Shroff J R, Bandurco V, Desai R, Kobrin S, Cervoni P
J Med Chem. 1981 Dec;24(12):1521-5. doi: 10.1021/jm00144a031.
A series of benzimidoylpyrazoles was synthesized and evaluated as hypoglycemic agents. Methyl 1-(N-cyclohexylbenzimidoyl)-5-methyl-3-pyrazolecarboxylate (13) and methyl 1-[N-(4-methoxyphenyl)benzimidoyl]-5-methyl-3-pyrazolecarboxylate (33) are two of the more interesting compounds. A comparison of these benzimidoylpyrazoles with classical standards (tolazamide, phenformin, and buformin) in several experimental models show that these compounds seem to combine in one molecule some of the biological activities of the beta-cytotrophic sulfonylureas and some of the activities of the biguanides. A synthetic scheme for the preparation of the benzimidolypyrazoles and a preliminary structure-activity relationship are presented.
合成了一系列苯并咪唑基吡唑并作为降血糖剂进行评估。1-(N-环己基苯并咪唑基)-5-甲基-3-吡唑甲酸甲酯(13)和1-[N-(4-甲氧基苯基)苯并咪唑基]-5-甲基-3-吡唑甲酸甲酯(33)是其中两个较有趣的化合物。在几个实验模型中将这些苯并咪唑基吡唑与经典标准品(甲苯磺丁酰胺、苯乙双胍和丁双胍)进行比较，结果表明这些化合物似乎在一个分子中兼具了β-细胞营养性磺酰脲类的一些生物活性和双胍类的一些活性。给出了苯并咪唑基吡唑的合成方案以及初步的构效关系。
