Issue 35, 2013
From the journal:

RSC Advances

Copper triflate-mediated synthesis of 1,3,5-triarylpyrazoles in [bmim][PF6] ionic liquid and evaluation of their anticancer activities†

V. Kameshwara Rao,a   Rakesh Tiwari,b   Bhupender S. Chhikara,b   Amir Nasrolahi Shirazi,b   Keykavous Parangb  and  Anil Kumar*a  

* Corresponding authors

a Department of Chemistry, Birla Institute of Technology and Science, Pilani 333031, Rajasthan, India
E-mail: anilkumar@pilani.bits-pilani.ac.in

b Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI, USA

Abstract

A simple, efficient, and environment friendly protocol for the synthesis of 1,3,5-triarylpyrazoles and 1,3,5-triarylpyrazolines in [bmim][PF6] ionic liquid mediated by Cu(OTf)2 is described. The reaction protocol gave 1,3,5-triarylpyrazoles in good to high yields (71–84%) via a one-pot addition–cyclocondensation between chalcones and arylhydrazines, and oxidative aromatization without the requirement for an additional oxidizing reagent. The catalyst can be reused for up to four cycles without much loss in the catalytic activity. The pyrazoles (4a–o) and pyrazolines (3a–n) were evaluated for their antiproliferative activity in SK-OV-3, HT-29, and HeLa human cancer cells lines. Among all the compounds, 3b inhibited cell proliferation of HeLa cells by 80% at a concentration of 50 μM.

Graphical abstract: Copper triflate-mediated synthesis of 1,3,5-triarylpyrazoles in [bmim][PF6] ionic liquid and evaluation of their anticancer activities

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Article information

DOI
https://doi.org/10.1039/C3RA41830H
Article type
Paper
Submitted
16 Apr 2013
Accepted
13 Jun 2013
First published
14 Jun 2013

RSC Adv., 2013,3, 15396-15403

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Copper triflate-mediated synthesis of 1,3,5-triarylpyrazoles in [bmim][PF6] ionic liquid and evaluation of their anticancer activities

V. K. Rao, R. Tiwari, B. S. Chhikara, A. N. Shirazi, K. Parang and A. Kumar, RSC Adv., 2013, 3, 15396 DOI: 10.1039/C3RA41830H

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