Copper-catalyzed three-component synthesis of aminonaphthoquinone-sulfonylamidine conjugates and in vitro evaluation of their antiproliferative activity

Bioorg Med Chem Lett. 2016 Apr 15;26(8):2072-6. doi: 10.1016/j.bmcl.2016.02.071.

Thachapully D Suja ¹, K V L Divya ², Lakshma V Naik ², A Ravi Kumar ³, Ahmed Kamal ³

Affiliations

1 Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India. Electronic address: tdsuja.iict@gov.in.
2 Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
3 Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India; Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Balanagar, Hyderabad 500 037, India.

PMID: 26948541 DOI: 10.1016/j.bmcl.2016.02.071

Abstract

A series of aminonaphthoquinone-sulfonylamidine conjugates were synthesized via a copper-catalyzed three-component reaction of N-propargyl aminonaphthoquinone, sulfonyl azides and various amines. Majority of the compounds exhibited promising antiproliferative potential when evaluated against a panel of four Cancer cell lines. Docking experiments of representative compounds indicated that the conjugates can occupy the ATP-binding pocket of topoisomerase-II Enzyme.

Keywords

Aminonaphthoquinone; Copper; Multicomponent reactions; Sulfonylamidine; Topoisomerase inhibitor.

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