Stereoselective synthesis of alpinoid-C and its analogues and study of their cytotoxic activity against cancer cell lines

Bioorg Med Chem Lett. 2012 Jun 15;22(12):4182-4. doi: 10.1016/j.bmcl.2012.04.021.

S Purushotham Reddy ¹, B Chinnababu, V Shekhar, D Kumar Reddy, G V S Bhanuprakash, L R Velatoor, J Venkateswara Rao, Y Venkateswarlu

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Affiliation

1 Division of Natural Products Chemistry, IICT, Hyderabad 500 007, India.

PMID: 22578452 DOI: 10.1016/j.bmcl.2012.04.021

Abstract

A simple, highly efficient and stereoselective synthetic route has been developed for synthesis of alpinoid-C (1) and its analogues (2, 3 and 4) from commercially available starting Materials by using Wittig olefination, Sharpless asymmetric epoxidation, Grubbs cross metathesis as key steps. All the compounds showed moderate anti-proliferative activity against human leukemia/carcinoma (U-937, THP-1, COLO-205 and HepG2) and mouse melanoma (B16-F10) Cancer cell lines. Compounds 3 and 4 are found to be most potent with an IC(50) of 7.53 μM and 32.26 μM on THP-1, 11.12 μM and 7.21 μM on COLO-205 cell lines, respectively.

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