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首页> 外文期刊>Russian journal of bioorganic chemistry >Synthesis and antimicrobial activity of new heterocyclic compounds containing thieno[3,2-c]coumarin and pyrazolo[4,3-c]coumarin frameworks
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Synthesis and antimicrobial activity of new heterocyclic compounds containing thieno[3,2-c]coumarin and pyrazolo[4,3-c]coumarin frameworks

机译：含有硫杂环丁[3,2-c]香豆素和吡唑并[4,3-c]香豆素骨架的新型杂环化合物的合成和抑菌活性

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摘要

Reaction of 4-chlorocoumarin-3-carbonitrile with ethyl thioglycolate and ethyl glycinate hydrochloride leads to a series of title products. Hydrazinolysis of amino thienocoumarin carboxylate afforded the hydrazino derivative which underwent various reactions to build new heterocyclic rings containing thienocoumarin moiety. Chloro acetylation of aminoester compound afforded the chloro acetyl amino which underwent nucleophilic substitution reactions with various amines. The following treatment with formaldehyde under Mannich conditions afforded the corresponding imidazo derivatives. Reaction of chloroacetylamino with potassium thiocyanate yielded ethylpyrimidothieno coumarin sulfanylacetate which was used as a versatile precursor for synthesis of other heterocycles. On the other hand, reaction of chloro coumarin carbonitrile with hydrazine gave the aminopyrazolocoumaine which reacted with bifunctionally compounds to give the substituted pyrimido derivatives. Diazotization and coupling of aminopyrazole with ethylcyanoacetate yielded ethylaminotriazinopyrazolocoumarine carboxylate. Several of the compounds obtained demonstrated considerable antifungal and antibacterial activity in the in vitro test systems.
机译：4-氯香豆素-3-腈与硫代乙醇酸乙酯和甘氨酸乙酯盐酸盐的反应产生一系列标题产物。氨基噻吩香豆素羧酸酯的肼解作用提供了肼衍生物，其经历了各种反应以构建新的含有噻吩香豆素部分的杂环。氨基酯化合物的氯乙酰化得到氯乙酰基氨基，该氯乙酰基氨基与各种胺进行了亲核取代反应。在曼尼希条件下用甲醛进行以下处理，得到相应的咪唑衍生物。氯乙酰氨基与硫氰酸钾反应生成乙基嘧啶并没有香豆素硫烷基乙酸酯，其被用作合成其他杂环的通用前体。另一方面，氯香豆素腈与肼反应得到氨基吡唑并香豆素，其与双功能化合物反应得到取代的嘧啶衍生物。将氨基吡唑重氮化并与氰基乙酸乙酯偶联，得到乙基氨基三嗪并吡唑并香豆素羧酸盐。在体外测试系统中，获得的几种化合物表现出相当大的抗真菌和抗菌活性。

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