824-51-1

Usage

Uses

Used in Pharmaceutical Industry:
6-METHYL-1H-PYRROLO[2,3-B]PYRIDINE is used as a building block for the synthesis of new drugs, leveraging its unique structure and reactivity to create compounds with potential therapeutic effects. Its incorporation into drug molecules can enhance their efficacy and selectivity, contributing to the development of innovative treatments for various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 6-METHYL-1H-PYRROLO[2,3-B]PYRIDINE is utilized as a key component in the synthesis of novel agrochemicals, such as pesticides and herbicides. Its unique properties allow for the creation of more effective and targeted agrochemicals, improving crop protection and yield while minimizing environmental impact.
Used in Organic Materials Synthesis:
6-METHYL-1H-PYRROLO[2,3-B]PYRIDINE is employed as a building block in the synthesis of functional organic materials, such as dyes, sensors, and advanced materials. Its unique structure and reactivity enable the development of materials with enhanced properties, such as improved stability, selectivity, and performance in various applications.
Used in Research and Development:
6-METHYL-1H-PYRROLO[2,3-B]PYRIDINE serves as a valuable research tool in the study of organic chemistry and chemical biology. Its unique structure and reactivity make it an ideal candidate for investigating reaction mechanisms, exploring new synthetic routes, and understanding the fundamental principles governing chemical transformations. This research contributes to the advancement of knowledge in these fields and can lead to the discovery of new applications and technologies.

InChI:InChI=1/C8H8N2/c1-6-2-3-7-4-5-9-8(7)10-6/h2-5H,1H3,(H,9,10)

Upstream product

• 178268-95-6 N'-(3,6-Dimethyl-pyridin-2-yl)-N-methyl-N-phenyl-formamidine 
• 65258-08-4 ethyl N-(3,6-dimethyl-2-pyridyl)formamidate 
• 825-59-2 N-(3,6-dimethyl-pyridin-2-yl)-formamide 
• 1332605-39-6 6-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine 
• 1346151-47-0 6-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine 
• 849068-50-4 ethyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate 
• 823-96-1 Trimethylboroxine 
• 55052-27-2 6-chloro-7-azaindole 
• 272-49-1 1H-pyrrolo[3,2-b]pyridine 
• 143468-07-9 6-Chloro-1-methoxycarbonyl-1H-pyrrolo<2,3-b>pyridine 
• 143468-11-5 1-Benzoyl-6-chloro-1H-pyrrolo<2,3-b>pyridine 
• 55052-24-9 1H-Pyrrolo[2,3-b]pyridine-7-oxide 
• 896722-50-2 1-benzenesulfonyl-6-chloro-1H-pyrrolo[2,3-b]pyridine 
• 271-63-6 7-Azaindole 

Downstream Products

• 178268-96-7 6-methyl-1H-pyrrolo[2,3-b]pyridine 7-oxide 
• 300545-98-6 C₂₉H₂₈N₂O₅ 
• 1000340-28-2 3-bromo-6-methyl-1H-pyrrolo[2,3-b]pyridine 
• 1420532-46-2 tert-butyl 2-(1-(2-(acetamidomethyl)-4-methylphenyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate 
• 1420532-47-3 tert-butyl 2-(1-(2-(ethanethioamidomethyl)-4-methylphenyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate 
• 1420532-48-4 ?tert-butyl 2-(1-(2-((3,5-dimethyl-4H-1,2,4-triazol-4-yl)methyl)-4-methylphenyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate 
• 1420532-35-9 1-(2-((1,4-dimethyl-1H-pyrazol-5-yl)methyl)-4-fluorophenyl)-6-methyl-1H-pyrrolo[2,3-b]pyridine 
• 1420532-28-0 5-bromo-2-(6-methyl-1H-pyrrolo[2,3-b]pyridin-1-yl)benzonitrile 
• 1399849-64-9 1-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone 
• 1255099-47-8 2,6-dimethyl-1H-pyrrolo[2,3-b]pyridine 
• 1346151-47-0 6-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine 
• 1420532-29-1 (5-bromo-2-(6-methyl-1H-pyrrolo[2,3-b]pyridin-1-yl)phenyl)methanamine 
• 171879-99-5 4-chloro-6-methyl-1H-pyrrolo[2,3-b]pyridine 
• 1420070-52-5 N-ethyl-N-[2-(6-methyl-1H-pyrrolo[2,3-b]pyridin-1-yl)-5-(trifluoromethyl)benzyl]cyclopropanecarboxamide 

Relevant academic research and scientific papers

Synthesis of novel 7-azaindole derivatives containing pyridin-3-ylmethyl dithiocarbamate moiety as potent PKM2 activators and PKM2 nucleus translocation inhibitors

