Molecular modifications of 2-arylidene-1-indanones leading to increased cytotoxic potencies

Abstract

A series of 2-arylidene-1-indanones, 1, had been shown previously to display cytotoxic properties towards Molt 4/C8, CEM and L1210 cells. In the present study, two series of analogues of 1 were prepared namely various 2-arylidene-1,3-indandiones, 2, and chalcones, 3. In general, the potencies of compounds 2 and 3 were greater than the analogues bearing the same aryl substituents in series 1. Molecular modeling was undertaken in order to seek explanations for the variation in bioactivities.

Keywords::

• α
• β-Unsaturated ketones
• Indan-2,3-diones
• Chalcones
• Cytotoxicity
• Molecular modeling

Acknowledgements

The authors thank the Canadian Institutes of Health Research for a term grant to J.R. Dimmock, the Fonds voor Weterschappelijk Onderzoek (Vlaanderen, Belgium) for financial support to E. De Clercq and J. Balzarini and Mrs. L. van Berckelaer for excellent technical assistance with the antitumor cell assays. Ms. S. Knowles and Ms. B. McCullough are thanked for typing the manuscript.