195067-13-1Relevant articles and documents
Indeno[1,2-b]pyridin-4-yl-amine3
Goerlitzer,Herbig,Walter
, p. 504 - 510 (2007/10/03)
The enaminonitrile 1 reacts with ethyl acetoacetate or ethyl β- diethoxypropionate and titanium tetrachloride to yield the indeno[1,2- b]pyridin-4-amines 3 and 4, respectively, while the enaminocarboxylic ester 2 with ethyl acetoacetate under the same conditions forms the 4-pyridone-3- carhoxylic ester 5a. Compound 5a was oxidized by chromic acid to give the indenone 5b. The carboxylic acid 6, obtained by alkaline hydrolysis of 5a, was decarboxylated by heating with quinoline and copper. Under nitrogen 5c was formed, whereas in the presence of oxygen 5d was received. The pyridones 5 are transformed into the 4-chloropyridines 7 using phosphorus oxychloride, which react with N-nucleophiles to yield the secondary indeno[1,2-b]pyfidin- 4-yl-amines 8-11. Compound 8e shows the best activity in vitro on the proliferation of Plasmodium falciparum strains. The EC50-value of 70 ng/ml is comparable with the activity of chloroquine against a multi-drug resistant strain (EC50 = 75 ng/ml). There is also observed a weak growth inhibition of Candida albicans and Staphylococcus aureus by 8c.