Anti-AIDS agents 69. Moronic acid and other triterpene derivatives as novel potent anti-HIV agents

Journal of Medicinal Chemistry

Volumn 49, Issue 18, 2006, Pages 5462-5469

  Yu, Donglei ^a   Sakurai, Yojiro ^a   Chen, Chin Ho ^b   Chang, Fang Rong ^c   Huang, Li ^b   Kashiwada, Yoshiki ^d   Lee, Kuo Hsiung ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b DUKE UNIVERSITY   (United States)

^c KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^d NIIGATA UNIVERSITY OF PHARMACY AND APPLIED LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 O (3,3 DIMETHYLSUCCINYL)BETULIC ACID; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; BETULIC ACID; GLYCYRRHETINIC ACID; GLYCYRRHIZIC ACID; MORONIC ACID; N [3BETA O (3',3' DIMETHYLSUCCINYL)OLEAN 18 EN 28 OYL](1 HYDROXYMETHYL 3 METHYL)BUTYLAMIDE; N [3BETA O (3',3' DIMETHYLSUCCINYL)OLEAN 18 EN 28 OYL]AMINOUNDECANOIC ACID; N [3BETA O (3',3' DIMETHYLSUCCINYL)OLEAN 18 EN 28 OYL]LEUCINE; OLEANOLIC ACID; PROTEINASE INHIBITOR; TRITERPENE; UNCLASSIFIED DRUG; URSOLIC ACID; ZIDOVUDINE;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; DRUG DESIGN; DRUG POTENCY; DRUG RESISTANCE; DRUG SYNTHESIS; HEPATITIS B; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; LYMPHOCYTE; NONHUMAN; STRUCTURE ACTIVITY RELATION; VIRUS INHIBITION; VIRUS REPLICATION; VIRUS RESISTANCE; VIRUS STRAIN;

ANTI-HIV AGENTS; CELL LINE; DRUG RESISTANCE, VIRAL; HIV PROTEASE INHIBITORS; HIV-1; HUMANS; LYMPHOCYTES; OLEANOLIC ACID; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33748539751     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0601912     Document Type: Article

References (17)

1. Nakagawa-Goto, K.; Lee, K. H. Anti-AIDS Agents 68. The first total synthesis of a unique potent anti-HIV chalcone from genus Desmos. Org. Lett. submitted for publication.
2. UNAIDS and WHO, AIDS epidemic update. 12-2005. http://www.unaids.org.
3. FDA, Antiretroviral drugs approved by FDA for HIV. http://www.fda.gov/ oashi/aids/virals.html.
4. Kashiwada, Y.; Hashimoto, F.; Cosentino, L. M.; Chen, C. H.; Garrett, P. E.; and Lee, K. H. Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents. J. Med. Chem. 1996, 39, 1016-1017.
5. Hashimoto, F.; Kashiwada, Y.; Cosentino, L. M.; Chen, C. H.; Garrett, P. E.; Lee, K. H. Anti-AIDS agents 27. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Bioorg. Med. Chem. 1997, 5, 2133-2143.
6. Li, F.; Goila-gaur, R.; Salzwedel, K.; Kilgore, N. R.; Reddick, M.; Matallana, C.; Castillo, A.; Zoumplis, D.; Martin, D. E.; Orenstein, J. M.; Allaway, G. P.; Freed, E. O.; Wild, C. T. PA-457: A potent HIV inhibitor that disrupts core condensation by targeting a late step in Gag processing. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 13555-13560.
7. Zhou, J.; Yuan, X.; Dismuke, D.; Forshey, B. M.; Lundquist, C.; Lee, K.-H.; Aiken, C.; Chen, C. H. Small-molecule inhibition of human immunodeficiency virus type 1 replication by specific targeting of the final step of virion maturation. J. Virol. 2004, 78, 922-929.
8. Sun, I. C.; Chen, C. H.; Kashiwada, Y.; Wu, J. H.; Wang, H. K.; Lee, K. H. anti-AIDS agents 49. Synthesis, anti-HIV, and anti-Fusion activities of IC9564 analogues based on betulinic acid. J. Med. Chem. 2002, 45, 4271-4275.
9. Holz-Smith, S. L.; Sun, I. C.; Jin, L.; Matthews, T. J.; Lee, K. H.; Chen, C. H. Role of human immunodeficiency virus (HIV) type 1 envelope in the anti-HIV activity of the betulinic acid derivative IC9564. Antimicrob. Agents Chemother. 2001, 45, 60-66.
10. Beatty, G.; Lalezari, J.; Eron, J.; Pollard, R.; Saag, M.; Doto, J.; Salzwedel, K.; Wild, C.; Allaway, G.; Jacobson, J.; Martin, D. Safety and antiviral activity of PA-457, the first-in-class maturation inhibitor, in a 10-day monotherapy study in HIV-1 infected patients. Presented at the 45th Conference on Antimicrobial Agents and Chemotherapy, Washington, DC, Dec 16-19, 2005.
11. Sun, I. C.; Wang, H. K.; Kashiwada, Y.; Shen, J. K.; Cosentino, L. M.; Chen, C. H.; Yang, L. M.; Lee, K. H. Anti-AIDS agents. 34. Synthesis and structure-activity relationships of betulin derivatives as anti-HIV agents. J. Med. Chem. 1998, 41, 4648-4657.
12. Kashiwada, Y.; Wang, H. K.; Nagao, T.; Kitanaka, S.; Yasuda, I.; Fujioka, T.; Yamagishi, T.; Cosentino, L. M.; Kozuka, M.; Okabe, H.; Ikeshiro, Y.; Hu, C. Q.; Yeh, E.; Lee, K. H. Anti-AIDS agents 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids. J. Nat. Prod. 1998, 61, 1090-1095.
13. Huang, L.; Yuan, X.; Aiken, C.; Chen, C. H. Bi-functional anti-HIV-1 small molecules with two novel mechanisms of action. Antimicrob. Agents Chemother. 2004, 48, 663-665.
14. Ito, J.; Chang, F. R.; Wang, H. K.; Park, Y. K.; Ikegaki, M.; Kilgore, N.; Lee, K. H. Anti-AIDS agents. 48. Anti-HIV activity of moronic acid derivatives and the new melliterone-related triterpenoid isolated from Brazilian propolis. J. Nat. Prod. 2001, 64, 1278-1281.
15. Baltina, L. A. Chemical modification of glycyrrhizic acid as a route to new bioactive compounds for medicine. Curr. Med. Chem. 2003, 10, 155-171.
16. Kashiwada, Y.; Nagao, T.; Hashimoto, A.; Ikeshiro, Y.; Okabe, H.; Cosentino, L. M.; Lee, K. H. Anti-AIDS agents 38. Anti-HIV activity of 3-O-acyl ursolic acid derivatives. J. Nat. Prod. 2001, 63, 1619-1622.
17. Condra, J. H.; Schleif, W. A.; Blahy, O. M.; Gabryelski, L. J.; Graham, D. J.; Quintero, J. C.; Rhodes, A.; Robbins, H. L.; Roth, E.; Shivaprakash, M.; Titus, D.; Yang, T.; Teppler, H.; Squires, K. E.; Deutsch, P. J.; Emini, E. A. In vivo emergence of HIV-1 variants resistant to multiple protease inhibitors. Nature 1995, 374, 569-571.