Design, synthesis and biological evaluation of a series of thioamides as non-nucleoside reverse transcriptase inhibitors

Medicinal Chemistry

Volumn 3, Issue 6, 2007, Pages 513-519

  Mehanna, Ahmed S ^a   Belani, Jitendra D ^b   Kelley, Charles J ^a   Pallansch, Luke A ^c,d  

^a MASSACHUSETTS COLLEGE OF PHARMACY AND HEALTH SCIENCES   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

^c SOUTHERN RESEARCH INSTITUTE   (United States)

^d Assay and Product Development   (United States)

Author keywords

Non nucleoside reverse transcriptase inhibitors; PETT bio isosteres; Thioamides

Indexed keywords

LY 73497; N (2 CHLOROBENZYL) 2 PYRIDIN 2 YLTHIOACETAMIDE; N (2 PHENETHYL) 2 PYRIDIN 2 YLETHIOETHANAMIDE; N (4 CHLOROPHENYL) 2 PYRIDIN 2 YLTHIOETHANAMIDE; N (5 CHLOROPYRIDIN 2 YL) 2 (2,6 DIFLUOROPHENYL)THIOACETAMIDE; N (5 CHLOROPYRIDIN 2 YL) 3 PHENYLTHIOPROPANAMIDE; N (5 CHLOROPYRIDIN 2 YL) 4 PHENYLTHIOBUTANAMIDE; N (5 CHLOROPYRIDIN 2 YL) 4 PHENYLTHIOPROPANAMIDE; N (PYRIDIN 2 YLMETHYL) 2 (2,6 DIFLUOROPHENYL)THIOACETAMIDE; N [(2 PYRIDIN 2 YL)ETHYL] 2 (2,6 DIFLUOROPHENYL)THIOACETAMIDE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; THIOAMIDE; TROVIRDINE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DESIGN; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; NONHUMAN; PRIORITY JOURNAL; VIRUS CULTURE; VIRUS RESISTANCE; VIRUS STRAIN; WILD TYPE;

ANTI-HIV AGENTS; DRUG DESIGN; HIV REVERSE TRANSCRIPTASE; INHIBITORY CONCENTRATION 50; MUTATION; PYRIDINES; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; THIOAMIDES;

EID: 37349000576     PISSN: 15734064     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340607782360344     Document Type: Article

References (24)

