Anti-AIDS agents 84. Synthesis and anti-human immunodeficiency virus (HIV) activity of 2′-monomethyl-4-methyl- and 1′-thia-4-methyl-(3′R, 4′R)-3′,4′-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) analogs

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 20, 2010, Pages 7203-7211

  Xu, Shi Qing ^a   Yan, Xin ^a   Chen, Ying ^a   Xia, Peng ^a   Qian, Keduo ^b   Yu, Donglei ^b   Xia, Yi ^b   Yang, Zheng Yu ^b   Morris Natschke, Susan L ^b   Lee, Kuo Hsiung ^b,c  

^a FUDAN UNIVERSITY   (China)

^b University of North Carolina   (United States)

^c CHINA MEDICAL UNIVERSITY   (Taiwan)

Author keywords

1 Thia 4 methyl (3 R,4 R) 3 ,4 di O (S) camphanoyl (+) cis khellactone (DCK) analogs; 2 Monomethyl 4 methyl (3 R,4 R) 3 , 4 di O (S) camphanoyl (+) cis khellactone (DCK) analogs

Indexed keywords

1 SULFONE 2',4 DIMETHYL 3',4' DI O CAMPHANOYL KHELLACTONE; 1 SULFOXIDE 2',4 DIMETHYL 3',4' DI O CAMPHANOYL KHELLACTONE; 1 THIA 2',4 DIMETHYL 3',4' DI O CAMPHANOYL KHELLACTONE; 2',4 DIMETHYL 3',4' DI O CAMPHANOYL KHELLACTONE; KHELLACTONE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; LYMPHOCYTE; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; VIRUS REPLICATION;

ACQUIRED IMMUNODEFICIENCY SYNDROME; ANTI-HIV AGENTS; CAMPHOR; CRYSTALLOGRAPHY, X-RAY; DNA REPLICATION; DRUG DESIGN; HIV-1; HUMANS; LACTONES; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; THIA;

EID: 77957581403     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.08.031     Document Type: Article

References (22)

1. M.S. Gottlieb, R. Schroff, H.M. Schanker, J.D. Weisman, P.T. Fan, R.A. Wolf, and A.N. Saxon Engl. J. Med. 305 1981 1425
2. F. Barre-Sinoussi, J.C. Chermann, F. Rey, M.T. Nugeyre, S. Chamaret, J. Gruest, C. Dauguet, C. Axler-Blin, F. Vezinet-Brun, C. Rouzioux, W. Rozenbaum, and L. Montagnier Science 220 1983 868
3. L. Huang, Y. Kashiwada, L.M. Cosentino, S. Fan, C.H. Chen, A.T. McPhail, T. Fujioka, K. Mihashi, and K.H. Lee J. Med. Chem. 37 1994 3947
4. D. Yu, M. Suzuki, L. Xie, S.L. Morris-Natschke, and K.H. Lee Med. Res. Rev. 23 2003 322
5. D. Yu, S.L. Morris-Natschke, and K.H. Lee Med. Res. Rev. 27 2007 108
6. L. Xie, H.F. Guo, H. Lu, X.M. Zhuang, A.M. Zhang, G. Wu, J.X. Ruan, T. Zhou, D. Yu, X. Qian, K.H. Lee, and S. Jiang J. Med. Chem. 25 2008 7689
7. J. Tang, K. Qian, B.N. Zhang, Y. Chen, P. Xia, D. Yu, Y. Xia, Z.Y. Yang, C.H. Chen, S.L. Morris-Natschke, and K.H. Lee Bioorg. Med. Chem. 18 2010 4363
8. L. Xie, Y. Takeuchi, L.M. Cosentino, and K.H. Lee J. Med. Chem. 42 1999 2662
9. L. Huang, X. Yuan, D. Yu, K.H. Lee, and C.H. Chen Virology 332 2005 623
10. L. Xie, D. Yu, C. Wild, G. Allaway, J. Turpin, P.C. Smith, and K.H. Lee J. Med. Chem. 47 2004 756
11. Q. Zhang, Y. Chen, P. Xia, Y. Xia, Z.Y. Yang, D.L. Yu, S.L. Morris-Natschke, and K.H. Lee Bioorg. Med. Chem. Lett. 14 2004 5855
12. Y. Chen, Q. Zhang, B.N. Zhang, P. Xia, Y. Xia, Z.Y. Yang, N. Kilgore, C. Wild, S.L. Morris-Natschke, and K.H. Lee Bioorg. Med. Chem. 12 2004 6383
13. T.L. Jacobs, W.L. Petty, and E.G. Teach J. Am. Chem. Soc. 82 1960 4094
14. K.B. Sharpless, W. Amberg, and Y.L. Bennani J. Org. Chem. 57 1992 2768
15. W.S. Zhou, L.F. Huang, L.Q. Sun, and X.F. Pan Tetrahedron Lett. 32 1991 6745
16. S. Takatsuto, and N. Ikekawa Chem. Pharm. Bull. 32 1984 2001
17. T.C. McMorris, and P.A. Patil J. Org. Chem. 58 1993 2338
18. G.A. Crispino, and K.B. Sharpless Synthesis 8 1993 777
19. H.C. Kolb, M.S. VanNieuwenhze, and K.B. Sharpless Chem. Rev. 94 1994 2483
20. P. Sebok, T. Timar, T. Eszenyi, and T. Patonay J. Org. Chem. 59 1995 6318
21. M. Tanaka, T. Kai, X.L. Sun, H. Takayanagi, T. Uda, and K. Furuhata Chem. Pharm. Bull. 43 1995 1844
22. C.D. Gabbutt, J.D. Hepworth, and B.M. Heron Tetrahedron 51 1995 13277