elsevier Pyrrolidine Elsevier Gkaragkouni, Dimitra-Niki oth Kaffesaki, Eleni oth Gkizis, Petros oth Hadjipavlou-Litina, Dimitra oth Pontiki, Eleni oth Balzarini, Jan oth Dehaen, Wim oth Komiotis, Dimitri oth Enthalten in Elsevier Science Continuing Medical Education Program 2013 Amsterdam [u.a.] (DE-627)ELV011942339 volume:55 year:2014 number:11 day:12 month:03 pages:1873-1876 extent:4 https://doi.org/10.1016/j.tetlet.2014.01.106 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.00 Chemie: Allgemeines VZ AR 55 2014 11 12 0312 1873-1876 4 045F 540 |
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a novel and easy two-step, microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. evaluation of their bioactivity |
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A novel and easy two-step, microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. Evaluation of their bioactivity |
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Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. |
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Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. |
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Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM. |
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A novel and easy two-step, microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. Evaluation of their bioactivity |
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The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM.</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">Abstract A novel, two-step, facile route for the synthesis of pyrrolo[2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo[2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4μM.</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Pyrroloquinoxaline</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Multicomponent reaction</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Cytostatic activity</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Antioxidant activity</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Antiviral activity</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Pyrrolidine</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Gkaragkouni, Dimitra-Niki</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Kaffesaki, Eleni</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Gkizis, Petros</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Hadjipavlou-Litina, Dimitra</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Pontiki, Eleni</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Balzarini, Jan</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Dehaen, Wim</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="n">Elsevier Science</subfield><subfield code="t">Continuing Medical Education Program</subfield><subfield code="d">2013</subfield><subfield code="g">Amsterdam [u.a.]</subfield><subfield code="w">(DE-627)ELV011942339</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:55</subfield><subfield code="g">year:2014</subfield><subfield code="g">number:11</subfield><subfield code="g">day:12</subfield><subfield code="g">month:03</subfield><subfield code="g">pages:1873-1876</subfield><subfield code="g">extent:4</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">https://doi.org/10.1016/j.tetlet.2014.01.106</subfield><subfield code="3">Volltext</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ELV</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-PHA</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">35.00</subfield><subfield code="j">Chemie: Allgemeines</subfield><subfield code="q">VZ</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">55</subfield><subfield code="j">2014</subfield><subfield code="e">11</subfield><subfield code="b">12</subfield><subfield code="c">0312</subfield><subfield code="h">1873-1876</subfield><subfield code="g">4</subfield></datafield><datafield tag="953" ind1=" " ind2=" "><subfield code="2">045F</subfield><subfield code="a">540</subfield></datafield></record></collection>
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