Hishmat O H, Ebeid M Y, Nakkady S S, Fathy M M, Mahmoud S S
Natural Products Department, National Research Centre, Cairo Egypt.
Boll Chim Farm. 1999 Jun;138(6):259-66.
Formylation of 6-methoxy-1-methyl and 5-methyl,2,3-diphenyl-1H-indole (Ib and IX) gave the 5- and 6- carboxaldehyde derivatives (II and X) respectively, which were treated with ethyl cyanoacetate to form the corresponding 2-cyano-3-substituted acrylic acid ethyl ester (III and XI). The latter compounds reacted with hydrazine hydrate, urea and thiourea to form the corresponding 5-amino-4-substituted 2,4,dihydropyrazol-3- one (IV), 6-indolyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile s (V and XII) and 6-indolyl-4-oxo-2-thixo-1,2,3,4-tetrahydropyrimidine-5-ca rbonitriles (VI and XIII). Reaction of the 5- and 6-carboxaldehyde derivatives with malononitrile afforded the 2-substituted malononitrile derivatives (VII and XIV). VII and XIV reacted readilly with aromatic ketones to give the 2-amino4,6-disubstituted nicotinonitriles (VIII a,b and XVa,b). The biological activity of compounds Ia, Ib, II, III, IX and X was tested for antiinflammatory, ulcerogenic and antispasmodic activities.
6-甲氧基-1-甲基和5-甲基-2,3-二苯基-1H-吲哚（Ib和IX）的甲酰化反应分别得到5-和6-羧醛衍生物（II和X），将它们用氰基乙酸乙酯处理以形成相应的2-氰基-3-取代丙烯酸乙酯（III和XI）。后一种化合物与水合肼、尿素和硫脲反应，形成相应的5-氨基-4-取代-2,4-二氢吡唑-3-酮（IV）、6-吲哚基-2,4-二氧代-1,2,3,4-四氢嘧啶-5-腈（V和XII）以及6-吲哚基-4-氧代-2-硫代-1,2,3,4-四氢嘧啶-5-腈（VI和XIII）。5-和6-羧醛衍生物与丙二腈反应得到2-取代丙二腈衍生物（VII和XIV）。VII和XIV与芳香酮容易反应，得到2-氨基-4,6-二取代烟腈（VIII a,b和XV a,b）。测试了化合物Ia、Ib、II、III、IX和X的抗炎、致溃疡和抗痉挛活性。
