Synthesis of 2-(aminocarbonylmethylthio)-1H-imidazoles as novel Capravirine analogues

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 13, 2005, Pages 4209-4220

  Loksha, Yasser M ^a   El Barbary, Ahmed A ^b   El Badawi, Mahmoud A ^b   Nielsen, Claus ^c   Pedersen, Erik B ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^b Tanta University   (Egypt)

^c STATENS SERUM INSTITUT   (Denmark)

Author keywords

Aminoketones; Human imminodeficiency virus; Imidazole 2 thiones; Non nucleoside reverse transcriptase inhibitors

Indexed keywords

2 [1 (BENZYLOXYMETHYL) 5 (3,5 DIMETHYLBENZYL) 4 ETHYL 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [1 (BENZYLOXYMETHYL) 5 (3,5 DIMETHYLBENZYL) 4 ISOPROPYL 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [1 (BENZYLOXYMETHYL) 5 (CYCLOHEXYLMETHYL) 4 ISOPROPYL 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [4 (3,5 DIMETHYLBENZYL) 5 ETHYL 1 (PYRIDIN 4 YLMETHYL) 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [4 (CYCLOHEXYLMETHYL) 5 ETHYL 1 (PYRIDIN 4 YLMETHYL) 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [5 (3,5 DIMETHYLBENZYL) 1 (ETHOXYMETHYL) 4 ETHYL 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [5 (3,5 DIMETHYLBENZYL) 1 (ETHOXYMETHYL) 4 ISOPROPYL 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [5 (3,5 DIMETHYLBENZYL) 4 ETHYL 1 (PYRIDIN 4 YLMETHYL) 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [5 (3,5 DIMETHYLBENZYL) 4 ISOPROPYL 1 (PYRIDIN 4 YLMETHYL) 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [5 (CYCLOHEXYLMETHYL) 1 (ETHOXYMETHYL) 4 ETHYL 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [5 (CYCLOHEXYLMETHYL) 1 (ETHOXYMETHYL) 4 ISOPROPYL 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [5 (CYCLOHEXYLMETHYL) 4 ETHYL 1 (PYRIDIN 4 YLMETHYL) 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [5 (CYCLOHEXYLMETHYL) 4 ISOPROPYL 1 (PYRIDIN 4 YLMETHYL) 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [5 BENZYL 1 (ETHOXYMETHYL) 4 ISOPROPYL 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 [5 BENZYL 4 ISOPROPYL 1 (PYRIDIN 4 YLMETHYL) 1H IMIDAZOL 2 YLTHIO]ACETAMIDE; 2 AMINO 1 (3,5 DIMETHYLPHENYL) 4 METHYLPENTAN 3 ONE; 4 (3,5 DIMETHYLBENZYL) 5 ETHYL 1,3 DIHYDROIMIDAZOLE 2 THIONE; 4 (3,5 DIMETHYLBENZYL) 5 ISOPROPYL 1,3 DIHYDROIMIDAZOLE 2 THIONE; 5 BENZYL 1 ETHYL 4 ISOPROPYL 1,3 DIHYDROIMIDAZOLE 2 THIONE; ACETAMIDE DERIVATIVE; ACETIC ACID DERIVATIVE; CHLORIDE; CHLOROACETIC ACID; EMIVIRINE; IMIDAZOLE DERIVATIVE; IODOACETAMIDE; PYRIDINE DERIVATIVE; THIOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; DAKIN WEST REACTION; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROLYSIS; NONHUMAN; POLYMERIZATION;

ANTI-HIV AGENTS; CELL LINE; HIV-1; HUMANS; IMIDAZOLES; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR COMPOUNDS; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 20344382272     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.04.024     Document Type: Article

References (30)

