Karadeniz Technical University, Department of Chemistry 61080 Trabzon, Turkey.
Eur J Med Chem. 2010 Nov;45(11):4726-32. doi: 10.1016/j.ejmech.2010.07.018. Epub 2010 Aug 19.
Acetohydrazide derivative containing both antipyrine and triazole nuclei (5) was obtained starting from ethyl hydrazinecarboxylate derivative (2) and 4-aminoantipyrine (1) by three steps. The treatment of compound 5 with CS(2) afforded the conversion of hydrazide function into 5-mercapto-1,3,4-oxadiazole ring leading to the formation of 7. Then, 7 gave the product containing triazolotriazine moiety (9) by the reaction with hydrazine hydrate. The synthesis of the compounds incorporating the 1,3,4-thiadiazole (10a-c), 1,2,4-triazole (11a-c) or 1,3-thiazole (12, 13) nucleus as third heterocycle was performed by the acidic or basic treatment of compounds 6a-c which were obtained from the reaction of 5 with several isothiocyanates, or by the condensation of 6a with two different phenacyl bromides, respectively. The antimicrobial activity study revealed that all the compounds showed good activities except 3-5.
从乙基肼羧酸酯衍生物（2）和 4-氨基安替比林（1）出发，经过三步反应得到含有嘧啶和三唑核的乙酰肼衍生物（5）。化合物 5 与 CS(2)的处理将酰肼功能转化为 5-巯基-1,3,4-恶二唑环，导致 7 的形成。然后，7 与水合肼反应生成含有三唑并三嗪部分的产物（9）。通过对 5 与几种异硫氰酸酯反应得到的化合物 6a-c 的酸性或碱性处理，或者通过 6a 与两种不同的苯甲酰溴的缩合，分别合成了含有 1,3,4-噻二唑（10a-c）、1,2,4-三唑（11a-c）或 1,3-噻唑（12、13）核的化合物。抗菌活性研究表明，除 3-5 外，所有化合物均表现出良好的活性。
