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Synthesis 2015; 47(17): 2603-2608
DOI: 10.1055/s-0034-1380743
DOI: 10.1055/s-0034-1380743
paper
The Suzuki Cross-Coupling Reaction of l-Ascorbic Acid: C2-Arylation and Evaluation as Antiproliferative Agents
Further Information
Publication History
Received: 04 January 2015
Accepted after revision: 13 April 2015
Publication Date:
27 May 2015 (online)
Abstract
The C2-arylation of l-ascorbic acid, via the Suzuki cross-coupling reaction of 3-O-alkyl-5,6-O-isopropylidene-2-O-triflyl-l-ascorbic acid with boronic acids, was investigated. Various arylboronic acids were efficiently coupled under the present protocol. The biological screening results revealed that these compounds were selective anticancer agents. The most potent compound (R)-5-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(furan-2-yl)-4-methoxyfuran-2(5H)-one exhibits IC50 values of 6.7, 6.4, and 5.8 μM against human cervical cell line (HeLa), breast cancer cell line (MCF-7), and leukemic cell line (HL-60), respectively.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380743.
- Supporting Information
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