27294-02-6

Upstream product

• 2028-84-4 p-methylbenzenediazonium chloride 
• 106-49-0 p-toluidine 
• 620-79-1 Ethyl 2-benzylacetoacetate 

Downstream Products

• 136934-16-2 5-Methyl-1-(2-nitro-phenyl)-3-phenyl-1H-indole-2-carboxylic acid ethyl ester 
• 138653-57-3 1-Cyanomethyl-5-methyl-3-phenyl-1H-indole-2-carboxylic acid ethyl ester 
• 127300-18-9 1-(2-Cyano-ethyl)-5-methyl-3-phenyl-1H-indole-2-carboxylic acid ethyl ester 
• 105492-13-5 5-methyl-3-phenyl-indole-2-carboxylic acid hydrazide 
• 41019-01-6 5-methyl-3-phenyl-indole-2-carbaldehyde 
• 106659-41-0 5-Methyl-3-phenyl-1H-indole-2-carbaldehyde oxime 
• 105492-25-9 N-(5-methyl-3-phenyl-1H-indol-2-yl)-hydrazinecarboxamide 
• 105492-21-5 (5-Methyl-3-phenyl-1H-indol-2-yl)-carbamic acid ethyl ester 
• 105492-17-9 5-Methyl-3-phenyl-1H-indole-2-carbonyl azide 
• 127300-41-8 [1-(3-Amino-propyl)-5-methyl-3-phenyl-1H-indol-2-yl]-methanol 
• 1032291-31-8 C₁₇H₁₄N₄S 
• 138653-76-6 1-(2-Amino-ethyl)-5-methyl-3-phenyl-1H-indole-2-carboxylic acid ethyl ester 
• 138653-65-3 8-Methyl-10-phenyl-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole 
• 136934-26-4 9-Methyl-7-phenyl-5,6-dihydro-indolo[1,2-a]quinoxaline 

Relevant academic research and scientific papers

Novel approach to arylhydrazones, the precursor for Fischer indole synthesis, via diazo esters derived from α-amino acid esters

A novel method for synthesizing arylhydrazones, the precursor for Fischer indole synthesis, using aryllithium reagents and α-diazo esters that are easily obtained from α-amino acid esters, is described.

Novel method for synthesis of aryl hydrazones from α-diazo esters: scope and limitations of nucleophiles

Aryl hydrazones, the precursor of Fischer indole synthesis, were easily obtained by nucleophilic addition of aryllithium reagents to diazo esters. The aryl hydrazones were converted into indoles in good yields by heating with thionyl chloride in alcohol.

Novel synthesis of 5-substituted-3-phenylindole-2-(1,2,4-triazole) derivatives

Various substituted 3-phenylindole 2-carboxylates (1a-c) were prepared according to the literature methods. These carboxylates (1a-c) on reaction with thiosemicarbazide yielded 5-substituted-3-phenylindol-2-(1,2,4-triazole-3- thione) (2a-c) on refluxing in pyridine for 8 h. The 5-substituted-3- phenylindole-2-[1,2,4-triazolo-3-thioacetic acid] (3a-c) were prepared from 5-substituted-3-phenyl indole-2-[1,2,4-triazole-3-thione] (2a-c) on reaction with an appropriate alkylating agent and sodium acetate in acetic acid. Further, (3a-c) were reacted with acetic anhydride to bring about a cyclocondensation reaction to yield 5-substituted-3-phenylindol-2-thiazolo(2,3-b)-triazole (4a-c). The 5-substituted-3-phenylindole-2-[1,2,4-triazolo-3-acetic acid] (3a-c) were reacted with o-phenylenediamino dihydrochloride in ethylene glycol to yield 5-substituted-3-phenylindole-1,2,4-triazolo-3′-yl-thiomethyl) benzimidazoles (5a-c). Copyright Taylor & Francis Group, LLC.

Discovery and SAR of indole-2-carboxylic acid benzylidene-hydrazides as a new series of potent apoptosis inducers using a cell-based HTS assay

A series of indole-2-carboxylic acid benzylidene-hydrazides has been identified as a new class of potent apoptosis inducers through a novel cell-based caspase HTS assay. The screening hit, 5-chloro-3-methyl-indole-2- carboxylic acid (4-nitrobenzylidene)-hydrazide (3a), was found to arrest T47D cells in G2/M and to induce apoptosis as measured by the flow cytometric analysis assay. A SAR study was carried out by modification of the substitutions on the indole and benzene rings. Substitution at the 3-position of the indole ring was found to be important for apoptotic activity. A 20-fold increase of apoptotic activity was achieved from screening hit 3a to 5-methyl-3-phenyl-indole-2-carboxylic acid (4-methylbenzylidene)-hydrazide (9a) and 5-chloro-3-phenyl-indole-2-carboxylic acid (4-nitrobenzylidene)-hydrazide (9b), with EC50 value of 0.1μM in the caspase activation assay in T47D breast cancer cells. Compound 9b also was found to be highly active in a standard growth inhibition assay with a GI50 value of 0.9μM in T47D cells. Compound 3a and its analogs were found to inhibit tubulin polymerization, which is the most probable primary mechanism of action of these compounds.

Substituted indole-2-carboxylic acid benzylidene-hydrazides and analogs as activators of caspases and inducers of apoptosis and the use thereof

The present invention is directed to substituted indole-2-carboxylic acid benzylidene-hydrazides and analogs thereof, represented by the general Formula I: wherein X, Ar1, R2-R6 and R12 are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. The compounds of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.