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Efficient Synthesis of Boron-Containing α-Acyloxyamide Analogs via Microwave Irradiation
Department of Chemistry, Tamkang University, New Taipei 25137, Taiwan
School of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan
Chinese Medicine Research and Development Center, China Medical University, Taichung 404, Taiwan
Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan
Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan
Cancer Center, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan
* Author to whom correspondence should be addressed.
Received: 27 June 2013; in revised form: 2 August 2013 / Accepted: 5 August 2013 / Published: 8 August 2013
Abstract: In this report, a Passerini three-component reaction utilizing boron-containing carboxylic acids or aldehydes is discussed. The reaction was carried out in water and facilitated by the use of microwave irradiation. This methodology allowed for the efficient formation of a broad range of boron-containing α-acyloxyamides under mild conditions within a short time. Two series of boron-containing α-acyloxyamides were synthesized and subsequently screened for cytotoxicity using the MTT cell viability assay. Two potential lead compounds were found to have potent activity against the HepG2 cancer cell line, demonstrating the potential of this methodology for use in the development of novel pharmaceuticals.
Keywords: boron; multicomponent reaction; Passerini reaction; HepG2
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MDPI and ACS Style
Chai, C.-C.; Liu, P.-Y.; Lin, C.-H.; Chen, H.-C.; Wu, Y.-C.; Chang, F.-R.; Pan, P.-S. Efficient Synthesis of Boron-Containing α-Acyloxyamide Analogs via Microwave Irradiation. Molecules 2013, 18, 9488-9511.
Chai C-C, Liu P-Y, Lin C-H, Chen H-C, Wu Y-C, Chang F-R, Pan P-S. Efficient Synthesis of Boron-Containing α-Acyloxyamide Analogs via Microwave Irradiation. Molecules. 2013; 18(8):9488-9511.
Chai, Chih-Cheng; Liu, Pin-Yi; Lin, Chia-Hung; Chen, Hsien-Chi; Wu, Yang-Chang; Chang, Fang-Rong; Pan, Po-Shen. 2013. "Efficient Synthesis of Boron-Containing α-Acyloxyamide Analogs via Microwave Irradiation." Molecules 18, no. 8: 9488-9511.