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Issue 38, 2014
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The influence of ionic liquids on the Knoevenagel condensation of 1H-pyrrole-2-carbaldehyde with phenyl acetonitriles – cytotoxic 3-substituted-(1H-pyrrol-2-yl)acrylonitriles

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Abstract

The Knoevenagel condensation of a series of substituted phenyl acetonitriles with 1H-pyrrole-2-carbaldehyde was examined in seven 1-butyl-3-methylimidazolium based ionic liquids and three protic ionic liquids. Of these [BMIM][Br] and [BMIM][OH], with catalytic piperidine, proved most efficient affording 3-substituted-(1H-pyrrol-2-yl)acrylonitriles 3–17 in good to excellent yields (98%) whilst utilisation of the protic ionic liquid propyl ammonium nitrate resulted in reduced yields (0–66%). Screening of the 3-substituted-(1H-pyrrol-2-yl)acrylonitriles analogues 3–17 against a panel of 11 cancer cell lines and one normal cell line allowed the identification of a series of compounds with broad spectrum cytotoxicity, but more interestingly a significant degree of MCF-7 breast cancer cell line specificity was evident with 6 (7 to >25 fold) and 13 (5.7 to >80 fold). Other analogues show high level of efficacy against specific cell lines with 10 showing excellent activity against MCF-7 (GI50 = 1.7 μM) and A431 (GI50 = 2.8 μM) cell lines. The most promising of the compounds identified herein were the 4-CF3 substituted 10 and the 3,4-dichloro substituted 13 with excellent activities against MCF-7 and A431 cell lines. The 3,4-dichloro-13 was a 0.56 μM potent inhibitor of MCF-7 cell growth.

Graphical abstract: The influence of ionic liquids on the Knoevenagel condensation of 1H-pyrrole-2-carbaldehyde with phenyl acetonitriles – cytotoxic 3-substituted-(1H-pyrrol-2-yl)acrylonitriles

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Publication details

The article was received on 09 Dec 2013, accepted on 27 Mar 2014 and first published on 28 Mar 2014


Article type: Paper
DOI: 10.1039/C3RA47418F
Citation: RSC Adv., 2014,4, 19806-19813
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    The influence of ionic liquids on the Knoevenagel condensation of 1H-pyrrole-2-carbaldehyde with phenyl acetonitriles – cytotoxic 3-substituted-(1H-pyrrol-2-yl)acrylonitriles

    A. Al Otaibi, C. P. Gordon, J. Gilbert, J. A. Sakoff and A. McCluskey, RSC Adv., 2014, 4, 19806
    DOI: 10.1039/C3RA47418F

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