Synthesis, reactions, and antimicrobial activity of some novel pyrazolo[3,4‐d]pyrimidine, pyrazolo[4,3‐e][1,2,4]triazolo[1,5‐c]pyrimidine, and pyrazolo[4,3‐e][1,2,4]triazolo[3,4‐c]pyrimidine derivatives,Journal of Heterocyclic Chemistry

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Synthesis, reactions, and antimicrobial activity of some novel pyrazolo[3,4‐d]pyrimidine, pyrazolo[4,3‐e][1,2,4]triazolo[1,5‐c]pyrimidine, and pyrazolo[4,3‐e][1,2,4]triazolo[3,4‐c]pyrimidine derivatives
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2019-12-10 , DOI: 10.1002/jhet.3835
Hamdi M. Hassaneen ₁ , Fatma M. Saleh ₁ , Tayseer A. Abdallah ₁ , Yasmin Sh. Mohamed ₂ , Enas M. Awad ₃

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Treatment of N‐phenyl‐substituted benzenecarbo‐hydrazonoyl chlorides 1a‐d with malononitrile in sodium ethoxide solution gave 5‐amino‐4‐cyanopyrazole derivatives 2‐5. Compounds 2‐5 were converted to formidate derivatives 6‐9 upon treatment with TEOF in acetic anhydride. The reaction of the latter products 6‐9 with hydrazine hydrate gave imino‐amino derivatives 10‐13, which was converted to hydrazino derivatives 14‐17 by refluxing with hydrazine hydrate. Hydrazino as well as imino‐amino derivatives undergo condensation, cyclization, and cycloaddition reactions to give pyrazolo[3,4‐d]pyrimidine 18‐21, pyrazolo[4,3‐e][1,2,4]triazolo‐[3,4‐c]pyrimidine 22‐27, and pyrazolo[3′,4′:4,5]pyrimido[1,6‐b][1,2,4]triazine 42‐44 derivatives. Antimicrobial studies are performed using two Gram‐positive bacteria and two Gram‐negative bacteria. Data indicated that compounds 5, 28D, 29B, and 31D are exploring elevated antibacterial effects against all strains tested. Compound 28D is the most promising antibacterial agent against the delicate bacterial strain Bacillus subtilis and Pseudomonas aeruginosa with high effectiveness (low minimum inhibitory concentration [MIC] value) 40 and 60 μg/mL, respectively.

中文翻译：

某些新型吡唑并[3,4- [d]嘧啶，吡唑并[4,3-e] [1,2,4]三唑并[1,5-c]嘧啶和吡唑并[4， 3‐e] [1,2,4]三唑并[3,4‐c]嘧啶衍生物

的治疗Ñ苯基-取代的benzenecarbo-腙酰氯1A - d与丙二腈在乙醇钠溶液，得到5-氨基-4-氰基吡唑衍生物2 - 5。化合物2 - 5转化为formidate衍生物6 - 9处理后与TEOF在乙酸酐。后者产物的反应6 - 9与水合肼，得到亚氨基氨基衍生物10 - 13，将其转化为肼衍生物14 - 17通过与水合肼回流。肼基以及亚氨基氨基衍生物进行缩合，环化，和环加成反应，得到吡唑并[3,4- d ]嘧啶18 - 21，吡唑并[4,3- ë ] [1,2,4]三唑并[3 ，4- ç ]嘧啶22 - 27，和吡唑并[3'，4'：4,5]嘧啶并[1,6- b ] [1,2,4]三嗪42 - 44个衍生物。使用两种革兰氏阳性细菌和两种革兰氏阴性细菌进行抗微生物研究。数据表明，化合物5，28D，29B，和31D正在探索提高对所有测试菌株的抗菌效果。化合物28D是最有希望的抗菌剂，分别对付枯草芽孢杆菌和铜绿假单胞菌，分别具有40μg/ mL和60μg/ mL的高效率（最低抑菌浓度[MIC]值低）。

更新日期：2019-12-11

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