Synthesis, cytotoxic activity and structure-activity relationships of hedychenone analogues

Bioorg Med Chem Lett. 2010 Apr 15;20(8):2525-8. doi: 10.1016/j.bmcl.2010.02.101.

P Prabhakar Reddy ¹, Aditya G Lavekar, K Suresh Babu, R Ranga Rao, J Shashidhar, G Shashikiran, J Madhusudana Rao

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Affiliation

1 Natural Products Laboratory, Division of Organic Chemistry-I, Indian Institute of Chemical Technology, Hyderabad 500 607, India.

PMID: 20303755 DOI: 10.1016/j.bmcl.2010.02.101

Abstract

Hedychenone, a plant-derived labdane diterpenoid, showed potent in vitro cytotoxic activity against cancerous cells. In the present study, a series of analogues have been synthesized by modification of the furanoid ring, double bond and the vinylic methyl functionality of this natural product lead and evaluated for their cytotoxic activities against human Cancer cell lines. The structures of the target compounds were established by IR, (1)H NMR and mass spectral analysis. Majority of the analogues displayed potent activity than the parent compound, hedychenone. Preliminary structure-activity relationship studies indicated that furanoid ring has a greater impact on cytotoxicity than that of the decalone nucleus. However, dimerization through C-8 significantly enhanced the cytotoxic activity of the hedychenone.

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