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

ABSTRACT: A simple, efficient, and environment friendly protocol for the synthesis of 1,3,5-triarylpyrazole and 1,3,5-triarylpyrazolines 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 (71-84%) via a one-pot addition-cyclocondensation between chalcones and arylhydrazines, 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 ?M.

SUBMITTER: Rao VK

PROVIDER: S-EPMC3806107 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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

Rao V Kameshwara VK Tiwari Rakesh R Chhikara Bhupender S BS Shirazi Amir Nasrolahi AN Parang Keykavous K Kumar Anil A

RSC advances 20130901 35

A simple, efficient, and environment friendly protocol for the synthesis of 1,3,5-triarylpyrazole and 1,3,5-triarylpyrazolines 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 (71-84%) via a one-pot addition-cyclocondensation between chalcones and arylhydrazines, and oxidative aromatization without requirement for an additional oxidizing reagent. The catalyst can be reused up to fo ...[more]

PMID: 24163734

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