Synthesis of BF3 catalyzed Mannich derivatives with excellent ee from phenylpropanolamine, study of their antimicrobial activity and molecular docking

K. Chennakesava Rao, K. Easwaramoorthi, Y. Arun, C. Balachandran, K. S. Muralidhara Rao, M. Govindhan, Nobuhiko Emi, T. Prakasam, P. T. Perumal

研究成果: Article査読

3 被引用数 (Scopus)

抄録

Antimicrobial agents 4a-g and 5a-g with very good potency were synthesized with 100% ee from phenylpropanolamine (norephedrine) by BF3 catalyzed three components one pot Mannich reaction in good yields. Obtained compounds were characterized using spectral techniques. Antimicrobial study of these compounds revealed a good to very high potential activity against tested microbes when compared to standard antimicrobial drugs streptomycin and ketoconazole. These synthesized compounds exhibited significant minimum inhibitory concentration (MIC) values against Gram positive and Gram negative bacteria. Amongst compound 4b, 4c, 4d, 4e, 5a, and 5e exhibited very high potent MIC values against tested twelve bacteria and three fungi when compared to control. When subjected to molecular docking, in silico studies revealed significant binding energies ranging from -7.06 to -8.90 kcal/mol for all obtained compounds towards target receptor DNA topoisomerase IV and amongst compounds 4b and 4d have shown maximum binding energies 8.70 and 8.90 kcal/mol, respectively.

本文言語English
ページ(範囲)4232-4238
ページ数7
ジャーナルBioorganic and Medicinal Chemistry Letters
25
19
DOI
出版ステータスPublished - 1 10月 2015

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