title: Synthesis, antimicrobial and molecular docking studies of enantiomerically pure N-alkylated β-amino alcohols from phenylpropanolamines.
abstract: Enantiomerically pure N-alkylated β-amino alcohols 1a, 1a', 1c, 1c', 1d, 1d', 1e and 1e', with ee 100% have been synthesized from phenylpropanolamines 2. Effect of the neighboring chiral environment on the newly formed chiral center has been studied experimentally and concluded that the newly formed chiral center's absolute configuration is opposite to the adjacent (α- or β-) chiral environment. The antimicrobial activity of the synthesized β-amino alcohols were screened using in vitro disc diffusion method and variable antimicrobial activities were shown for 1a, 1a', 1c, 1c', 1d, 1d', 1e &1e' and amongst them 1d &1d' exhibited significant activity against bacteria and fungi. In silico studies revealed all the synthesized β-amino alcohols 1a-e and 1a'-e' have shown good binding energies ranging from -7.38 to -6.09 kJ/mol towards the target receptor DNA topoisomerase IV and 1d' has shown maximum binding energy -7.38 kJ/mol.
authors.affiliation: Malladi Drugs & Pharmaceuticals Limited, Research & Development Centre, Chennai 600 124, TN, India; Organic Chemistry Division, CSIR-Central Leather Research Institute, Chennai 600 020, TN, India; Division of Microbiology and Cancer Biology, Entomology Research Institute, Loyola College, Chennai 600 034, TN, India.
authors.forename: K
authors.initials: K
authors.lastname: Chennakesava Rao
authors.affiliation: Organic Chemistry Division, CSIR-Central Leather Research Institute, Chennai 600 020, TN, India.
authors.forename: Y
authors.initials: Y
authors.lastname: Arun
authors.affiliation: Malladi Drugs & Pharmaceuticals Limited, Research & Development Centre, Chennai 600 124, TN, India.
authors.forename: K
authors.initials: K
authors.lastname: Easwaramoorthi
authors.affiliation: Division of Microbiology and Cancer Biology, Entomology Research Institute, Loyola College, Chennai 600 034, TN, India.
authors.forename: C
authors.initials: C
authors.lastname: Balachandran
authors.affiliation: Malladi Drugs & Pharmaceuticals Limited, Research & Development Centre, Chennai 600 124, TN, India.
authors.forename: T
authors.initials: T
authors.lastname: Prakasam
authors.affiliation: P.G. & Research Department of Chemistry, The New College (Autonomous), Chennai 600 014, TN, India.
authors.forename: T
authors.initials: T
authors.lastname: Eswara Yuvaraj
authors.affiliation: Organic Chemistry Division, CSIR-Central Leather Research Institute, Chennai 600 020, TN, India. Electronic address: ptperumal@gmail.com.
authors.forename: P T
authors.initials: PT
authors.lastname: Perumal
mesh_terms: D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D010665:Phenylpropanolamine / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000605:Amino Alcohols; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D010665:Phenylpropanolamine
keywords: Antimicrobial activity; DNA topoisomerase IV; Disc diffusion method; Phenylpropanolamine; Reductive amination; β-Amino alcohols