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Molecules 2013, 18(8), 9488-9511; doi:10.3390/molecules18089488

Efficient Synthesis of Boron-Containing α-Acyloxyamide Analogs via Microwave Irradiation

1, 1, 1, 1, 2,3,4, 5,6 and 1,*
1 Department of Chemistry, Tamkang University, New Taipei 25137, Taiwan 2 School of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan 3 Chinese Medicine Research and Development Center, China Medical University, Taichung 404, Taiwan 4 Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan 5 Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan 6 Cancer Center, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan
* Author to whom correspondence should be addressed.
Received: 27 June 2013 / Revised: 2 August 2013 / Accepted: 5 August 2013 / Published: 8 August 2013
(This article belongs to the Section Organic Synthesis)
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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 boron; multicomponent reaction; Passerini reaction; HepG2
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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