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Usage

Uses

Used in Pharmaceutical Industry:
2-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine is used as a PTP1B inhibitor for its potential to improve insulin sensitivity and regulate glucose levels. This makes it a promising candidate for the development of treatments for type 2 diabetes and obesity, where the modulation of insulin signaling and energy balance is crucial.
Used in Research and Development:
In the field of drug discovery and development, 2-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine serves as a valuable compound for studying the role of PTP1B in insulin signaling and energy balance. Its unique chemical structure and inhibitory properties provide a foundation for further exploration and optimization to enhance its therapeutic potential and efficacy in treating metabolic disorders.

InChI:InChI=1/C14H12N2O2S/c1-11-10-12-6-5-9-15-14(12)16(11)19(17,18)13-7-3-2-4-8-13/h2-10H,1H3

Upstream product

• 143141-23-5 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine 
• 74-88-4 methyl iodide 
• 98-09-9 benzenesulfonyl chloride 
• 271-63-6 7-Azaindole 
• 23612-48-8 2-methyl-1H-pyrrolo[2,3-b]pyridine 

Downstream Products

• 307951-54-8 3-bromo-2-bromomethyl-1-phenylsulfonylpyrrolo[2,3-b]pyridine 
• 1602486-94-1 1-(1,2-dimethyl-7-azaindol-3-yl)-2-[2-methyl-5-(4-trifluoromethylphenyl)-3-thienyl]perfluorocyclopentene 
• 1602486-95-2 1-(1,2-dimethyl-7-azaindol-3-yl)-2-[2-methyl-5-(4-fluorophenyl)-3-thienyl]perfluorocyclopentene 
• 1592848-00-4 1-(1,2-dimethyl-7-azaindole-3-yl)-2-(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene 
• 1602486-96-3 1-(1,2-dimethyl-7-azaindol-3-yl)-2-[2-methyl-5-(4-methylphenyl)-3-thienyl]perfluorocyclopentene 
• 1592847-98-7 1-(1,2-dimethyl-7-azaindol-3-yl)-2-[2-methyl-5-(4-methoxyphenyl)-3-thienyl]perfluorocyclopentene 
• 943324-08-1 1-benzenesulfonyl-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine 
• 872365-16-7 2-(2-methyl-1-(4-(methylsulfonyl)benzyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid 

Relevant academic research and scientific papers

7-AZAINDOLE-2,7-NAPHTHYRIDINE DERIVATIVE FOR THE TREATMENT OF TUMOURS

The compound 4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,7-naphthyridin-1-ylamine and pharmaceutically usable salts and/or tautomers thereof. The use of this compound for the treatment of tumours, tumour growth, tumour metastases and/or AIDS.

Photochromism of new unsymmetrical diarylethenes based on the hybrid of azaindole and thiophene moieties

A new class of photochromic diarylethenes with both azaindole and thiophene moieties were synthesized to investigate the effects of the substituents on their photochromic behaviors, and their structures were determined by single crystal X-ray diffraction

Synthesis and photochromism of novel unsymmetrical diarylethenes with an azaindole unit

A new class of unsymmetrical photochromic diarylethenes with an azaindole moiety has been firstly synthesized. Their properties, including photochromism, crystal structure, as well as fluorescence, were investigated systematically. The azaindole was conne

Discovery and characterization of NVP-QAV680, a potent and selective CRTh2 receptor antagonist suitable for clinical testing in allergic diseases

Optimization of a 7-azaindole-3-acetic acid CRTh2 receptor antagonist chemotype derived from high throughput screening furnished a highly selective compound NVP-QAV680 with low nM functional potency for inhibition of CRTh2 driven human eosinophil and Th2 lymphocyte activation in vitro. The molecule exhibited good oral bioavailability in the rat, combined with efficacy in rodent CRTh2-dependent mechanistic and allergic disease models and was suitable for clinical development.

7-Azaindole-3-acetic acid derivatives: Potent and selective CRTh2 receptor antagonists

High throughput screening identified a 7-azaindole-3-acetic acid scaffold as a novel CRTh2 receptor antagonist chemotype, which could be optimised to furnish a highly selective compound with good functional potency for inhibition of human eosinophil shape change in whole blood and oral bioavailability in the rat.

Reaction of bromomethylazoles and tosylmethyl isocyanide. A novel heterocyclization method for the synthesis of the core of marine alkaloids variolins and related azolopyrimidines

A novel and efficient synthesis of the pyrido[3′,2′:4,5] pyrrolo[1,2-c]pyrimidine system, the heterocyclic core of the variolin family of marine alkaloids, is described. The route involves the reaction of 3-bromo-2-(bromomethyl)pyrrolo[2,3-b]pyridine and tosylmethyl isocyanide (TosMIC) under phase-transfer conditions. This unprecedented reaction was also used to synthesize a series of new methoxycarbonyl azolopyrimidines by reaction of TosMIC with bromomethylindoles, bromomethylbenzimidazole, and bromomethylpyrazole. Hydrolysis and decarboxylation of 5-bromo-7- methoxycarbonylpyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine obtained by this heterocyclization process and installation of the pyrimidine moiety in the C5 position open an alternative approach to complete a total synthesis of variolin B.

Reaction of 2-bromomethylazoles and TosMIC: A domino process to azolopyrimidines. Synthesis of core tricycle of the variolins alkaloids

(matrix presented) A new reaction of N-protected 2-bromomethylazoles and tosylmethyl isocyanide (TosMIC) leading to the preparation of azolopyrimidines is described. This domino sequence was used to synthesize the pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine core of alkaloids variolins from 4-methoxy-2-methylpyrrolo[2,3-b]pyrimidine in two steps.

Synthesis of 2-substituted-1H-pyrrolo[2,3-b]pyridines: Preparation of 7-azaolivacine analogue and 7-azaindolopyridopyrimidine derivatives

2-Substituted-1H-pyrrolo(2,3-b]pyridines have been prepared from 7-azaindole by lithiation followed by addition of various electrophiles. A 7-azaolivacine analogue and pyrido[3'2':4,5]pyrrolo[1,2-c]pyrido[3,2-d]pyrimidine have also been prepared.