Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents

M. Vijaya Bhaskar Reddy, Chung Ren Su, Wen Fei Chiou, Yi Nan Liu, Rosemary Yin Hwa Chen, Kenneth F. Bastow, Kuo Hsiung Lee, Tian Shung Wu

Research output: Contribution to journalArticlepeer-review

84 Citations (Scopus)

Abstract

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 IC50 values ranging from 0.03 to 3.80 μg/mL. Structure-activity relationships (SAR) are also discussed.

Original languageEnglish
Pages (from-to)7358-7370
Number of pages13
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number15
DOIs
Publication statusPublished - 2008 Aug 1

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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