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Fluorinated betulinic acid derivatives and evaluation of their anti-HIV activity.

Publication ,  Journal Article
Li, J; Goto, M; Yang, X; Morris-Natschke, SL; Huang, L; Chen, C-H; Lee, K-H
Published in: Bioorg Med Chem Lett
January 1, 2016

Several fluorinated derivatives of the anti-HIV maturation agent bevirimat (1) were synthesized and evaluated for anti-HIV replication activity. The modified positions were the C-2, C-3, C-28, and C-30 positions, either directly on the betulinic acid (2) skeleton or in the attached side chains. Compound 18, which has a trifluoromethyl group added to C-30 of its isopropenyl group, exhibited similar potency to 1 against HIV-1NL4-3. In total, our current studies support our prior conclusion that C-30 allylic modification is unlikely to be a pharmacophore for anti-HIV activity, but could be a meaningful route to manipulate other properties of 2-related compounds.

Duke Scholars

Published In

Bioorg Med Chem Lett

DOI

EISSN

1464-3405

Publication Date

January 1, 2016

Volume

26

Issue

1

Start / End Page

68 / 71

Location

England

Related Subject Headings

  • Virus Replication
  • Triterpenes
  • Structure-Activity Relationship
  • Pentacyclic Triterpenes
  • Molecular Conformation
  • Microbial Sensitivity Tests
  • Medicinal & Biomolecular Chemistry
  • Halogenation
  • HIV
  • Dose-Response Relationship, Drug
 

Citation

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Li, J., Goto, M., Yang, X., Morris-Natschke, S. L., Huang, L., Chen, C.-H., & Lee, K.-H. (2016). Fluorinated betulinic acid derivatives and evaluation of their anti-HIV activity. Bioorg Med Chem Lett, 26(1), 68–71. https://doi.org/10.1016/j.bmcl.2015.11.029
Li, Jizhen, Masuo Goto, Xiaoming Yang, Susan L. Morris-Natschke, Li Huang, Chin-Ho Chen, and Kuo-Hsiung Lee. “Fluorinated betulinic acid derivatives and evaluation of their anti-HIV activity.Bioorg Med Chem Lett 26, no. 1 (January 1, 2016): 68–71. https://doi.org/10.1016/j.bmcl.2015.11.029.
Li J, Goto M, Yang X, Morris-Natschke SL, Huang L, Chen C-H, et al. Fluorinated betulinic acid derivatives and evaluation of their anti-HIV activity. Bioorg Med Chem Lett. 2016 Jan 1;26(1):68–71.
Li, Jizhen, et al. “Fluorinated betulinic acid derivatives and evaluation of their anti-HIV activity.Bioorg Med Chem Lett, vol. 26, no. 1, Jan. 2016, pp. 68–71. Pubmed, doi:10.1016/j.bmcl.2015.11.029.
Li J, Goto M, Yang X, Morris-Natschke SL, Huang L, Chen C-H, Lee K-H. Fluorinated betulinic acid derivatives and evaluation of their anti-HIV activity. Bioorg Med Chem Lett. 2016 Jan 1;26(1):68–71.
Journal cover image

Published In

Bioorg Med Chem Lett

DOI

EISSN

1464-3405

Publication Date

January 1, 2016

Volume

26

Issue

1

Start / End Page

68 / 71

Location

England

Related Subject Headings

  • Virus Replication
  • Triterpenes
  • Structure-Activity Relationship
  • Pentacyclic Triterpenes
  • Molecular Conformation
  • Microbial Sensitivity Tests
  • Medicinal & Biomolecular Chemistry
  • Halogenation
  • HIV
  • Dose-Response Relationship, Drug