Synthesis and cytotoxicity of triterpenoids derived from betulin and betulinic acid via click chemistry.

Abstract

In this study, a series of triazole substituted betulin and betulinic acid derivatives was designed and synthesized via click chemistry at C-30 position. Eighteen target compounds were evaluated in vitro for their antitumor activities against leukemia cell-line HL-60. Seventeen compounds have not reported before. The cytotoxic experiment showed that most of betulinic acid derived triazoles have higher cytotoxic profile than betulinic acid. Among them, compound 30-[4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl] betulinic acid (7b) showed the best IC50 value (1.3 μM) against leukemia cell-line HL-60 (eight- to ninefold higher potency than betulinic acid).

• Authors: Wei Shi, Ning Tang, Wei-Dong Yan
• Journal: Journal of Asian natural products research (J Asian Nat Prod Res) Vol. 17 Issue 2 Pg. 159-69 ( 2015) ISSN: 1477-2213 [Electronic] England
• PMID: 25379995 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Pentacyclic Triterpenes
• Triazoles
• Triterpenes
• betulin
• Betulinic Acid

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Click Chemistry
• Drug Screening Assays, Antitumor
• HL-60 Cells
• Humans
• Molecular Structure
• Pentacyclic Triterpenes
• Structure-Activity Relationship
• Triazoles (chemistry)
• Triterpenes (chemical synthesis, chemistry, pharmacology)
• Betulinic Acid