Synthesis and HIV-1 reverse transcriptase inhibitor activity of some 2,5,6-substituted benzoxazole, benzimidazole, benzothiazole and oxazolo (4,5-b)pyridine derivatives

Arzneimittel-Forschung/Drug Research

Volumn 53, Issue 4, 2003, Pages 266-271

  Akbay, Ayşegül ^a   Ören, Ilkay ^a   Temiz Arpaci, Özlem ^a   Aki Sener, Esin ^a   Yalçin, Ismail ^a  

^a ANKARA UNIVERSITY   (Turkey)

Author keywords

Antiviral drugs; Benzimidazoles; Benzothiazoles; Benzoxazoles; HIV 1 reverse transcriptase, enzyme inhibitors; Oxazolo(4,5 b)pyridines

Indexed keywords

ANTIVIRUS AGENT; BENZIMIDAZOLE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; DIDEOXYTHYMIDINE TRIPHOSPHATE; PYRIDINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG; ZIDOVUDINE DERIVATIVE; ZIDOVUDINE TRIPHOSPHATE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN IMMUNODEFICIENCY VIRUS 1; REVERSE TRANSCRIPTION; SCINTILLATION;

EID: 0038745928     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1297107     Document Type: Article

References (23)

1. Arranz, M. E. Diaz, J. A. Ingate, S. T. et al., Synthesis and Anti-HIV Activity of 1,1,3-Trioxo-2H,4H-thieno[3,4-e][1,2,4] thiadianes (TTDs): A new Family of HIV-1 Specific Non-Nucleoside Reverse Transcriptase Inhibitors. Bioorg. Med. Chem. 7, 2811 (1999)
2. De Clercq, E., Toward improved Anti-HIV chemotheraphy: Therapeutic Strategies for intervention with HIV infections. J. Med. Chem. 38, 2491 (1995)
3. Tong, W. De Lu, C. Sharma, K. S. et al., Nucleotide-Induced Stable Complex Formation by HIV-1 Reverse Transcriptase. Biochemistry 36, 5749 (1997)
4. Olivo, H. F., Yu, J., Practical enantiodivergent syntheses of both enantiomers of carbovir, 1592U89 and six-membered ring analogues. J. Chem. Soc. Perkin Trans. I, 391 (1998)
5. Uckun, F. M., Mao, C., Pendergrass, S. et al., N[2-(1-cyclohexenyl)ethyl]-N′-[2-(5-bromopyridyl)]-thiourea and N′-[2-(1-cyclohexenyl)ethyl]-N′-[2-(5-chloropyridyl)]-thiourea as potent inhibitors of multidrug-resistant human immunodeficiency virus-1. Bioorg. Med. Chem. 9, 2721 (1999)
6. Badawey, E. A. M., Hazzaa, A. A., Rida, S. M. et al., Assessment of anti-HIV activity of some benzimidazolylthiazoles. Arch. Pharm. (Weinheim) 325, 565 (1992)
7. Balani, S. K., Pitzenberger, S. M., Kauffman, L. R. et al., Metabolism of a new HIV-1 reverse Transcriptase Inhibitor, 3-[2-(Benzoxazol-2-yl)ethyl]-5-ethyl-6-methylpyridin-2(1H)-one (L-696,229). In Rat and Liver Slices. Drug Metab. Dispos.. 20, 869 (1992)
8. Houpis, I. N., Molina, A., Lynch, J. et al., Condensation of 2-Methylbenzoxazole with Aromatic Aldehydes Bearing Acidic Protons. A Convenient Coupling in the Synthesis of HIV-Reverse Transcriptase Inhibitor L-696,229. J. Org. Chem. 58, 3176 (1993)
9. Carroll, S. S., Olsen, D. B., Bennett, C. D. et al., J. Biol. Chem. 268, 276 (1993).
10. Saari, W. S. Wai, J. S., Fisher, T. E. et al., Synthesis and Evaluation of 2-Pyridinone Derivatives as HIV-1 Specific Reverse Transcriptase Inhibitors. 2. Analogues of 3-Aminopyridin-2(1H)-one. J. Med. Chem. 35, 3792 (1992)
11. Davey, R. T., Dewar, R. L., Reed, G. F. et al., Plasma viremia as a sensitive indicator of the antiretroviral activity of L-697, 661. Proc. Natl. Acad. Sci. USA 90, 5608 (1993)
12. Yalçin, İ. Ören, I. Şener, E. et al., The synthesis and the structure-activity relationships of some substituted benzoxazoles, oxazolo(4,5-b)pyridines, benzothiazoles and benzimidazoles as antimicrobial agents. Eur. J. Med. Chem. 27, 568 (1992)
13. King, F. E., Acheson, R. M., The synthesis of benzimidazoles from ortho-phenylenediamines and iminoethers. J. Chem. Soc. 1396 (1949)
14. Gümüş, F., Altuntas T. G., Saygun T. et al., In vitro tuberculostatic activities of some 2-benzylbenzimidazole and 2-phenoxymethylbenzimidazole derivatives. Pharm. Belg. 44, 398 (1989)
15. Ören, İ. Temiz, Ö. Yalçin, I. et al., Synthesis and Microbiological Activity of 5 (or 6)-methyl-2-substituted Benzoxazole and Benzimidazole Derivatives. Arzneim.-Forsch. / Drug Res. 47(11), 1393 (1997)
16. Temiz, Ö., Ören, İ., Yalçin, İ. et al., Synthesis and microbiological activity of some novel 5- or 6-methyl-2-(2,4-disubstitutedphenyl)benzoxazole derivatives. Il Farmaco 53, 337 (1998)
17. Sener, E., Yalçin, İ., Özden, et al., 2-(p-Sübstitüefenil)-benzoksazol türevlerinin sentez, ve yapi aydinlatmasi ve mikrobiyolojik etkileri-I. FABAD. J. Pharm. Sci. 11, 190 (1986)
18. Şener, E., Yalçin, İ., Akin, A. et al., Antifungal activity of 2-benzylbenzoxazole derivatives and QSAR's by Free-Wilson Analysis. Gazi Ecz. Fak. Der. 4, 1 (1987)
19. Özden, T., Özden, S., Şener, E. et al., 5-Nitro-2-(p-sübstitüefenil)benzoksazol türevlerinin sentez ve yapi açiklamalari ve mikrobiyolojik etkileri-III. Farm. Bil. Der. 12, 39 (1987)
20. Yalçin, İ., Şener, E., Özden, T., 2-(P-Sübstitüefenil)oksazolo(4,5-b)piridin türevlerinin sentez ve yapi açiklamalan. Ank. Ecz. Fak. Der. 15, 69 (1985)
21. Şener, E. A., Arpaci-Temiz, Ö., Yalçin, İ. et al., Synthesis and microbiological activity of some novel 5-benzamido- and 5-phenylacetamido- substituted 2-phenylbenzoxazole derivatives. Il Farmaco, 55, 397 (2000)
22. Aizpurua, J. M., Palomo, C., Reagents and synthetic methods, improved synthesis of 2-substituted benzoxazoles induced by trimethylsilyl polyphosphate (PPSE). Soc. Chim. France Bull. 27, 142 (1984)
23. Phillips, M. A., The formation of 2-substituted benzimidazoles. J. Chem. Soc. 2393 (1928)