Issue 105, 2016

A recyclable and water soluble copper(i)-catalyst: one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their biological evaluation

Abstract

A facile protocol for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles via a three-component ‘click’ reaction of alkyl/benzyl bromides, sodium azide, and terminal alkynes catalyzed by an efficient water soluble copper(I) complex has been developed. The halides have been directly converted into 1,2,3-triazoles via in situ generation of azides and hence, handling of hazardous azide intermediates can be avoided. Gratifyingly, the inherent advantages of this one-pot process are the use of water as solvent, catalyst recyclability, reduced reaction times, simple recrystallization and high yields of the products. The broad scope of this protocol was also explored for the synthesis of a variety of diversely substituted biologically relevant DNA-interactive 1,2,3-triazolo-tetrahydro-β-carboline derivatives. These 1,2,3-triazolo-tetrahydro-β-carbolines were further evaluated for their in vitro cytotoxicity on selected human cancer cell lines of A-549, HCT-116, BT-549, MDA-MB-231, PC-3, NCI-H460 and HCT-15. DNA binding affinity through viscometry experiment and molecular modeling studies have indicated efficient minor groove binding of these new scaffolds.

Graphical abstract: A recyclable and water soluble copper(i)-catalyst: one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their biological evaluation

Supplementary files

Article information

Article type
Paper
Submitted
14 Sep 2016
Accepted
17 Oct 2016
First published
25 Oct 2016

RSC Adv., 2016,6, 103556-103566

A recyclable and water soluble copper(I)-catalyst: one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their biological evaluation

S. Nekkanti, K. Veeramani, S. Sujana Kumari, R. Tokala and N. Shankaraiah, RSC Adv., 2016, 6, 103556 DOI: 10.1039/C6RA22942E

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