Pyta Krystian, Blecha Marietta, Janas Anna, Klich Katarzyna, Pecyna Paulina, Gajecka Marzena, Przybylski Piotr
Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland.
Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland.
Bioorg Med Chem Lett. 2016 Sep 1;26(17):4322-6. doi: 10.1016/j.bmcl.2016.07.033. Epub 2016 Jul 17.
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.
已指出在炔基（2）或叠氮基（3）官能化的棉酚骨架上进行铜催化的叠氮化物-炔烃环加成反应（CuAAC）时存在合成限制。合成新型棉酚-三唑共轭物的改进方法得到了具有潜在杀真菌活性的新化合物（24 - 31）。对三唑共轭物24 - 31的光谱研究揭示了它们在溶液中的结构，即烯胺 - 烯胺互变异构体形式的存在以及三唑臂之间的π - π堆积分子内相互作用。新型棉酚 - 三唑共轭物的生物学评价表明，具有三唑 - 苄氧基部分的30和31衍生物对尖孢镰刀菌的效力与咪康唑相当。对棉酚及其衍生物处理后不同真菌菌株中麦角甾醇含量的HPLC评价结果有助于提出这些化合物的抗真菌活性机制。
