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

Santosh R. Kote; Ganesh R. Dhage; Shankar R. Thopate; Ratnakar Mishra; Ayesha A. Khan

doi:10.1055/s-0034-1380743

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(17): 2603-2608
DOI: 10.1055/s-0034-1380743

paper

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

Santosh R. Kote

^aDepartment of Chemistry, Prof. John Barnabas Post Graduate School for Biological Studies, Ahmednagar College, Ahmednagar, Station Road, Ahmednagar, Maharashtra, 414001, India eMail: srthopate@gmail.com

,

Ganesh R. Dhage

^aDepartment of Chemistry, Prof. John Barnabas Post Graduate School for Biological Studies, Ahmednagar College, Ahmednagar, Station Road, Ahmednagar, Maharashtra, 414001, India eMail: srthopate@gmail.com

,

Shankar R. Thopate*

^aDepartment of Chemistry, Prof. John Barnabas Post Graduate School for Biological Studies, Ahmednagar College, Ahmednagar, Station Road, Ahmednagar, Maharashtra, 414001, India eMail: srthopate@gmail.com

,

Ratnakar Mishra

^bDepartment of Chemistry, University of Pune, Ganeshkhind, Pune, Maharashtra, 411007, India

,

Ayesha A. Khan

^bDepartment of Chemistry, University of Pune, Ganeshkhind, Pune, Maharashtra, 411007, India

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Abstract

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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.

Keywords

antitumor agents - arylation - cross-coupling - lactones - vitamins

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Referenzen

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Supporting Information

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

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