Synthetic and biological activity evaluation studies on novel 1,3-diarylpropenones.
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.
Department of Chemistry, University of Delhi, India.
S
S
Mukherjee
V
V
Kumar
A K
AK
Prasad
H G
HG
Raj
M E
ME
Bracke
C E
CE
Olsen
S C
SC
Jain
V S
VS
Parmar
D000098:Acetophenones / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis / Q000494:pharmacology; D001943:Breast Neoplasms / Q000473:pathology; D002599:Chalcone / Q000138:chemical synthesis / Q000494:pharmacology*; D002642:Chick Embryo; D018920:Coculture Techniques; D020650:Combinatorial Chemistry Techniques; D004353:Drug Evaluation, Preclinical; D005260:Female; D006801:Humans; D015227:Lipid Peroxidation / Q000187:drug effects; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D009206:Myocardium / Q000166:cytology; D009361:Neoplasm Invasiveness / Q000517:prevention & control*; D051381:Rats; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000098:Acetophenones; D000970:Antineoplastic Agents; D000975:Antioxidants; D002599:Chalcone