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Anti-AIDS agents 90. novel C-28 modified bevirimat analogues as potent HIV maturation inhibitors.

Publication ,  Journal Article
Qian, K; Bori, ID; Chen, C-H; Huang, L; Lee, K-H
Published in: J Med Chem
September 27, 2012

In a continuing study of bevirimat (2), the anti-HIV-maturation clinical trials agent, 28 new betulinic acid (BA, 1) derivatives were designed and synthesized. Among these compounds, 17, with a C-28 MEM ester moiety, and 22, with a C-28 ethyl hexanoate, increased the anti-HIV replication activity compared with 2 by 2-fold while compounds 40, 41, 48, and 49, with C-28 piperazine or piperidine amide substitutions, increased the activity by 3- to 15-fold. The best new compound, 41, exhibited an anti-HIV IC(50) of 0.0059 μM compared with 0.087 μM for 2. All of the active compounds showed only antimaturation effects, as confirmed by TZM-bl assay, in blocking the HIV replication. The results suggest that proper C-28 substitutions can further enhance the antimaturation activity of 2 without any antientry effects. Thus, 41 may serve as a promising new lead for development of anti-AIDS clinical trial candidates.

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Published In

J Med Chem

DOI

EISSN

1520-4804

Publication Date

September 27, 2012

Volume

55

Issue

18

Start / End Page

8128 / 8136

Location

United States

Related Subject Headings

  • Virus Replication
  • Triterpenes
  • Succinates
  • Structure-Activity Relationship
  • Medicinal & Biomolecular Chemistry
  • Humans
  • HIV-1
  • Drug Stability
  • Drug Design
  • Cell Line
 

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Qian, K., Bori, I. D., Chen, C.-H., Huang, L., & Lee, K.-H. (2012). Anti-AIDS agents 90. novel C-28 modified bevirimat analogues as potent HIV maturation inhibitors. J Med Chem, 55(18), 8128–8136. https://doi.org/10.1021/jm301040s
Qian, Keduo, Ibrahim D. Bori, Chin-Ho Chen, Li Huang, and Kuo-Hsiung Lee. “Anti-AIDS agents 90. novel C-28 modified bevirimat analogues as potent HIV maturation inhibitors.J Med Chem 55, no. 18 (September 27, 2012): 8128–36. https://doi.org/10.1021/jm301040s.
Qian K, Bori ID, Chen C-H, Huang L, Lee K-H. Anti-AIDS agents 90. novel C-28 modified bevirimat analogues as potent HIV maturation inhibitors. J Med Chem. 2012 Sep 27;55(18):8128–36.
Qian, Keduo, et al. “Anti-AIDS agents 90. novel C-28 modified bevirimat analogues as potent HIV maturation inhibitors.J Med Chem, vol. 55, no. 18, Sept. 2012, pp. 8128–36. Pubmed, doi:10.1021/jm301040s.
Qian K, Bori ID, Chen C-H, Huang L, Lee K-H. Anti-AIDS agents 90. novel C-28 modified bevirimat analogues as potent HIV maturation inhibitors. J Med Chem. 2012 Sep 27;55(18):8128–8136.
Journal cover image

Published In

J Med Chem

DOI

EISSN

1520-4804

Publication Date

September 27, 2012

Volume

55

Issue

18

Start / End Page

8128 / 8136

Location

United States

Related Subject Headings

  • Virus Replication
  • Triterpenes
  • Succinates
  • Structure-Activity Relationship
  • Medicinal & Biomolecular Chemistry
  • Humans
  • HIV-1
  • Drug Stability
  • Drug Design
  • Cell Line