In 2014,Al Otaibi, Ahmed; Gordon, Christopher P.; Gilbert, Jayne; Sakoff, Jennette A.; McCluskey, Adam published 《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》.RSC Advances published the findings.Name: 2-(3-Bromophenyl)acetonitrile The information in the text is summarized as follows:
The Knoevenagel condensation of a series of substituted Ph 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%) while utilization of the protic ionic liquid Pr ammonium nitrate resulted in reduced yields (0-66%). Screening of the 3-substituted-(1H-pyrrol-2-yl)acrylonitriles analogs 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 analogs 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. The results came from multiple reactions, including the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Name: 2-(3-Bromophenyl)acetonitrile)
According to other reports, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) is used in the preparation of diarylpyrimidines (DAPYs) as HIV-1 non-nucleoside reverse transcriptase inhibitors.Name: 2-(3-Bromophenyl)acetonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts