The Suzuki Cross-Coupling Reaction of l-Ascorbic Acid: C2-Aryl­ation and Evaluation as Antiproliferative Agents

Abstract

Pd 0 catalyst O O O O RO OTf O O O O RO Ar Ar-B(OH) 2 13 examples up to 84% yield anti-cancer screening O O O O MeO O selective inhibitior of HeLa (IC 50 = 6.7 μM) MCF-7 (IC 50 = 6.4 μM) HL-60 (IC 50 = 5.8 μM) cancer cells proliferation 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 IC 50 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.