1. Waters, L.; John, L.; Nelson, M. Intern. J. Clin. Pract., 2007, 61(1), 105-118.
2. Boone, L.R. Curr. Opin. Investig. Drugs, 2006, 7(2), 128-135.
3. Fortin, C.; Joly, V.; Yeni, P. Ex. Opin. Emerg. Drugs, 2006, 11(2), 217-230.
4. Douali, L.; Cherqaoui, D. Curr. Comput. Aided Drug Des., 2006, 2(1), 21-29.
5. Ahgren, C.; Backro, K.; Bell, F. W.; Cantrell, A. S.; Clemens, M.; Colacino, J. M.; Deeter, J. B.; Engelhardt J. A.; Hogberg, M.; Jaskunas, S. R.; Johansson, N. G.; Jordan, C. L.; Kasher, J. S.; Kinnick, M. D.; Lind, P.; Lopez, C.; Morin, Jr., J. M.; Muesing, M. A.; Noreen, R.; Oberg, B.; Paget, C. J.; Palkowitz, J. A.; Parrish, C. A.; Pranc, P.; Rippy, M. K; Rydergard, C.; Sahlberg, C.; Swanson, S.; Temansky, R. J.; Unge, T.; Vasileff, R. T.; Vrang, L.; West, S. J.; Zhang, H.; Zhou, X. X. Antimicrob, Agents Chemother., 1995, 39, 13211.
6. Spence, R. A.; Kati, W. M.; Anderson, K.; Johnson, J. A. Science, 1995, 267, 988.
7. Bell, F. W.; Cantrell, A. S.; Hogberg, M.; Jaskunas, S.R.; Johansson, N. G.; Jordan, C. L.; Kinnick, M. D.; Lind, P.; Morin, J. M.; Noreen, FL; Öberg, B.; Palkowitz, J. A.; Parrish, C. A.; Pranc, P.; Sahlberg, C.; Ternansky, R. J.; Vasileff R. T.; Vrang, L.; West, S. J.; hang, H.; Zhou X. X. J. Med. Chem., 1995, 38, 4929.
8. Cantrell, A. S.; Engelhardt, P.; Högberg, M.; Jaskunas, S. R.; Johansson, N. G.; Jordan, C. L.; Kaugasmetsä J.; Kinnick, M. D.; Lind, P.; Morin, Jr., J. M.; Muesing, M. A.; Noréen, K; Öberg, B.; Pranc, P.; Sahlberg, C.; Ternansky, R. J.; Vasileff, R. T.; Vrang, L.; West, S. J.; Zhang, H. J. Med. Chem., 1996, 39, 4261.
9. Mao, C.; Vig, R.; Venkatachalam, T. K.; Sudbeck, E. A.; Uckun F. M. Bioorg. Med. Chem. Lett., 1998, 8, 2213.
10. Vig, R.; Mao, C.; Venkatachalam, T. K.; Tuel-Ahlgren, L.; Sudbeck, E. A.; Uckun; F. M. Bioorg. Med.Chem., 1998, 6,1789.
11. Högberg, M.; Sahlberg, C.; Engelhardt, P.; Noreen, R.; Kangasmetsa, J.; Johansson, N. G.; Oberg, B. Vrang, L.; Zhang, H.; Sahlberg, B.; Unge, T.; Lovgren, S.; Fridborg, K.; Backbro, K. J. Med. Chem., 1999, 42, 4150.
12. Sahlberg, C.; Noréen, R.; Engelhardt, P.; Hogberg, M.; Kangasmetsa, J.; Vrang, L.; Zhang, H. Bioorg. Med. Chem. Lett., 1998, 8, 1511.
13. Högberg, M.; Engelhardt, P.; Vrang, L.; Zhang, H. Bioorg. Med. Chem. Lett., 2000, 10, 265.
14. Balzarini, J. Biochem. Pharmacol., 1999, 58, 1.
15. Taylor, C. L.; Wilkins, G. L. Future Virol., 2007, 2(1), 11-21.
16. Yin, P. D.; Das, D.; Mitsuya, H. Cell. Mol. Life Sci., 2006, 63 (15), 1706-1724.
17. Huang, W.; Limoli, K.; Sartoris, M. M.; Petropoulos, C.; Whitcomb J. Antivir. Ther., 1999, 4(Suppl. 1), 50. Abstract 73.
18. Petropoulos, C.J.; Parkin, N. T.; Limoli, K. L.; Lie, Y. S.; Wrin, T.; Huang, W.; Tian, H.; Smith, D.; Winslow, G. A.; Capon, D. J.; Whitcomb, J. M. Antmicrob. Agents Chemother., 2000, 44, 920.
19. Demeter, L. M.; Shafer, R. W.; Meehan, P. M; Holden-Wiltse, J.; Fischl, M. A.; Freimuth, W. W.; Para, M. F.; Reichman, R. C. Antimicrob. Agents Chemother., 2000, 44, 794.
20. Casado, J. L.; Hertogs, K.; Ruiz, L.; Dronda, F.; Cauwenberge, A. V.; Arno, A.; Garcia-Arata, I; Bloor, S.; Bonjoch, A.; Blazquez, J.; Clotet, B.; Larder, B. AIDS, 2000, 14, Fl-7.
21. Boyer, P. L.; Ferris, A. L.; Hughes, S. H. J. Virol., 1992, 66, 1031.
22. Buckheit, KW.; Kinjerski, T. L. Jr.; Fliakas-Boltz, V.; Russell, J. D.; Stop, T. L.; Patlansch, L A.; Brouwer, W. G.; Dao, D. C.; Harrison, W. A.; Schultz, K J.; Bader, J. P.; Yang, S. S. Antimicrab. Agents Chemother., 1995, 39, 2718.
23. Zhang, H.; Vrang, L.; Backbro, K.; Lind, P.; Salhberg, C.; Ubge, T.; Oberg, B. Antiviral. Res., 1995, 28, 331.
24. D'Cruz, O. J.; Venkatachalam, T. K.; Mao, C.; Quzi, S.; Uckun, F.M. Biol Reprod., 2002, 67(6), 1959.