title: Synthesis and in vitro antimicrobial activities of new (cyano-NNO-azoxy)pyrazole derivatives.
abstract: The antibacterial and antifungal activity of a series of products, in which the 1,5-dimethyl-4-(cyano-NNO-azoxy)pyrazol-3-yl and 1,3-dimethyl-4-(cyano-NNO-azoxy)pyrazol-5-yl moieties were linked to pyridine, pyrazole, isoxazole, thiophene and the furan ring, were examined. No molecule displayed activity against the gram-negative bacteria tested. Conversely, some compounds displayed activity against two Staphylococcus aureus strains, including the methicillin resistant strain. All compounds displayed interesting antifungal activity, the most active compound of the series being the thiophene derivative 7a. This compound's activity against Candida krusei and Candida glabrata (MIC=0.25 and 0.5 μg/mL, respectively), two fungal species resistant to azoles, is noteworthy. The presence of the cyano function appeared essential for activity.
authors.affiliation: Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, via Pietro Giuria 9, I-10125 Turin, Italy. donatella.boschi@unito.it
authors.forename: Donatella
authors.initials: D
authors.lastname: Boschi
authors.forename: Stefano
authors.initials: S
authors.lastname: Guglielmo
authors.forename: Stefania
authors.initials: S
authors.lastname: Aiello
authors.forename: Giulia
authors.initials: G
authors.lastname: Morace
authors.forename: Elisa
authors.initials: E
authors.lastname: Borghi
authors.forename: Roberta
authors.initials: R
authors.lastname: Fruttero
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects*
chemical_list: D000890:Anti-Infective Agents; D000935:Antifungal Agents; D001391:Azo Compounds; D009570:Nitriles; D011720:Pyrazoles; C059090:phenylazoxycyanide