Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents.
The chalcone skeleton (1,3-diphenyl-2-propen-1-one) is a unique template that is associated with various biological activities. We synthesized Mannich bases of heterocyclic chalcones (9-47) using a one-step Claisen-Schmidt condensation of heterocyclic aldehydes with Mannich bases of acetophenones, and tested the target compounds for cytotoxicity against three human cancer cell lines (prostate, PC-3; breast, MCF-7; nasopharynx, KB) and a multi-drug resistant subline (KB-VIN). Out of the 39 chalcones synthesized, 31 compounds showed potent activity against at least one cell line with IC(50) values ranging from 0.03 to 3.80 microg/mL. Structure-activity relationships (SAR) are also discussed.
Reddy
M Vijaya Bhaskar
MV
Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan.
Su
Chung-Ren
CR
Chiou
Wen-Fei
WF
Liu
Yi-Nan
YN
Chen
Rosemary Yin-Hwa
RY
Bastow
Kenneth F
KF
Lee
Kuo-Hsiung
KH
Wu
Tian-Shung
TS
D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D047188:Chalcones / Q000737:chemistry* / Q000494:pharmacology*; D015195:Drug Design; D006801:Humans; D008352:Mannich Bases; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D047188:Chalcones; D008352:Mannich Bases