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Synthesis of 3-O-propargylated betulinic acid and its 1,2,3-triazoles as potential apoptotic agents.

Abstract
Cytotoxic agents from nature are presently the mainstay of anticancer chemotherapy, and the need to reinforce the arsenal of anticancer agents is highly desired. Chemical transformation studies carried out on betulinic acid, through concise 1,2,3-triazole synthesis via click chemistry approach at C-3position in ring A have been evaluated for their cytotoxic potentiation against nine human cancer cell lines. Most of the derivatives have shown higher cytotoxic profiles than the parent molecule. Two compounds i.e. 3{1N(2-cyanophenyl)-1H-1,2,3-triazol-4yl}methyloxy betulinic acid (7) and 3{1N(5-hydroxy-naphth-1yl)-1H-1,2,3-triazol-4yl}methyloxy betulinic acid (13) displayed impressive IC50 values (2.5 and 3.5 μM respectively) against leukemia cell line HL-60 (5-7-fold higher potency than betulinic acid). As evident from various biological end points, inhibition of cell migration and colony formation, mitochondrial membrane disruption followed by DNA fragmentation and apoptosis, is demonstrated.
AuthorsRabiya Majeed, Payare L Sangwan, Praveen K Chinthakindi, Imran Khan, Nisar A Dangroo, Niranjan Thota, Abid Hamid, Parduman R Sharma, Ajit K Saxena, Surrinder Koul
JournalEuropean journal of medicinal chemistry (Eur J Med Chem) Vol. 63 Pg. 782-92 (May 2013) ISSN: 1768-3254 [Electronic] France
PMID23584541 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2013 Elsevier Masson SAS. All rights reserved.
Chemical References
  • Pentacyclic Triterpenes
  • Triazoles
  • Triterpenes
  • Betulinic Acid
Topics
  • Apoptosis (drug effects)
  • Cell Line, Tumor
  • Cell Movement (drug effects)
  • Cell Survival (drug effects)
  • DNA Fragmentation (drug effects)
  • Dose-Response Relationship, Drug
  • Electrophoresis, Agar Gel
  • HL-60 Cells
  • Humans
  • Inhibitory Concentration 50
  • MCF-7 Cells
  • Membrane Potential, Mitochondrial (drug effects)
  • Models, Chemical
  • Molecular Structure
  • Pentacyclic Triterpenes
  • Structure-Activity Relationship
  • Triazoles (chemical synthesis, chemistry, pharmacology)
  • Triterpenes (chemical synthesis, chemistry, pharmacology)
  • Betulinic Acid

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