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Synthesis and anticancer activity of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of α-santonin.

Abstract
In the present study, novel spiro derivatives of α-santonin were prepared and tested for their anticancer activity against a panel of six human cancer cell lines. Spiro-isoxazoline and spiro-isoxazolidine derivatives have been generated on C-ring of α-santonin (α-methylene-γ-butyrolactone) by the 1,3-dipolar cycloaddition of α-santonin derivative 6 with nitrile oxides 7 and nitrones 9 respectively. Among all, compound 10b″ had shown IC50 of 0.01, 0.5 and 0.3 μM against PC-3, THP-1 and MCF-7 cell lines respectively. Further, flow cytometry studies showed that PC-3 cells treated with the spiro-isoxazolidine derivative 10b″ were arrested in the sub G1 phase of the cell cycle in a concentration dependent manner. The spiro-isoxazolidine derivative 10b″ also showed concentration dependent inhibitory activity against NF-κB, p65 with 57% inhibition in 24 h at 10 μM.
AuthorsJabeena Khazir, Parvinder Pal Singh, D Mahendhar Reddy, Irfan Hyder, Syed Shafi, S D Sawant, Gousia Chashoo, Ajay Mahajan, M S Alam, A K Saxena, S Arvinda, B D Gupta, H M Sampath Kumar
JournalEuropean journal of medicinal chemistry (Eur J Med Chem) Vol. 63 Pg. 279-89 (May 2013) ISSN: 1768-3254 [Electronic] France
PMID23501113 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2013 Elsevier Masson SAS. All rights reserved.
Chemical References
  • Antineoplastic Agents
  • Isoxazoles
  • Transcription Factor RelA
  • Santonin
Topics
  • Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
  • Cell Cycle Checkpoints (drug effects)
  • Cell Line, Tumor
  • Cell Survival (drug effects)
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Flow Cytometry
  • G1 Phase (drug effects)
  • Humans
  • Inhibitory Concentration 50
  • Isoxazoles (chemical synthesis, chemistry, pharmacology)
  • MCF-7 Cells
  • Models, Chemical
  • Molecular Conformation
  • Molecular Structure
  • Santonin (chemical synthesis, chemistry, pharmacology)
  • Stereoisomerism
  • Transcription Factor RelA (antagonists & inhibitors, metabolism)

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