title: Design of potent fluoro-substituted chalcones as antimicrobial agents.
abstract: Owing to ever-increasing bacterial and fungal drug resistance, we attempted to develop novel antitubercular and antimicrobial agents. For this purpose, we developed some new fluorine-substituted chalcone analogs (3, 4, 9-15, and 20-23) using a structure-activity relationship approach. Target compounds were evaluated for their antitubercular efficacy against Mycobacterium tuberculosis H37Rv and antimicrobial activity against five common pathogenic bacterial and three common fungal strains. Three derivatives (3, 9, and 10) displayed significant antitubercular activity with IC50values of ≤16,760. Compounds derived from trimethoxy substituent scaffolds with monofluoro substitution on the B ring of the chalcone structure exhibited superior inhibition activity compared to corresponding hydroxy analogs. In terms of antimicrobial activity, most compounds (3, 9, 12-14, and 23) exhibited moderate to potent activity against the bacteria, and the antifungal activities of compounds 3, 13, 15, 20, and 22 were comparable to those of reference drugs ampicillin and fluconazole.
authors.affiliation: a Tercan Vocational High School, Erzincan University , Erzincan , Turkey.|b Department of Chemistry, Faculty of Science , Ataturk University , Erzurum , Turkey.
authors.forename: Serdar
authors.initials: S
authors.lastname: Burmaoglu
authors.affiliation: c Department of Pharmaceutical Chemistry, Faculty of Pharmacy , Mersin University , Mersin , Turkey.
authors.forename: Oztekin
authors.initials: O
authors.lastname: Algul
authors.affiliation: b Department of Chemistry, Faculty of Science , Ataturk University , Erzurum , Turkey.
authors.forename: Arzu
authors.initials: A
authors.lastname: Gobek
authors.affiliation: b Department of Chemistry, Faculty of Science , Ataturk University , Erzurum , Turkey.
authors.forename: Derya
authors.initials: D
authors.lastname: Aktas Anil
authors.affiliation: d Department of Pharmaceutical Microbiology, Faculty of Pharmacy , Mersin University , Mersin , Turkey.
authors.forename: Mahmut
authors.initials: M
authors.lastname: Ulger
authors.affiliation: c Department of Pharmaceutical Chemistry, Faculty of Pharmacy , Mersin University , Mersin , Turkey.
authors.forename: Busra Gul
authors.initials: BG
authors.lastname: Erturk
authors.affiliation: e Advanced Technology Education, Research, and Application Center, Mersin University , Mersin , Turkey.
authors.forename: Engin
authors.initials: E
authors.lastname: Kaplan
authors.affiliation: d Department of Pharmaceutical Microbiology, Faculty of Pharmacy , Mersin University , Mersin , Turkey.
authors.forename: Aylin
authors.initials: A
authors.lastname: Dogen
authors.affiliation: f Department of Medical Microbiology, Faculty of Medicine , Mersin University , Mersin , Turkey.
authors.forename: Gönül
authors.initials: G
authors.lastname: Aslan
mesh_terms: D000890:Anti-Infective Agents / Q000494:pharmacology*; D047188:Chalcones / Q000737:chemistry / Q000494:pharmacology*; D005461:Fluorine / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D047188:Chalcones; D005461:Fluorine
keywords: Chalcone; SAR; antimicrobial activity; antitubercular activity