Anti-AIDS Agents. 52. Synthesis and Anti-HIV Activity of Hydroxymethyl (3′R,4′R)-3′,4′-Di-O-(S)-camphanoyl-(+)-cis-khellactone Derivatives

Journal of Medicinal Chemistry

Volumn 47, Issue 3, 2004, Pages 756-760

  Xie, Lan ^a   Yu, Donglei ^a   Wild, Carl ^b   Allaway, Graham ^b   Turpin, Jim ^c   Smith, Philip C ^a   Lee, Kuo Hsiung ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b Panacos Pharmaceuticals   (United States)

^c TherImmune Research Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 BROMOMETHYL 4 METHYL 3',4' DI O CMPHANOYLKHELLACTONE; 3 HYDROXYMETHYL 3',4' DI O CAMPHANOYLKHELLACTONE; 4 METHYL 3',4' DI O CAMPHANOYLKHELLACTONE; ANTIRETROVIRUS AGENT; CARBOXYMETHYLCELLULOSE; COUMARIN; DOUBLE STRANDED DNA; KHELLACTONE; NEVIRAPINE; SINGLE STRANDED DNA; UNCLASSIFIED DRUG; VIRUS DNA; WATER; ZIDOVUDINE;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ANIMAL EXPERIMENT; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG FORMULATION; DRUG HALF LIFE; DRUG MECHANISM; DRUG POTENCY; DRUG SOLUBILITY; DRUG STRUCTURE; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS; MALE; NONHUMAN; PERIPHERAL BLOOD MONONUCLEAR CELL; RAT;

ANIMALS; ANTI-HIV AGENTS; BIOLOGICAL AVAILABILITY; CAMPHOR; CELL LINE; HIV-1; HUMANS; LACTONES; RATS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

EID: 1642499653     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030416y     Document Type: Article

References (12)

1. Gottlieb, M. S.; Schroff, R.; Schanker, H. M.; Weisman, J. D.; Fan, P. T.; Wolf, R. A.; Saxon, A. Pneumocystis Carinii Pneumonia and Mucosal Candidiasis in Previously Healthy Homosexual Men. N. Engl. J. Med. 1981, 305, 1425-1431.
2. Barre-Sinoussi, F.; Chermann, J. C.; Rey, F.; Nugeyre, M. T.; Chamaret, S.; Gruest, J.; Dauguet, C.; Axler-Blin, C.; Vezinet-Brun, F.; Rouzioux, C.; Rozenbaum, W.; Montagnier, L. Isolation of a T-Lymphotropic Retrovirus from a Patient at Risk for Acquired Immune Deficiency Syndrome (AIDS). Science 1983, 220, 868-871.
3. UNAIDS and WHO. AIDS Epidemic Update. Trop. Doc. 2001, 32, 189.
4. Huang, L.; Kashiwada, Y.; Cosentino, L. M.; Fan, S.; Lee, K. H. 3′,4′-Di-O-(-)-Camphanoyl-(+)-cis-Khellactone and Related Compounds: A New Class of Potent Anti-HIV Agents. Bioorg. Med. Chem. Lett. 1994, 4, 593-598.
5. Huang, L.; Kashiwada, Y.; Cosentino, L. M.; Fan, S.; Chen, C. H.; McPhail, A. T.; Fujioka, T.; Mihashi, K.; Lee, K. H. Anti-AIDS Agents. 15. Synthesis and Anti-HIV Activity of Dihydroseselins and Related Analogues. J. Med. Chem. 1994, 37, 3947-3955.
6. Xie, L.; Takeuchi, Y.; Cosentino, L. M.; McPhail, A. T.; Lee, K. H. Anti-AIDS Agents. 42. Synthesis and Anti-HIV Activity of Disubstituted (3′R,4′R)-3′,4′-di-O-(S)-Camphanoyl-(+)-cis-Khellactone Analogues. J. Med. Chem. 2001, 44, 664-671.
7. Xie, L.; Takeuchi, Y.; Cosentino, L. M.; Lee, K. H. Anti-AIDS Agents. 37. Synthesis and Structure-Activity Relationships of (3′R,4′ R)-(+)-cis-Khellactone Derivatives as Novel Potent Anti-HIV Agents. J. Med. Chem. 1999, 42, 2662-2672.
8. Xie, L.; Takeuchi, Y.; Cosentino, L. M.; Lee, K. H. Anti-AIDS Agents 33 Synthesis and Anti-HIV Activity of Monomethyl Substituted 3′,4′ -di-O-(-)-Camphanoyl-(+)-cis-Khellactone (DCK) Analogues. Bioorg. Med. Chem. Lett. 1998, 8, 2151-2156.
9. Takeuchi, Y.; Xie, L.; Cosentino, L. M.; Lee, K. H. Anti-AIDS agents-XXVIII. Synthesis and Anti-HIV Activity of Methoxy Substituted 3′,4′-di-O-(-)-Camphanoyl-(+)-cis-Khellactone (DCK) Analogues. Bioorg. Med. Chem. Lett. 1997, 7, 2573-2578.
10. Yu, D.; Suzuki, M.; Xie, L.; Morris-Natschke, S. L.; Lee, K. H. Recent Progress in the Development of Coumarin Derivatives as Potent Anti-HIV Agents. Med. Res. Rev. 2003, 23, 322-345.
11. Xie, L.; Allaway, G.; Wild, C.; Kilgore, N.; Lee, K. H. Anti-AIDS Agents Part 47. Synthesis and Anti-HIV Activity of 3-Substituted 3′,4′ -di-O-(S)-Camphanoyl-(3′R,4′R)-(+)-cis-Khellactone Derivatives. Bioorg. Med. Chem. Lett. 2001, 11, 2291-2293.
12. Chilin, A.; Marzano, C.; Guiotto, A.; Manzini, P.; Baccichetti, F.; Carlassare, F.; Bordin, F. Synthesis and Biological Activity of (Hydroxymethyl)- and (Diethylaminomethyl)benzopsoralens. J. Med. Chem. 1999, 42, 2936-2945.