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Anti-AIDS agents 81. Design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors.

Publication ,  Journal Article
Qian, K; Kuo, R-Y; Chen, C-H; Huang, L; Morris-Natschke, SL; Lee, K-H
Published in: J Med Chem
April 22, 2010

In our continuing study of triterpene derivatives as potent anti-HIV agents, different C-3 conformationally restricted betulinic acid (BA, 1) derivatives were designed and synthesized in order to explore the conformational space of the C-3 pharmacophore. 3-O-Monomethylsuccinyl-betulinic acid (MSB) analogues were also designed to better understand the contribution of the C-3' dimethyl group of bevirimat (2), the first-in-class HIV maturation inhibitor, which is currently in phase IIb clinical trials. In addition, another triterpene skeleton, moronic acid (MA, 3), was also employed to study the influence of the backbone and the C-3 modification toward the anti-HIV activity of this compound class. This study enabled us to better understand the structure-activity relationships (SAR) of triterpene-derived anti-HIV agents and led to the design and synthesis of compound 12 (EC(50): 0.0006 microM), which displayed slightly better activity than 2 as a HIV-1 maturation inhibitor.

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Published In

J Med Chem

DOI

EISSN

1520-4804

Publication Date

April 22, 2010

Volume

53

Issue

8

Start / End Page

3133 / 3141

Location

United States

Related Subject Headings

  • Virus Replication
  • Virion
  • Triterpenes
  • Structure-Activity Relationship
  • Stereoisomerism
  • Pentacyclic Triterpenes
  • Oleanolic Acid
  • Mutation
  • Medicinal & Biomolecular Chemistry
  • HIV-1
 

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Qian, K., Kuo, R.-Y., Chen, C.-H., Huang, L., Morris-Natschke, S. L., & Lee, K.-H. (2010). Anti-AIDS agents 81. Design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors. J Med Chem, 53(8), 3133–3141. https://doi.org/10.1021/jm901782m
Qian, Keduo, Reen-Yun Kuo, Chin-Ho Chen, Li Huang, Susan L. Morris-Natschke, and Kuo-Hsiung Lee. “Anti-AIDS agents 81. Design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors.J Med Chem 53, no. 8 (April 22, 2010): 3133–41. https://doi.org/10.1021/jm901782m.
Qian, Keduo, et al. “Anti-AIDS agents 81. Design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors.J Med Chem, vol. 53, no. 8, Apr. 2010, pp. 3133–41. Pubmed, doi:10.1021/jm901782m.
Journal cover image

Published In

J Med Chem

DOI

EISSN

1520-4804

Publication Date

April 22, 2010

Volume

53

Issue

8

Start / End Page

3133 / 3141

Location

United States

Related Subject Headings

  • Virus Replication
  • Virion
  • Triterpenes
  • Structure-Activity Relationship
  • Stereoisomerism
  • Pentacyclic Triterpenes
  • Oleanolic Acid
  • Mutation
  • Medicinal & Biomolecular Chemistry
  • HIV-1