New Indole compounds with acidic terminal

Abstract

Indoles are important heterocyclic molecules modified by many researchers to a lot of derivatives used in all the fields of the life including medical, therapeutic and industrial application. This work is continuous effort to what was began before aiming to the synthesis of benzo indole derivatives by coupling with some amino acids core including alanin, valine and tryptophanvia Schiff reaction in order to find new potential anticancer agents. Schiff reaction happen between aldehyde and amine groups so that benzo indole (1, 1, 2-trimethyl-1H-benzo[e]indole) (1) need a instead of to functionalization to create two aldehyde groups by treatment with phosphoryl chloride (POCl3), this treatment yield the precursors 2-(1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene) malonaldehyde (2), which is capable of applying Schiff reaction. The 3D investigation of the precursors shows the aldehyde group close to the methyl group is under steric hindrance, so that it needs longer time for coupling with amino acids from the other aldehyde group. This property allow the control of the coupling,there for it is possible to synthesize both the coupling so that we could synthesis both mono and di-substituted through the reaction of the precursors 2-(1, 1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene) malonaldehyde (2) with each mentioned aromatic amines. As a results, four pure compounds have been synthesized and characterized using both 1H and 13C NMR spectroscopy. Two of the products are proven to have a good ability in a human liver cancer cell line HepG2 inhibition at the optimize temperature degree 37Cº within the 24 hours period which makes them a potential anticancer agents.