- Title
- 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
- Creator
- Al Otaibi, Ahmed; Gordon, Christopher P.; Gilbert, Jayne; Sakoff, Jennette A.; McCluskey, Adam
- Relation
- ARC
- Relation
- RSC Advances Vol. 4, Issue 38, p. 19806-19813
- Publisher Link
- http://dx.doi.org/10.1039/c3ra47418f
- Publisher
- Royal Society of Chemistry
- Resource Type
- journal article
- Date
- 2014
- Description
- 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.
- Subject
- ionic liquids; Knoevenagel condensation; substituted phenyl acetonitriles
- Identifier
- http://hdl.handle.net/1959.13/1302522
- Identifier
- uon:20489
- Identifier
- ISSN:2046-2069
- Language
- eng
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