title: Synthesis of novel amide functionalized 2H-chromene derivatives by Ritter amidation of primary alcohol using HBF4·OEt2 as a mild and versatile reagent and evaluation of their antimicrobial and anti-biofilm activities.
abstract: A series of novel amide functionalized 2H-chromene derivatives 3 were prepared starting from ethyl-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate 1 via sodium borohydride reduction followed by Ritter amidation using HBF4·OEt2 as a mild and versatile reagent. All the products 3 were screened for antimicrobial activity against various Gram-positive, Gram-negative bacteria and fungal strain. The promising derivatives such as 3f, 3g, 3k, 3l, 3m, 3n and 3o were further screened for minimum bactericidal concentration and bio-film inhibition activity and identified the potential ones. Among all the promising, compound 3g was more potent for antimicrobial, MBC and anti bio-film activities. The structure verses activity relationship of 3g revealed that the presence of two bromine atoms at sixth and R position promotes high activity.
authors.affiliation: Fluoroorganic Division, (AcSIR)CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: K
authors.initials: K
authors.lastname: Ratnakar Reddy
authors.affiliation: Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: Y
authors.initials: Y
authors.lastname: Poornachandra
authors.affiliation: Fluoroorganic Division, (AcSIR)CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: G
authors.initials: G
authors.lastname: Jitender Dev
authors.affiliation: Fluoroorganic Division, (AcSIR)CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: G
authors.initials: G
authors.lastname: Mallareddy
authors.affiliation: Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: Jagadeesh B
authors.initials: JB
authors.lastname: Nanubolu
authors.affiliation: Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: C Ganesh
authors.initials: CG
authors.lastname: Kumar
authors.affiliation: Fluoroorganic Division, (AcSIR)CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India. Electronic address: narsaiah@iict.res.in.
authors.forename: B
authors.initials: B
authors.lastname: Narsaiah
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018441:Biofilms / Q000187:drug effects; D001881:Borates; D001888:Boric Acids / Q000737:chemistry; D002175:Candida / Q000187:drug effects; D002177:Candidiasis / Q000188:drug therapy; D002384:Catalysis; D000431:Ethanol / Q000737:chemistry; D006801:Humans; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular
chemical_list: C412074:5,7-dimethoxy-2-methyl-2H-benzopyran; D000577:Amides; D000890:Anti-Infective Agents; D001578:Benzopyrans; D001881:Borates; D001888:Boric Acids; D000431:Ethanol; C098759:fluoroboric acid
keywords: Amide functionalized 2H-chromene; Chromene-2-ol; HBF(4)·OEt(2) catalyst; Reduction; Ritter amidation