新型[1,2,4]三唑并[1,5 - ][1,2,4,5]四嗪的合成及其抑菌活性研究。
Synthesis of novel [1,2,4]triazolo[1,5-][1,2,4,5]tetrazines and investigation of their fungistatic activity.
作者信息
Korotina Anna V, Tolshchina Svetlana G, Ishmetova Rashida I, Evstigneeva Natalya P, Gerasimova Natalya A, Zilberberg Natalya V, Kungurov Nikolay V, Rusinov Gennady L, Chupakhin Oleg N, Charushin Valery N
机构信息
Laboratory of Heterocyclic Compounds, Postovsky Institute of Organic Synthesis, Russian Academy of Sciences, Ural Branch, S. Kovalevskaya str. 22/20, Yekaterinburg, 620108, Russian Federation.
Experimental Laboratory Department, Ural Research Institute of Dermatovenerology and Immunopathology, Shcherbakova str. 8, Yekaterinburg, 620076, Russian Federation.
出版信息
Beilstein J Org Chem. 2022 Mar 1;18:243-250. doi: 10.3762/bjoc.18.29. eCollection 2022.
A series of novel [1,2,4]triazolo[1,5-][1,2,4,5]tetrazines has been synthesized through oxidation reaction of the corresponding 3,6-disubstituted 1,2,4,5-tetrazines bearing amidine fragments. It is shown that the heterocyclic systems obtained can be modified easily at C(3) position in the reactions with aliphatic alcohols and amines. Also, the reactivity of [1,2,4]triazolo[1,5-][1,2,4,5]tetrazines towards CH-active compounds has been studied. The obtained triazolo[1,5-]annulated 1,2,4,5-tetrazines proved to be active in micromolar concentrations in vitro against filamentous anthropophilic and zooanthropophilic dermatophyte fungi (, and ), which cause skin and its appendages (hair, nails) diseases.
通过对带有脒片段的相应3,6-二取代1,2,4,5-四嗪进行氧化反应，合成了一系列新型的[1,2,4]三唑并[1,5-][1,2,4,5]四嗪。结果表明，所得到的杂环体系在与脂肪醇和胺的反应中，能够在C(3)位轻松实现修饰。此外，还研究了[1,2,4]三唑并[1,5-][1,2,4,5]四嗪对CH-活性化合物的反应活性。所得到的三唑并[1,5-]稠合的1,2,4,5-四嗪在体外对丝状嗜人及嗜动物皮肤癣菌（、和）具有微摩尔浓度的活性，这些真菌会引发皮肤及其附属器（毛发、指甲）疾病。
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