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Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents.
Bioorg Med Chem. 2008 Aug 01; 16(15):7358-70.BM

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 IC(50) values ranging from 0.03 to 3.80 microg/mL. Structure-activity relationships (SAR) are also discussed.

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Authors+Show Affiliations

Reddy MV
Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan.
Su CR
No affiliation info available
Chiou WF
No affiliation info available
Liu YN
No affiliation info available
Chen RY
No affiliation info available
Bastow KF
No affiliation info available
Lee KH
No affiliation info available
Wu TS
No affiliation info available

MeSH

Antineoplastic AgentsCell Line, TumorChalconesDrug DesignHumansMannich BasesMolecular StructureStructure-Activity Relationship

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18602831

Citation

Reddy, M Vijaya Bhaskar, et al. "Design, Synthesis, and Biological Evaluation of Mannich Bases of Heterocyclic Chalcone Analogs as Cytotoxic Agents." Bioorganic & Medicinal Chemistry, vol. 16, no. 15, 2008, pp. 7358-70.
Reddy MV, Su CR, Chiou WF, et al. Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents. Bioorg Med Chem. 2008;16(15):7358-70.
Reddy, M. V., Su, C. R., Chiou, W. F., Liu, Y. N., Chen, R. Y., Bastow, K. F., Lee, K. H., & Wu, T. S. (2008). Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents. Bioorganic & Medicinal Chemistry, 16(15), 7358-70. https://doi.org/10.1016/j.bmc.2008.06.018
Reddy MV, et al. Design, Synthesis, and Biological Evaluation of Mannich Bases of Heterocyclic Chalcone Analogs as Cytotoxic Agents. Bioorg Med Chem. 2008 Aug 1;16(15):7358-70. PubMed PMID: 18602831.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents. AU - Reddy,M Vijaya Bhaskar, AU - Su,Chung-Ren, AU - Chiou,Wen-Fei, AU - Liu,Yi-Nan, AU - Chen,Rosemary Yin-Hwa, AU - Bastow,Kenneth F, AU - Lee,Kuo-Hsiung, AU - Wu,Tian-Shung, Y1 - 2008/06/14/ PY - 2008/02/04/received PY - 2008/06/10/revised PY - 2008/06/11/accepted PY - 2008/7/8/pubmed PY - 2008/11/8/medline PY - 2008/7/8/entrez SP - 7358 EP - 70 JF - Bioorganic & medicinal chemistry JO - Bioorg Med Chem VL - 16 IS - 15 N2 - 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. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/18602831/Design_synthesis_and_biological_evaluation_of_Mannich_bases_of_heterocyclic_chalcone_analogs_as_cytotoxic_agents_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(08)00566-X DB - PRIME DP - Unbound Medicine ER -