Structure-activity relationship study of pyrimido[1,2-c][1,3]benzothiazin- 6-imine derivatives for potent anti-HIV agents

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 21, 2012, Pages 6434-6441

  Mizuhara, Tsukasa ^a   Oishi, Shinya ^a   Ohno, Hiroaki ^a   Shimura, Kazuya ^a   Matsuoka, Masao ^a   Fujii, Nobutaka ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Anti HIV agents; PD 404182; Pyrimidobenzothiazine

Indexed keywords

1 (4 METHOXYBENZYL)PIPERIDINE 4,4 DICARBONITRILE; 3 (4 BROMO 2 FLUOROPHENYL) 9 (4 METHOXYBENZYL) 2,4,9 TRIAZASPIRO[5.5]UNDEC 2 ENE; 3,4 DIHYDRO 2H,6H PYRIMIDO[1,2 C][1,3]BENZOTHIAZIN 6 IMINE; 3,4 DIHYDRO 9 (4 METHOXYCARBONYLPHENYL) 2H,6H PYRIMIDO[1,2 C][1,3]BENZOTHIAZIN 6 IMINE; 9 BROMO N (TERT BUTYL) 1' (4 METHOXYBENZYL) 2H SPIRO[BENZO[E]PYRIMIDO[1,2 C][1,3]THIAZINE 3,4' PIPERIDIN] 6(4H)IMINE; 9 BROMO N (TERT BUTYL) 1' (METHANESULFONYL) 2H SPIRO[BENZO[E]PYRIMIDO[1,2 C][1,3]THIAZINE 3,4' PIPERIDIN] 6(4H)IMINE; 9 BROMO N (TERT BUTYL) 1' (METHOXYCARBONYL) 2H SPIRO[BENZO[E]PYRIMIDO[1,2 C][1,3]THIAZINE 3,4' PIPERIDIN] 6(4H)IMINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; BIS(2 CHLOROETHYL) N (4 METHOXYBENZYL)AMINE; DEXTRAN SULFATE; ENFUVIRTIDE; N (TERT BUTYL) 3,4 DIHYDRO 9 (1H PYRAZOL 1 YL) 2H,6H PYRIMIDO[1,2 C][1,3]BENZOTHIAZIN 6 IMINE; N (TERT BUTYL) 3,4 DIHYDRO 9 (4 METHOXYCARBONYLPHENYL) 2H,6H PYRIMIDO[1,2 C][1,3]BENZOTHIAZIN 6 IMINE; NEVIRAPINE; PD 404182; RALTEGRAVIR; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ANTIVIRAL SUSCEPTIBILITY; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG DESIGN; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; HELA CELL; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; INCUBATION TIME; NONHUMAN; PHYSICAL CHEMISTRY; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SUZUKI MIYAURA REACTION; ULLMANN COUPLING REACTION; VIRUS STRAIN;

ANTI-HIV AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; HELA CELLS; HIV-1; HUMANS; IMINES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN ECHOVIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2;

EID: 84867576677     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.08.030     Document Type: Article

References (45)

