title: Antimicrobial profile of some novel keto esters: Synthesis, crystal structures and structure-activity relationship studies.
abstract: Rapid increase in bacterial resistance has become a major public concern by escalating alongside a lack of development of new anti-infective drugs. Novel remedies in the battle against multidrug-resistant bacterial strains are urgently needed. So, in this context, the present work is towards the investigation of antimicrobial efficacy of some novel keto ester derivatives, which are prepared by the condensation of substituted benzoic acids with various substituted phenacyl bromides in dimethylformamide at room temperature using triethylamine as a catalyst. The structural build-up of the target compounds was accomplished by spectroscopic techniques including FTIR, (1)H and (13)C NMR spectroscopy and mass spectrometry. The purity of the synthesized compounds was ascertained by elemental analysis. The molecular structures of compounds (4b) and (4l) were established by X-ray crystallographic analysis. The prepared analogues were evaluated for their antimicrobial activity against Gram-positive (Staphylococcus aureus, Micrococcus leuteus) and Gram-negative (Pseudomonas picketti, Salmonella setuball) bacteria and two fungal pathogenic strains (Aspergillus niger, Aspergillus flavus), respectively. Among the screened derivatives, several compounds were found to possess significant activity but (4b) and (4l) turned out to be lead molecules with remarkable antimicrobial efficacy. The structure-activity relationship analysis of this study also revealed that structural modifications on the basic skeleton affected the antimicrobial activity of the synthesized compounds.
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan.
authors.forename: Imtiaz
authors.initials: I
authors.lastname: Khan
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan.
authors.forename: Aamer
authors.initials: A
authors.lastname: Saeed
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan.
authors.forename: Mohammad Ifzan
authors.initials: MI
authors.lastname: Arshad
authors.affiliation: Bio-21 Institute, School of Chemistry, University of Melbourne, Parkville, Victoria, Australia.
authors.forename: Jonathan Michael
authors.initials: JM
authors.lastname: White
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D004952:Esters