Abstract
A series of 7-azaindolyl hydrazones were prepared by reacting of hydrazides of 7-azaindole-3-acetic acids with aromatic aldehydes and N-substituted indolyl-3-carboxyaldehydes. Structure of all the synthesized compounds were satisfactorily correlated by IR, 1H NMR, 13C NMR and mass spectroscopic evidences. The synthesized compounds were evaluated for their possible anticancer potential against MCF-7 induced breast carcinoma. It is worth mentioning that most of the compounds were considerably active against MCF-7 cell line with GI50 values ranging from 22.3–81.0 μM. The hydrazones of N-1-substituted indole-3-carboxyaldehydes 9f, 9g, 9h, 9c, and 9j were active against MCF-7 cell line with GI50 values less than 40 μM (GI50 = 22.3 and 24.9, 29.6, 30.2 and 37.8 μM respectively) with moderate TGI values (TGI = 56.6, 59.5, 65.5, 70.7 and 94.6 μM respectively). The active compounds were also screened against the normal Vero monkey cell line, which showed moderate selectivity against inhibition of cancer cells.
Highlights
I NDOLE is the most active pharmacophoric nucleus and major constituent of number of bio-molecules viz indole-3-acetic acid (IAA), oncracin-1, indole 3-carbinol (I3C), tryptophan, serotonin and melatonin.[1]
Synthesis of the 2-methyl-7-azaindolyl hydrazide 5 has been accomplished by the chemical reactions outlined in Scheme 1
Mannich reaction of 2-methyl-7-azaindole with N,N-dimethyl amine hydrochloride and paraformaldehyde gave N,N-dimethyl-1-(2-methyl-1H-pyrrolo[2,3-b] pyridin3-yl)methanamine 1 which on treatment with methyl iodide in alcohol followed by substitution with sodium cyanide in DMF furnished 2-methyl-7-azaindole-3-acetonitrile 2
Summary
I NDOLE is the most active pharmacophoric nucleus and major constituent of number of bio-molecules viz indole-3-acetic acid (IAA), oncracin-1, indole 3-carbinol (I3C), tryptophan, serotonin and melatonin.[1] It is found in various natural compounds such as alkaloids.[2] The substituted bis-indole derivatives like nortopsentin, coscinamide A-C, indibulin, rhopaladin, labradorin, tenidap and aplysinopsins exhibited various pharmacological properties such as anti-inflammatory, analgesic and antitumor.[3] One of the preferred approaches during drug development is to synthesize analogues of the lead compound In this regard indole can be replaced with azaindole where the main core would be replaced with bioisosteric conceptual atom and to evaluate the effect on activity.
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