1. M.A. Thompson, J.A. Aberg, P. Cahn, J.S.G. Montaner, G. Rizzardini, A. Telenti, J.M. Gatell, H.F. Günthard, S.M. Hammer, M.S. Hirsch, D.M. Jacobsen, P. Reiss, D.D. Richman, P.A. Volberding, P. Yeni, and R.T. Schooley J. Am. Med. Assoc. 304 2010 321
2. R.C. Rathbun, S.M. Lockhart, and J.R. Stephens Curr. Pharm. Des. 12 2006 1045
3. V.A. Johnson, V. Calvez, H.F. Günthard, R. Paredes, D. Pillay, R. Shafer, A.M. Weinsing, and D.D. Richman Top. Antiviral Med. 19 2011 156
4. A. Carr, and D.A. Cooper Lancet 356 2000 1423
5. J.M. Kilby, and J.J. Eron N. Engl. J. Med. 348 2003 2228
6. J.P. Lalezari, K. Henry, M. O'Hearn, J.S. Montaner, P.J. Piliero, B. Trottier, S. Walmsley, C. Cohen, D.R. Kuritzkes, J.J. Eron Jr., J. Chung, R. DeMasi, L. Donatacci, C. Drobnes, J. Delehanty, and M. Salgo N. Engl. J. Med. 348 2003 2175
7. T. Matthews, M. Salgo, M. Greenberg, J. Chung, R. DeMasi, and D. Bolognesi Nat. Rev. Drug Disc. 3 2004 215
8. B. Grinsztejn, B.-Y. Nguyen, C. Katlama, J.M. Gatell, A. Lazzarin, D. Vittecoq, C.J. Gonzalez, J. Chen, C.M. Harvey, and R.D. Isaacs Lancet 369 2007 1261
9. R.T. Steigbigel, D.A. Cooper, P.N. Kumar, J.E. Eron, M. Schechter, M. Markowitz, M.R. Loutfy, J.L. Lennox, J.M. Gatell, J.K. Rockstroh, C. Katlama, P. Yeni, A. Lazzarin, B. Clotet, J. Zhao, J. Chen, D.M. Ryan, R.R. Rhodes, J.A. Killar, L.R. Gilde, K.M. Strohmaier, A.R. Meibohm, M.D. Miller, D.J. Hazuda, M.L. Nessly, M.J. DiNubile, R.D. Isaacs, B.-Y. Nguyen, and H. Teppler N. Engl. J. Med. 359 2008 339
10. P. Dorr, M. Westby, S. Dobbs, P. Griffin, B. Irvine, M. Macartney, J. Mori, G. Rickett, C. Smith-Burchnell, C. Napier, R. Webster, D. Armour, D. Price, B. Stammen, A. Wood, and M. Perros Antimicrob. Agents Chemother. 49 2005 4721
11. G. Fätkenheuer, A.L. Pozniak, M.A. Johnson, A. Plettenberg, S. Staszewski, A.I.M. Hoepelman, M.S. Saag, F.D. Goebel, J.K. Rockstroh, B.J. Dezube, T.M. Jenkins, C. Medhurst, J.F. Sullivan, C. Ridgway, S. Abel, I.T. James, M. Youle, and E. VanDerRyst Nat. Med. 11 2005 1170 1172
12. G.J. Bridger, R.T. Skerlj, D. Thornton, S. Padmanabhan, S.A. Martellucci, G.W. Henson, M.J. Abrams, N. Yamamoto, K. De Vreese, R. Pauwels, and E. De Clercq J. Med. Chem. 38 1995 366
13. G.J. Bridger, R.T. Skerlj, P.E. Hernandez-Abad, D.E. Bogucki, Z. Wang, Y. Zhou, S. Nan, E.M. Boehringer, T. Wilson, J. Crawford, M. Metz, S. Hatse, K. Princen, E. De Clercq, and D. Schols J. Med. Chem. 53 2010 1250
14. N. Fujii, S. Oishi, K. Hiramatsu, T. Araki, S. Ueda, H. Tamamura, A. Otaka, S. Kusano, S. Terakubo, H. Nakashima, J.A. Broach, J.O. Trent, Z.-X. Wang, and S.C. Peiper Angew. Chem., Int. Ed. 42 2003 3251
15. S. Ueda, S. Oishi, Z.-X. Wang, T. Araki, H. Tamamura, J. Cluzeau, H. Ohno, S. Kusano, H. Nakashima, J.O. Trent, S.C. Peiper, and N. Fujii J. Med. Chem. 50 2007 192
16. E. Inokuchi, S. Oishi, T. Kubo, H. Ohno, K. Shimura, M. Matsuoka, and N. Fujii ACS Med. Chem. Lett. 2 2011 477
17. Q. Zhao, L. Ma, S. Jiang, H. Lu, S. Liu, Y. He, N. Strick, N. Neamati, and A.K. Debnath Virology 339 2005 213
18. J.M. Lalonde, Y.D. Kwon, D.M. Jones, A.W. Sun, J.R. Courter, T. Soeta, T. Kobayashi, A.M. Princiotto, X. Wu, A. Schön, E. Freire, P.D. Kwong, J.R. Mascola, J. Sodroski, N. Madani, and A.B. Smith J. Med. Chem. 55 2012 4382