Multiple lines of evidence have indicated that pyruvate kinase M2 (PKM2) is upregulated in most cancer cells and it is increasingly recognized as a potential therapeutic target in oncology. In a continuation of our discovery of lead compound 5 and SAR study, the 7-azaindole moiety in compound 5 was systematically optimized. The results showed that compound 6f, which has a difluoroethyl substitution on the 7-azaindole ring, exhibited high PKM2 activation potency and anti-proliferation activities on A375 cell lines. In a xenograft mouse model, oral administration of compound 6f led to significant tumor regression without obvious toxicity. Further mechanistic studies revealed that 6f could influence the translocation of PKM2 into nucleus, as well as induction of apoptosis and autophagy of A375 cells. More importantly, compound 6f significantly inhibited migration of A375 cells in a concentration-dependent manner. Collectively, 6f may serve as a lead compound in the development of potent PKM2 activators for cancer therapy.

Design and Synthesis of Potent and Selective PIM Kinase Inhibitors by Targeting Unique Structure of ATP-Binding Pocket

In the development of kinase inhibitors, one of the major concerns is selectivity. An effective strategy to achieve high selectivity is to utilize structural differences among kinases to inform inhibitor design. Here, we set out to improve the PIM (proviral integration site for Moloney murine leukemia virus) kinase-inhibitory selectivity of our previously reported 7-azaindole derivative 2, which has promising ADMET properties, by targeting a unique bulge in the ATP-binding pocket. 6-Substituted 7-azaindoles, especially the 6-chlorinated derivatives, proved to be potent and selective PIM kinase inhibitors and appear to be promising lead compounds for future drug discovery.

Structure-activity relationships (SAR) and structure-kinetic relationships (SKR) of bicyclic heteroaromatic acetic acids as potent CRTh2 antagonists II: Lead optimization

Extensive structure-activity relationship (SAR) and structure-kinetic relationship (SKR) studies in the bicyclic heteroaromatic series of CRTh2 antagonists led to the identification of several molecules that possessed both excellent binding and cellular potencies along with long receptor residence times. A small substituent in the bicyclic core provided an order of magnitude jump in dissociation half-lives. Selected optimized compounds demonstrated suitable pharmacokinetic profiles.

NEW CRTH2 ANTAGONISTS

The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.

New CRTh2 antagonists

The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.

ANTICANCER AGENT

An anticancer agent comprising a compound represented by the formula (I) [R1 represents hydrogen atom, hydroxyl group, a C1-6alkoxy group and the like; R2 and R3 represents hydrogen atom, a halogen atom, a C1-6alkyl group and the like; R4 represents hydrogen atom, a C1-6alkyl group, a C1-6alkylsulfonyl group and the like; R5 represents hydrogen atom or a substituent; .... represents a single bond or a double bond; R6 and R7 represents hydrogen atom, a C1-6alkyl group and the like; R8 represents hydrogen atom, a C1-6alkyl group and the like; A represents -O-, -S-, or - CH2-; D represents -C= or -N=; X represents methylene group, -O-, or -CO-; Q represents -N= or -C(R8)=; and Y represents a heterocyclic group or amino group], which shows a superior inhibitory activity against pim-1 kinase.

Scaffold-hopping strategy: Synthesis and biological evaluation of 5,6-fused bicyclic heteroaromatics to identify orally bioavailable anticancer agents

Utilizing scaffold-hopping drug-design strategy, we sought to identify a backup drug candidate for BPR0L075 (1), an indole-based anticancer agent. For this purpose, 5,6-fused bicyclic heteroaromatic scaffolds were designed and synthesized through shufflin

Discovery of [3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl] acetic acids as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications

Efforts to identify treatments for chronic diabetic complications have resulted in the discovery of a novel series of highly potent and selective [3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl] acetic acid aldose reductase inhibitors. The lead candidate, [6-methyl-3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyri din-1-yl]acetic acid example 16, inhibits aldose reductase with an IC50 of 8 nM, while being inactive against aldehyde reductase (IC50 > 100 μM), a related enzyme involved in the detoxification of reactive aldehydes.

Anti-tumor compounds

Compounds of the following formula: wherein A, D, Q, T, U, V, W, X, Y, Z, R1, and ---- are as defined herein. This invention also relates to a method of inhibiting tubulin polymerization, or treating cancer or an angiogenesis-related disorder w

The synthesis of 4-benzylamino-6-methyl-1H-pyrrolo[3,2-c]pyridine and 4-benzylamino-6-methyl- 1H-pyrrolo[2,3-b]pyridine

4-Benzylamino-6-methyl-1H-pyrrolo[3,2-c]pyridine (2) and 4-benzylamino-6-methyl-1H-pyrrolo[2,3-b]pyridine (3) were synthesized as deaza analogues of the anxiolytic agent 4-benzylamino-2-methyl-7H-pyrrolo[2,3-d]pyrimidine (1). The 1-deaza analogue (2) was