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: [email protected].
  • 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.