Chemistry Department, Faculty of Science, Mansoura University, El-Gomhoria Street, Mansoura 35516, Egypt.
Eur J Med Chem. 2010 May;45(5):1843-8. doi: 10.1016/j.ejmech.2010.01.021. Epub 2010 Jan 20.
Treatment of 2-cyano-N-(9,10-dioxo-9,10-dihydro-anthracen-2-yl)-acetamide (1) with phenyl isothiocyanate/dimethylsulphate afforded the corresponding ketene N,S-acetal 2 which upon treatment with hydrazine hydrate and 4-aminoantipyrine afforded the pyrazolo derivatives 3 and 4, respectively. 3-aminopyrazole derivative 3 was utilized as key intermediate for the synthesis of pyrazolo[3,4-d]pyrimidine 5, pentaaza-as-indacene 6, triaza-cyclopenta[c]phenanthrene 7, pyrazolo[1,5-a]pyrimidine 8, 9 and (dimethyl-pyrrol-1-yl)pyrazole 10 derivatives. Furthermore, treatment of 1 with DMF/DMA gave the corresponding acrylamide derivative 11 which upon treatment with hydrazine hydrate afforded the corresponding 3-aminopyrazole derivative 12. Moreover, coupling of 1 with 4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-diazonium chloride gave the hydrazone derivative 13 which upon cyclization with acetic acid afforded the corresponding pentaaza-fluorene derivative 14. Representative compounds of the synthesized products were evaluated as antimicrobial agents. Some of these compounds exhibited promising activities.
用苯异硫氰酸酯/二甲亚砜处理 2-氰基-N-(9,10-二氧代-9,10-二氢蒽-2-基)乙酰胺（1），得到相应的酮烯 N,S-缩醛 2，后者与水合肼和 4-氨基安替比林反应，分别得到吡唑衍生物 3 和 4。3-氨基吡唑衍生物 3 被用作合成吡唑并[3,4-d]嘧啶 5、五氮杂-苯并吲哚 6、三氮杂环戊[c]菲 7、吡唑并[1,5-a]嘧啶 8、9 和（二甲基-吡咯-1-基）吡唑 10 衍生物的关键中间体。此外，用 DMF/DMA 处理 1 得到相应的丙烯酰胺衍生物 11，后者与水合肼反应得到相应的 3-氨基吡唑衍生物 12。此外，1 与 4,6-二甲基-1H-吡唑并[3,4-b]吡啶-3-重氮氯化物偶联得到腙衍生物 13，后者与乙酸环化得到相应的五氮杂芴衍生物 14。合成产物的代表性化合物被评估为抗菌剂。其中一些化合物表现出有希望的活性。
