Benzylidene indanones and processes for preparation and use thereof

US8633242B2 · kind B2 · utility

Assignee

• COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH · IN

Inventors

• Arvind Singh Negi · Lucknow, IN
• Ayyampudur Palanisamy Prakasham · Lucknow, IN
• Ajit Kumar Saxena · Jammu, IN
• Suaib Luqman · Lucknow, IN
• Debabrata Chanda · Lucknow, IN
• Tandeep Kaur · Jammu, IN
• Atul Gupta · Lucknow, IN

Key dates

• Filing date: Sep 20, 2012
• Grant date: Jan 21, 2014
• Expiry date: Sep 20, 2032

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2602/08
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to benzylidene indanones of general formula 1. The compounds exhibited tubulin polymerisation inhibition. A series of compounds 2-benzylidene 3-(3,4,5-trimethoxyphenyl) indanones having general formula 1 were synthesized from gallic acid through a chemical process. 2-(3,4-Methylenedioxybenzylidine), 3-(3,4,5-trimethoxyphenyl), 4,5,6-trimethoxyindanone (8), a representative compound of this series possessing the molecular formula C29H28O9, was synthesized from gallic acid and exhibits potent anticancer activity. Compound 8 was evaluated for acute oral activity in Swiss albino mice and found to be safe up to 300 mg/kg body weight. The anticancer activity of the compounds has been determined, in order to obtain new potent and cost effective molecules using an in vitro cytotoxicity assay.