title: Synthesis, structure and antimicrobial evaluation of a new gossypol triazole conjugates functionalized with aliphatic chains and benzyloxy groups.
abstract: Synthetic limitations in the copper-catalyzed azide alkyne cycloaddition (CuAAC) on gossypol's skeleton functionalized with alkyne (2) or azide (3) groups have been indicated. Modified approach to the synthesis of new gossypol-triazole conjugates yielded new compounds (24-31) being potential fungicides. Spectroscopic studies of triazole conjugates 24-31 have revealed their structures in solution, i.e., the presence of enamine-enamine tautomeric forms and π-π stacking intramolecular interactions between triazole arms. Biological evaluation of the new gossypol-triazole conjugates revealed the potency of 30 and 31 derivatives, having triazole-benzyloxy moieties, comparable with that of miconazole against Fusarium oxysporum. The results of HPLC evaluation of ergosterol content in different fungi strains upon treatment of gossypol and its derivatives enabled to propose a mechanism of antifungal activity of these compounds.
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland. Electronic address: k.pyta@amu.edu.pl.
authors.forename: Krystian
authors.initials: K
authors.lastname: Pyta
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland.
authors.forename: Marietta
authors.initials: M
authors.lastname: Blecha
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Janas
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Klich
authors.affiliation: Department of Genetics and Pharmaceutical Microbiology, Poznan University of Medical Sciences, Swiecickiego 4, 60-781 Poznan, Poland.
authors.forename: Paulina
authors.initials: P
authors.lastname: Pecyna
authors.affiliation: Department of Genetics and Pharmaceutical Microbiology, Poznan University of Medical Sciences, Swiecickiego 4, 60-781 Poznan, Poland; Institute of Human Genetics, Polish Academy of Science, Strzeszynska 32, 60-479 Poznan, Poland.
authors.forename: Marzena
authors.initials: M
authors.lastname: Gajecka
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland.
authors.forename: Piotr
authors.initials: P
authors.lastname: Przybylski
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D005658:Fungi / Q000187:drug effects*; D006072:Gossypol / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006898:Hydroxylamines / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000480:Alkynes; D000890:Anti-Infective Agents; D006898:Hydroxylamines; D014230:Triazoles; C017064:benzyloxyamine; D003300:Copper; D006072:Gossypol
keywords: 1,2,3-Triazoles; Antifungal; Gossypol; Mechanism of action; Spectroscopy; π–π stacking