Title

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

Authors

V. Kameshwara Rao
Rakesh Tiwari, University of Rhode Island
Bhupender S. Chhikara, University of Rhode Island
Amir Nasrolahi Shirazi, University of Rhode Island
Keykavous Parang, University of Rhode IslandFollow
Anil Kumar

Document Type

Article

Date of Original Version

6-14-2013

Department

Biomedical and Pharmaceutical Sciences

Abstract

A simple, efficient, and environmentally friendly protocol for the synthesis of 1,3,5-triarylpyrazole in [bimm][PF₆] ionic liquid mediated by Cu(OTf)₂ is described. The reaction protocol gave 1,3,5-triarylpyrazoles in good to high yields (71-82%) via a one-pot addition–cyclocondensation between hydrazines and chalcones, and oxidative aromatization without requirement for an additional oxidizing reagent. The catalyst can be reused up to four cycles without much loss in the catalytic activity. The pyrazoles (4a-o) and pyrazolines (3a-n) were evaluated for antiproliferative activity in SK-OV-3, HT-29, and HeLa human cancer cells lines. Among all compounds, 3b inhibited cell proliferation of HeLa cells by 80% at a concentration of 50 μM.

Citation/Publisher Attribution

Rao, V. K., Tiwari, R., Chhikara, B. S., Shirazi, A. N., Parang, K., & Kumar, A. (2013). Copper(II)triflate-mediated synthesis of 1,3,5-triarylpyrazoles in [bmim][PF₆] ionic liquid and evaluation of their anticancer activities. Royal Society of Chemsitry Advances, 35, 15396-15403. doi: 10.1039/C3RA41830H

Available at: http://dx.doi.org/10.1039/C3RA41830H