New groups of antimycobacterial agents: 6-chloro-3-phenyl-4-thioxo-2 -1,3-benzoxazine-2(3 )-ones and 6-chloro-3-phenyl-2 -1,3-benzoxazine-2,4(3 )-dithiones
| Autor: | Jarmila Kaustová, Jiri Kunes, Vera Klimesova, Lenka Kubicová, Karel Waisser, Miloš Macháček, Jiří Gregor |
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| Rok vydání: | 2000 |
| Předmět: |
Pharmacology
Quantitative structure–activity relationship Bicyclic molecule Antimycobacterial Agents Stereochemistry Chemistry Organic Chemistry Isoniazid Microbial Sensitivity Tests General Medicine Ring (chemistry) Chemical synthesis Anti-Bacterial Agents Mycobacterium Species Specificity Oxazines Drug Discovery Benzene derivatives medicine Antibacterial agent medicine.drug |
| Zdroj: | European Journal of Medicinal Chemistry. 35:733-741 |
| ISSN: | 0223-5234 |
| Popis: | A series of 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones 3 and a series of 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones 4 were synthesized by melting 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dione and its derivatives substituted on the phenyl ring 2 with tetraphosphorus decasulfide. Compounds 2c–e, 3 and 4 exhibited in vitro activity against Mycobacterium tuberculosis, M. kansasii (two strains) and M. avium better than or comparable to that of isoniazid. Replacement of the oxo group by a thioxo group at position 4 led to improvement in activity against M. tuberculosis and M. kansasii. The Free-Wilson method and procedure developed by the authors were used to analyse the structure–activity and structure–antimycobacterial profile relationships, respectively. |
| Databáze: | OpenAIRE |
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