Nitrogen-containing Heterocyclic Compound - Indole And Pyrazole Derivatives, Synthesis And Biological Activity Study

Organic compounds containing nitrogen distribute quite abroadly and include various compounds. Among of them, indoles and pyrazoles are of great importance and they are also hotspots that organic chemists are researching.In the studying of cell apoptosis agent, we have designed and synthesized a series of small molecular compounds, screened out some compounds that possess good bioactivity. We have synthesized three 6-aminoindoles via S_NAr reaction, reduction and cyclization tandem from 2,4-dinitro-cholorobenzene and substituded benzoic acid. In order to expand reactions involveing these compounds, we also have synthesized ethyl 9-hydroxy-2,7-dimethyl-1H-pyrorolo[3,2-f]quinoline-3-carboxylate via the reaction of 6-aminoindole with ethyl acetoacetate in the presence of catalysts. Furthermore, we should put forward there are two possibilities in the closed ring reaction of ethyl 6-(4-ethoxy-4-oxobut-2-en-2-ylamino)-2-methyl-1H-indole-3-carboxylate, namely, in 5 or 7 moiety of indole ring. The result shows that the 7 moiety is attacked selectively and ethyl 2,7-dimethyl-9-oxo-6,9-dihydro-1H-pyrorolo[3,2-f]quinoline-3-carboxylate or ethyl-9-hydroxy-2,7-dimethyl-1H-pyrorolo[3,2-f]quinoline-3-carboxylate has been obtained. The structures of compounds were confirmed by IR, MS and ¹H NMR. We have carried out preliminary biological evaluation and screened out indole derivative ethyl 6-amino-2-phenyl-1H-indole-3-carboxy -late that possess good bioactivity.A lot of natural compounds contain pyrazole structure. Pyrazole derivatives possess many bioactivities. In this paper we first obtaind substituted benzoyl chloride via the reaction of substituted benzoic acid and SOCl₂. Then we have synthesized (E) ethyl 2-aryl-2-hydroxy-methylene-3-oxo-butanoate through the acylation reaction of substituted benzoyl chloride and ethyl acetoacetate. Finally pyrazole derivatives were obtained...