1. E. De Clercq Antiviral Res. 38 1998 153
2. L.A. Kohlstaedt, J. Wang, J.M. Friedman, P.A. Rice, and T.A. Steitz Science 256 1992 1783
3. J. Ren, R. Esnouf, E. Garman, D. Somers, C. Ross, I. Kirby, J. Keeling, G. Darby, Y. Jones, D. Stuart, and D. Stammers Nature Struct. Biol. 2 1995 293
4. J. Ding, K. Das, C. Tantillo, W. Zhang, A.D.J. Clark, S. Jessen, X. Lu, Y. Hsiou, A. Jacobo-Molina, K. Andries, R. Pauwels, H. Moereels, L. Koymans, P.A.J. Janssen, R.H.J. Smith, R. Kroeger Koepke, C.J. Michejda, S.H. Hughes, and E. Arnold Structure 3 1995 365
5. R. Esnouf, J. Ren, C. Ross, Y. Jones, D. Stammers, and D. Stuart Nature Struct. Biol. 2 1995 303
6. D. Richman, C.-K. Shih, I. Lowy, J. Rose, P. Prodanovich, S. Goff, and J. Griffin Proc. Natl. Acad. Sci. U.S.A. 88 1991 11241
7. D.D. Richman, D. Havlir, J. Corbeil, D. Looney, C. Ignacio, S.A. Spector, J. Sullivan, S. Cheeseman, K. Barringer, D. Pauletti, C.-K. Shih, M. Myers, and J. Griffin J. Virol. 68 1994 1660
8. B.A. Larder J. Gen. Virol. 75 1994 951
9. R.F. Schinazi, B.A. Larder, and J.W. Mellors Int. Antiviral News 5 1997 129
10. J. Ren, R. Esnouf, A. Hopkins, C. Ross, Y. Jones, D. Stammers, and D. Stuart Structure 3 1995 915
11. A.L. Hopkins, J. Ren, R.M. Esnouf, B.E. Willcox, E.Y. Jones, C. Ross, T. Miyasaka, R.T. Walker, H. Tanaka, D.K. Stammers, and D.I. Stuart J. Med. Chem. 39 1996 1589
12. G. Maga, M. Amacker, N. Ruel, U. Hubscher, and S. Spadari J. Mol. Biol. 274 1997 738
13. J. Ren, C. Nichols, L.E. Bird, T. Fujiwara, H. Sugimoto, D.I. Stuart, and D.K. Stammers J. Biol. Chem. 275 2000 14316
14. T. Fujiwara, A. Sato, M. El-Farrash, S. Miki, K. Abe, Y. Isaka, M. Kodama, Y. Wu, B.L. Chen, H. Harada, H. Sugimoto, M. Hatanaka, and Y. Hinuma Antimicrob. Agents Chemother. 42 1998 1340
15. From AIDsmeds.com's home page: http://www.aidsmeds.com/drugs/capravirine. htm
16. H.D. Dakin, and R. West J. Biol. Chem. 78 1928 91
17. H.D. Dakin, and R. West J. Biol. Chem. 78 1928 745
18. R.R. Herr, T. Enkoji, and J.P. Dailey J. Org. Chem. 79 1957 4229
19. G.H. Cleland, and C. Niemann J. Am. Chem. Soc. 71 1949 841
20. Y.M. Loksha, P.T. Jørgensen, E.B. Pedersen, M.A. El-Badawi, A.A. El-Barbary, and C. Nielsen J. Heterocycl. Chem. 39 2002 375
21. G.S. Sheppard, A.S. Florjancic, J.R. Giesler, L. Xu, Y. Guo, S.K. Davidsen, P.A. Marcotte, I. Elmore, D.H. Albert, T.J. Magoc, J.J. Bouska, C.L. Goodfellow, D.W. Morgan, and J.B. Summers Bioorg. Med. Chem. Lett. 8 1998 3251
22. R.A.F. Bullerwell, and A. Lawson J. Chem. Soc. 1952 1350
23. Y.M. Loksha, M.A. El-Badawi, A.A. El-Barbary, E.B. Pedersen, and C. Nielsen Arch. Pharm. 336 2003 175
24. H. Tanaka, H. Takashima, M. Ubasawa, K. Sekiya, N. Inouye, M. Baba, S. Shigeta, R.T. Walker, E. De Clerq, and T. Miyasaka J. Med. Chem. 38 1995 2860
25. A.L. Hopkins, J. Ren, H. Tanaka, M. Baba, M. Okamato, D.I. Stuart, and D.K. Stammers J. Med. Chem. 42 1999 4500
26. R. Vig, C. Mao, T.K. Venkatachalam, L. Tuel-Ahlgren, E.A. Sudbeck, and F.M. Uckun Bioorg. Med. Chem. Lett. 8 1998 1461
27. M. Popovic, M.G. Sarngadharan, E. Read, and R.C. Gallo Science 224 1984 497
28. S. Harada, Y. Koyanagi, and N. Yamamoto Science 229 1985 563
29. T. Mosmann J. Immunol. Methods 63 1983 55
30. R. Ling, M. Yoshida, and P.S. Mariano J. Org. Chem. 61 1996 4439