Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N, Mexico City 11340, Mexico.
Departamento de Fisiología, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Av. Wilfrido Massieu S/N, Mexico City 07738, Mexico.
Molecules. 2023 Oct 23;28(20):7223. doi: 10.3390/molecules28207223.
As a new approach, pyrrolo[1,2-]pyrazines were synthesized through the cyclization of 2-formylpyrrole-based enaminones in the presence of ammonium acetate. The enaminones were prepared with a straightforward method, reacting the corresponding alkyl 2-(2-formyl-1-pyrrol-1-yl)acetates, 2-(2-formyl-1-pyrrol-1-yl)acetonitrile, and 2-(2-formyl-1-pyrrol-1-yl)acetophenones with DMFDMA. Analogous enaminones elaborated from alkyl ()-3-(1-pyrrol-2-yl)acrylates were treated with a Lewis acid to afford indolizines. The antifungal activity of the series of substituted pyrroles, pyrrole-based enaminones, pyrrolo[1,2-]pyrazines, and indolizines was evaluated on six spp., including two multidrug-resistant ones. Compared to the reference drugs, most test compounds produced a more robust antifungal effect. Docking analysis suggests that the inhibition of yeast growth was probably mediated by the interaction of the compounds with the catalytic site of HMGR of the species.
作为一种新方法，通过在醋酸铵存在下，将基于 2-甲酰基吡咯的烯胺酮环化来合成吡咯并[1,2-a]吡嗪。烯胺酮可以通过一种简单的方法制备，即反应相应的烷基 2-(2-甲酰基-1-吡咯-1-基)乙酸酯、2-(2-甲酰基-1-吡咯-1-基)乙腈和 2-(2-甲酰基-1-吡咯-1-基)苯乙酮与 DMFDMA。类似的烯胺酮由烷基 ()-3-(1-吡咯-2-基)丙烯酸酯衍生而来，用路易斯酸处理可得到吲唑啉。对六种 spp.（包括两种多药耐药菌）进行了一系列取代吡咯、吡咯烯胺酮、吡咯并[1,2-a]吡嗪和吲唑啉的抗真菌活性评估。与对照药物相比，大多数测试化合物产生了更强大的抗真菌作用。对接分析表明，酵母生长的抑制可能是通过化合物与 种 HMGR 的催化位点相互作用介导的。
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