New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities
A new series of 3-substituted-2,1-benzisoxazoles (anthranils) were prepared by different methods and characterized by spectroscopic methods and mass spectrometry. These 2,1-benzisoxazoles were tested in vitro for their antiplasmodial activity on a chloroquine-resistant strain of Plasmodium falciparu...
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| Format: | Article |
| Language: | English |
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Elsevier
2017-05-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535213003092 |
| _version_ | 1818486672287858688 |
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| author | Aida Chaker Ennaji Najahi Olivier Chatriant Alexis Valentin Nathan Téné Michel Treilhou Fakher Chabchoub Françoise Nepveu |
| author_facet | Aida Chaker Ennaji Najahi Olivier Chatriant Alexis Valentin Nathan Téné Michel Treilhou Fakher Chabchoub Françoise Nepveu |
| author_sort | Aida Chaker |
| collection | DOAJ |
| description | A new series of 3-substituted-2,1-benzisoxazoles (anthranils) were prepared by different methods and characterized by spectroscopic methods and mass spectrometry. These 2,1-benzisoxazoles were tested in vitro for their antiplasmodial activity on a chloroquine-resistant strain of Plasmodium falciparum (P.f.) (FcB1), and for antimicrobial activity against representative bacterial and fungal strains, as well as for cytotoxicity on MCF7 human breast cancer cells. Given the log Pcalc and selectivity index values (cytotoxicity/antiplasmodial activity ratio), the benzo[c]isoxazol-3-ylmethylene-phenyl-amine (11) (imino-benzisoxazole) was identified as the best hit against P.f. (FcB1), and the benzo[c]isoxazol-3-yl-phenyl-methanone (3) (3-acyl-2,1-benzisoxazole) against P.f. and the Geotrichum candidum fungal strain. |
| first_indexed | 2024-12-10T16:26:13Z |
| format | Article |
| id | doaj.art-c2e4456d4fd54f79b86241bdd3caaf5e |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-10T16:26:13Z |
| publishDate | 2017-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-c2e4456d4fd54f79b86241bdd3caaf5e2022-12-22T01:41:39ZengElsevierArabian Journal of Chemistry1878-53522017-05-0110S2S2464S247010.1016/j.arabjc.2013.09.011New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activitiesAida Chaker0Ennaji Najahi1Olivier Chatriant2Alexis Valentin3Nathan Téné4Michel Treilhou5Fakher Chabchoub6Françoise Nepveu7University of Toulouse III, UPS, UMR 152 PHARMA-DEV, 118 Route de Narbonne, F-31062 Toulouse cedex 9, FranceUniversity of Toulouse III, UPS, UMR 152 PHARMA-DEV, 118 Route de Narbonne, F-31062 Toulouse cedex 9, FranceUniversity of Toulouse III, UPS, UMR 152 PHARMA-DEV, 118 Route de Narbonne, F-31062 Toulouse cedex 9, FranceUniversity of Toulouse III, UPS, UMR 152 PHARMA-DEV, 118 Route de Narbonne, F-31062 Toulouse cedex 9, FranceUniversity of Toulouse III, CUFR JF Champollion, EA 4357, Place de Verdun, F-81012 Albi, FranceUniversity of Toulouse III, CUFR JF Champollion, EA 4357, Place de Verdun, F-81012 Albi, FranceUniversity of Sfax, Faculty of Science, Laboratory of Applied Chemistry, 3000 Sfax, TunisiaUniversity of Toulouse III, UPS, UMR 152 PHARMA-DEV, 118 Route de Narbonne, F-31062 Toulouse cedex 9, FranceA new series of 3-substituted-2,1-benzisoxazoles (anthranils) were prepared by different methods and characterized by spectroscopic methods and mass spectrometry. These 2,1-benzisoxazoles were tested in vitro for their antiplasmodial activity on a chloroquine-resistant strain of Plasmodium falciparum (P.f.) (FcB1), and for antimicrobial activity against representative bacterial and fungal strains, as well as for cytotoxicity on MCF7 human breast cancer cells. Given the log Pcalc and selectivity index values (cytotoxicity/antiplasmodial activity ratio), the benzo[c]isoxazol-3-ylmethylene-phenyl-amine (11) (imino-benzisoxazole) was identified as the best hit against P.f. (FcB1), and the benzo[c]isoxazol-3-yl-phenyl-methanone (3) (3-acyl-2,1-benzisoxazole) against P.f. and the Geotrichum candidum fungal strain.http://www.sciencedirect.com/science/article/pii/S18785352130030922,1-BenzisoxazoleAnthranilAntiplasmodialAntimicrobial |
| spellingShingle | Aida Chaker Ennaji Najahi Olivier Chatriant Alexis Valentin Nathan Téné Michel Treilhou Fakher Chabchoub Françoise Nepveu New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities Arabian Journal of Chemistry 2,1-Benzisoxazole Anthranil Antiplasmodial Antimicrobial |
| title | New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities |
| title_full | New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities |
| title_fullStr | New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities |
| title_full_unstemmed | New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities |
| title_short | New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities |
| title_sort | new 3 substituted 2 1 benzisoxazoles synthesis and antimicrobial activities |
| topic | 2,1-Benzisoxazole Anthranil Antiplasmodial Antimicrobial |
| url | http://www.sciencedirect.com/science/article/pii/S1878535213003092 |
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