title: Synthesis, structure-activity relationships, and in vitro antibacterial and antifungal activity evaluations of novel pyrazole carboxylic and dicarboxylic acid derivatives.
abstract: A series of pyrazole-3-carboxylic acid and pyrazole-3,4-dicarboxylic acid derivatives were synthesized, the structures were confirmed by their NMR ((1)H and (13)C) and FT-IR spectra, and elemental analyses. The antibacterial and antifungal activities of the compounds against five bacterial and five fungal pathogens were screened using modified agar well diffusion assay. Most of the molecules have inhibitory effects on both standard and clinical Candida albicans strains. However, only the molecules 8, 10, 21, and 22 demonstrate some inhibitory effects on Candida parapsilosis, Candida tropicalis, and Candida glabrata strains. The structure-antifungal activity relationships of the compounds on the C. albicans strains were investigated by electron-conformational method. The pharmacophores and antipharmacophores responsible for the inhibition and non-inhibition of the C. albicans strains were obtained by electronic and geometrical characteristics of the reactive fragments of the molecules. These fragments along with the associated parameters can be used in designing the future more potent antifungal agents. It has been shown that both the positions of electronegative atoms like F and O in the pyrazole substituents and the amount of the associated charges on such atoms are crucial in regulating the strength of antifungal activity for the C. albicans strain.
authors.affiliation: Department of Chemistry, Faculty of Arts and Sciences, Dumlupinar University, 43100 Kutahya, Turkey.
authors.forename: Samet
authors.initials: S
authors.lastname: Mert
authors.affiliation: Department of Chemistry, Faculty of Arts and Sciences, Dumlupinar University, 43100 Kutahya, Turkey.
authors.forename: Rahmi
authors.initials: R
authors.lastname: Kasımoğulları
authors.affiliation: Department of Biology, Faculty of Arts and Sciences, Dumlupinar University, 43100 Kutahya, Turkey.
authors.forename: Tuba
authors.initials: T
authors.lastname: İça
authors.affiliation: Department of Biology, Faculty of Arts and Sciences, Dumlupinar University, 43100 Kutahya, Turkey.
authors.forename: Ferdağ
authors.initials: F
authors.lastname: Çolak
authors.affiliation: Department of Physics, Fatih University, 34500 B. Cekmece, Istanbul, Turkey.
authors.forename: Ahmet
authors.initials: A
authors.lastname: Altun
authors.affiliation: School of Earth Sciences, The Ohio State University, 43210 Columbus, OH, USA. Electronic address: ok.12@osu.edu.
authors.forename: Salim
authors.initials: S
authors.lastname: Ok
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects; D003998:Dicarboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D016984:Enterococcus faecium / Q000187:drug effects; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D003998:Dicarboxylic Acids; D011720:Pyrazoles; C031280:pyrazole
keywords: Antibacterial; Antifungal activity; Pyrazole-3,4-dicarboxylic acid; Pyrazole-3-carboxylic acid; Structure–activity relationship (SAR)