Synthetic and biological activity evaluation studies on novel 1,3-diarylpropenones.

Abstract

Fourteen novel C-prenylated and O-allylated 1,3-diarylpropenones (chalcones) were synthesized by Claisen-Schmidt condensation reaction of C-prenylated/O-allylated acetophenones with appropriate aldehydes; twelve of these model chalcones were screened in an assay based on the confrontation of invasive human MCF-7/6 mammary carcinoma cells with fragments of normal embryonic chick heart in vitro. Out of the twelve chalcones tested, three were found to exhibit potent anti-invasive activity. Some of these chalcones and their precursor acetophenones were also tested for inhibition of initiation of lipid peroxidation in rat liver microsomes; a prenylated acetophenone carrying two methoxy groups and two free phenolic hydroxy functions was found to be a potential antioxidant.

• Authors: S Mukherjee, V Kumar, A K Prasad, H G Raj, M E Bracke, C E Olsen, S C Jain, V S Parmar
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 9 Issue 2 Pg. 337-45 (Feb 2001) ISSN: 0968-0896 [Print] England
• PMID: 11249126 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Acetophenones
• Antineoplastic Agents
• Antioxidants
• Chalcone

Topics

• Acetophenones (pharmacology)
• Animals
• Antineoplastic Agents (chemical synthesis, pharmacology)
• Antioxidants (chemical synthesis, pharmacology)
• Breast Neoplasms (pathology)
• Chalcone (chemical synthesis, pharmacology)
• Chick Embryo
• Coculture Techniques
• Combinatorial Chemistry Techniques
• Drug Evaluation, Preclinical
• Female
• Humans
• Lipid Peroxidation (drug effects)
• Microsomes, Liver (drug effects, metabolism)
• Myocardium (cytology)
• Neoplasm Invasiveness (prevention & control)
• Rats
• Structure-Activity Relationship
• Tumor Cells, Cultured (drug effects)