含噻吩[3,2-c]香豆素和吡唑[4,3-c]香豆素框架的新杂环化合物的合成及其抑菌活性。

Bioorganicheskaia khimiia Pub Date : 2013-09-01
Adel M Kamal El-Dean, Remon M Zaki, Ahmed A Geies, Shaban M Radwan, Mahmoud S Tolba
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引用次数: 0

摘要

4-氯香豆素-3-碳腈与巯基乙酸乙酯和甘氨酸乙酯盐酸盐反应得到一系列标题产品。氨基硫代香豆素羧酸酯的肼水解得到的肼衍生物经过多种反应构建了含有硫代香豆素部分的杂环。氨基酯化合物的氯乙酰化反应使氯乙酰氨基发生亲核取代反应,得到多种胺。随后在曼尼希条件下用甲醛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硫代香豆素磺酸氨基乙酸酯,作为合成其他杂环化合物的多功能前驱体。另一方面,氯香豆素碳腈与肼反应得到氨基吡唑古缅,与双功能化合物反应得到取代嘧啶衍生物。氨基吡唑与氰乙酸乙酯重氮化偶联制得乙胺三嗪吡唑羧酸酯。所获得的几种化合物在体外测试系统中显示出相当大的抗真菌和抗菌活性。
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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.

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 hydrazine 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 various amines. The following treatment with formaldehyde under Mannich conditions afforded the corresponding imidazo derivatives. Reaction of Ghloroacetylamino 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 carbo nitrile 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.

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