19. F. Curreli, S. Choudhury, I. Pyatkin, V.P. Zagorodnikov, A.K. Bulay, A. Altieri, Y.D. Kwon, P.D. Kwong, and A.K. Debnath J. Med. Chem. 55 2012 4764
20. T. Wang, Z. Yin, Z. Zhang, J.A. Bender, Z. Yang, G. Johnson, Z. Yang, L.M. Zadjura, C.J. D'Arienzo, D.D. Parker, C. Gesenberg, G.A. Yamanaka, Y.-F. Gong, H.-T. Ho, H. Fang, N. Zhou, B.V. McAuliffe, B.J. Eggers, L. Fan, B. Nowicka-Sans, I.B. Dicker, Q. Gao, R.J. Colonno, P.-F. Lin, N.A. Meanwell, and J.F. Kadow J. Med. Chem. 52 2009 7778
21. A. Otaka, M. Nakamura, D. Nameki, E. Kodama, S. Uchiyama, S. Nakamura, H. Nakano, H. Tamamura, Y. Kobayashi, M. Matsuoka, and N. Fujii Angew. Chem., Int. Ed. 41 2002 2938
22. S. Oishi, S. Ito, H. Nishikawa, K. Watanabe, M. Tanaka, H. Ohno, K. Izumi, Y. Sakagami, E. Kodama, M. Matsuoka, and N. Fujii J. Med. Chem. 51 2008 388
23. S. Oishi, K. Watanabe, S. Ito, M. Tanaka, H. Nishikawa, H. Ohno, K. Shimane, K. Izumi, Y. Sakagami, E.N. Kodama, M. Matsuoka, A. Asai, and N. Fujii Med. Chem. Commun. 1 2010 276
24. A.R. Katritzky, S.R. Tala, H. Lu, A.V. Vakulenko, Q.-Y. Chen, J. Sivapackiam, K. Pandya, S. Jiang, and A.K. Debnath J. Med. Chem. 52 2009 7631
25. S. Jiang, S.R. Tala, H. Lu, N.E. Abo-Dya, I. Avan, K. Gyanda, L. Lu, A.R. Katritzky, and A.K. Debnath J. Med. Chem. 54 2011 572
26. G. Zhou, D. Wu, B. Snyder, R.G. Ptak, H. Kaur, and M. Gochin J. Med. Chem. 54 2011 7220
27. M.R. Birck, T.P. Holler, and R.W. Woodard J. Am. Chem. Soc. 122 2000 9334
28. B.P. Duckworth, and C.C. Aldrich Anal. Biochem. 403 2010 13
29. T.L. Foley, A. Yasgar, C.J. Garcia, A. Jadhav, A. Simeonov, and M.D. Burkart Org. Biomol. Chem. 8 2010 4601
30. K. Watanabe, S. Negi, Y. Sugiura, A. Kiriyama, A. Honbo, K. Iga, E.N. Kodama, T. Naitoh, M. Matsuoka, and K. Kano Chem. Asian J. 5 2010 825
31. M. Baba, D. Scgols, R. Pauwels, H. Nakashima, and E. De Clercq J. Acquir. Immune. Defic. Syndr. 3 1990 493
32. K. Chockalingam, R.L. Simeon, C.M. Rice, and Z. Chen Proc. Natl. Acad. Sci. U.S.A. 107 2010 3764
33. A.M. Chamoun, K. Chockalingam, M. Bobardt, R. Simeon, J. Chang, P. Gallay, and Z. Chen Antimicrob. Agents Chemother. 56 2012 672
34. T. Mizuhara, S. Oishi, H. Ohno, K. Shimura, M. Matsuoka, and N. Fujii Org. Biomol. Chem. 10 2012 6792
35. T. Mizuhara, S. Inuki, S. Oishi, N. Fujii, and H. Ohno Chem. Commun. 2009 3413
36. T. Mizuhara, S. Oishi, N. Fujii, and H. Ohno J. Org. Chem. 75 2010 265
37. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
38. A. Suzuki J. Organomet. Chem. 576 1999 147
39. A. Mitschb, M. Altenkämpera, I. Sattlerc, and M. Schlitzer Arch. Pharm. Chem. Life Sci. 338 2005 9
40. K. Kunz, U. Scholz, and D. Ganzer Synlett 2003 2428
41. M. Ishihara, and H. Togo Tetrahedron 63 2007 1474
42. M.A. Fischl, D.D. Richman, and M.H. Grieco N. Engl. J. Med. 317 1987 185
43. V.J. Merluzzi, K.D. Hargrave, M. Labadia, K. Grozinger, M. Skoog, J.C. Wu, C.-K. Shih, K. Eckner, S. Hattox, J. Adams, A.S. Rosehthal, R. Faanes, R.J. Eckner, R.A. Koup, and J.L. Sullivan Science 250 1990 1411
44. M. Skoog, K.D. Hargrave, J.J. Miglietta, E.B. Kopp, and V.J. Merluzzi Med. Res. Rev. 12 1992 27
45. M. Witvrouw, C. Pannecouque, W.M. Switzer, T.M. Folks, E. De Clercq, and W. Heneine Antiviral Ther. 9 2004 57