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

Autor:	K, Chennakesava Rao, K, Easwaramoorthi, Y, Arun, C, Balachandran, K S, Muralidhara Rao, M, Govindhan, Nobuhiko, Emi, T, Prakasam, P T, Perumal
Rok vydání:	2015
Předmět:	Mannich Bases Molecular Docking Simulation Structure-Activity Relationship Dose-Response Relationship Drug Molecular Structure Gram-Negative Bacteria Phenylpropanolamine Microbial Sensitivity Tests Boranes Gram-Positive Bacteria Catalysis Anti-Bacterial Agents
Zdroj:	Bioorganicmedicinal chemistry letters. 25(19)
ISSN:	1464-3405
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=pmid________::99cd140c950fad620823363802b40a36 https://pubmed.ncbi.nlm.nih.gov/26296475 Zobrazit plný text záznamu Full Text from ScienceDirect