Design and synthesis of ring C opened analogues of α-santonin as potential anticancer agents

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Authors

Khazir, Jabeena
Mir, Bilal Ahmad
Pilcher, Lynne A.
Riley, Darren Lyall
Chashoo, Gousia
Islam, Md Ataul
Saxena, Ajit K.
Kumar, H.M.S. (Halmuthur Mahabalarao Sampath)

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Springer

Abstract

Here we describe ring opening reaction of a novel halo triene derivative viz., (3S, 5aS)-8- chloro-3a, 4, 5, 5a-tetrahydro-3, 5a, 9-trimethylnaphtho [1, 2-b] furan-2(3H)-one of α- santonin upon nucleophillic attack with alcohols. Halo-triene was synthesized from α- santonin upon reaction with vilsmeier reagent. The synthesised compounds from ring opening reaction were evaluated for anticancer activity against a panel of four human cancer cell lines (A-549, THP-1, HCT-15, and IMR-13). Most of the compounds exhibited promising anticancer activity against all cancer cells in vitro; however compound. 3d with benzyl substitution showed most potent anticancer activity with an IC50 value of 0.3 μM, 0.51 μM, 0.6 μM and 0.23 μM against A-549, THP-1, HCT- 116 and IMR-13 cell lines respectively.

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Keywords

α-Santonin, Vilsmeier reaction, Aliphatic alcohols, Cytotoxicity

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Citation

Khazir, J., Mir, B.A., Pilcher, L.A., Riley, D.L., Gashoo, G., Islam, M.A., Saxena, A.K. & Kumar, H.M.S. Design and synthesis of ring C opened analogues of α-santonin as potential anticancer agents. Medicinal Chemistry Research (2016) 25: 2030-2041. doi:10.1007/s00044-016-1633-8.