Ergenç N, Salman A, Gürsoy A, Bankaoğlu G
Pharmaceutical Chemistry Department, Faculty of Pharmacy, University of Istanbul, Turkey.
Pharmazie. 1990 May;45(5):346-7.
In connection with previous related works [1-6] we have now studied the reaction of ethyl alpha-benzyl-alpha-acetylethanoate (EBAE), as an aliphatic active C-H compound, with the diazonium salts of p-aminobenzoic acid (PABA), sulfanilamide (SA) and N,N-dimethylsulfanilamide (DSA), respectively. Ethyl 2-benzyl-2-[N-(aryl)hydrazono] ethanoates were the resulting substances (1-3). The synthesis of 4-6, namely 3-phenyl-2,5-disubstituted indoles, was carried out employing acidic indole ring closure reaction (Fischer indole synthesis) starting from 1-3. Because only 5 had a high antifungal potency its derivatives 7-10 were also prepared. But these derivatives were unfortunately found to be inactive. Structure elucidation of 1-10 were made by elemental analysis, IR, NMR and mass spectral data.
结合之前的相关工作[1 - 6]，我们现在研究了作为脂肪族活性碳氢键化合物的α - 苄基 - α - 乙酰基乙酸乙酯（EBAE）分别与对氨基苯甲酸（PABA）、磺胺（SA）和N，N - 二甲基磺胺（DSA）的重氮盐的反应。生成的物质是2 - 苄基 - 2 - [N - （芳基）腙基]乙酸乙酯（1 - 3）。从1 - 3出发，采用酸性吲哚环合反应（费歇尔吲哚合成）进行了3 - 苯基 - 2，5 - 二取代吲哚（4 - 6）的合成。由于只有5具有较高的抗真菌效力，所以还制备了其衍生物7 - 10。但遗憾的是，这些衍生物被发现没有活性。通过元素分析、红外光谱、核磁共振和质谱数据对1 - 10进行了结构解析。
