Parmar V S, Kumar A, Prasad A K, Singh S K, Kumar N, Mukherjee S, Raj H G, Goel S, Errington W, Puar M S
Department of Chemistry, University of Delhi, India.
Bioorg Med Chem. 1999 Jul;7(7):1425-36. doi: 10.1016/s0968-0896(99)00056-5.
A facile synthesis of (Z)- and (E)-2-(5-arylpyrazol-3-yl)-3-(pyrrol-2-yl)acrylonitriles and (Z)-2-(1,3-diarylpyrazol-5-yl)-3-pyrrol-2-yl)acrylonitriles, and isomerisation of (Z)-2-(5-arylpyrazolyl)acrylonitriles to (E)-2-(5-arylpyrazolyl)acrylonitriles under basic conditions have been reported. (Z)-2-(1,3-Diarylpyrazolyl)acrylonitriles did not undergo isomerisation under the similar conditions. New compounds were identified on the basis of their spectral data (1H-, 13C-, 1H-1H COSY, NOESY, NOE, HMQC NMR, IR, UV and EI mass). The structures of one acrylonitrile and five of their precursor 6-arylpyran-2-ones and cyanomnethylpyrazoles were confirmed by X-ray crystallographic studies. Effects of pyrazolylacrylonitriles and their precursors on rat liver-microsomal lipid peroxidation were evaluated in vitro with a view to establish structure activity relationship and to identify a lead compound.
已报道了(Z)-和(E)-2-(5-芳基吡唑-3-基)-3-(吡咯-2-基)丙烯腈以及(Z)-2-(1,3-二芳基吡唑-5-基)-3-(吡咯-2-基)丙烯腈的简便合成方法，以及(Z)-2-(5-芳基吡唑基)丙烯腈在碱性条件下异构化为(E)-2-(5-芳基吡唑基)丙烯腈的过程。(Z)-2-(1,3-二芳基吡唑基)丙烯腈在类似条件下未发生异构化。根据其光谱数据(1H-、13C-、1H-1H COSY、NOESY、NOE、HMQC NMR、IR、UV和EI质谱)鉴定了新化合物。通过X射线晶体学研究确定了一种丙烯腈及其五种前体6-芳基吡喃-2-酮和氰甲基吡唑的结构。为了建立构效关系并鉴定先导化合物，体外评估了吡唑基丙烯腈及其前体对大鼠肝微粒体脂质过氧化的影响。
