271-29-4

Usage

Uses

Used in Pharmaceutical Industry:
6-Azaindole is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its ability to be incorporated into the molecular structure of drugs allows for the creation of novel therapeutic agents with potential applications in treating a range of medical conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, 6-Azaindole serves as a key building block for the construction of more complex organic molecules. Its reactivity and structural properties make it an ideal candidate for use in the synthesis of advanced materials, dyes, and other specialty chemicals.
Used in Research and Development:
6-Azaindole is also utilized in research and development settings, where it can be employed to study the effects of structural modifications on the properties and reactivity of indole-based compounds. This knowledge can be applied to the design of new molecules with tailored properties for specific applications.
Overall, 6-Azaindole is a versatile and valuable compound with a wide range of applications across various industries, including pharmaceuticals, chemical synthesis, and research and development. Its unique properties and reactivity make it an essential tool in the development of new drugs, materials, and other advanced technologies.

InChI:InChI=1/C7H6N2/c1-3-8-5-7-6(1)2-4-9-7/h1-5,9H

Upstream product

• 67058-74-6 1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid 
• 64608-65-7 (2,2-diethoxy-ethyl)-pyrrol-2-ylmethylen-amine 
• 146336-81-4 (E)-3-amino-2-(2-ethoxyethenyl)pyridine 
• 185139-01-9 tert-butyl 2-hydroxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate 
• 86119-84-8 phosphoric acid 
• 10025-87-3 trichlorophosphate 
• 357263-41-3 7-chloro-1H-pyrrolo[2,3-c]pyridine 
• 2530-26-9 3-nitropyridine 
• 1826-67-1 vinyl magnesium bromide 
• 7633-56-9 N-aminoindoline 
• 3430-27-1 3-amino-4-methylpyridine 
• 142078-36-2 2-(2-chloro-3-nitro-4-pyridyl)-N,N-dimethylethenamineine 
• 1003-29-8 2-pyrrole aldehyde 
• 180253-66-1 3-(tert-butyloxycarbonylamino)-4-methyl-pyridine 

Downstream Products

• 152955-67-4 N₆-benzyl-6-azaindole 
• 152955-66-3 N1-benzyl-6-azaindole 
• 67058-76-8 3-bromo-1H-pyrrolo[2,3-c]pyridine 
• 357263-51-5 methyl α-oxo-6-azaindole-3-acetate 
• 460053-59-2 3-benzoyl-6-azaindole 
• 67058-71-3 1-(1H-pyrrolo[2,3-c]pyridin-3-yl)ethanone 
• 1195996-55-4 6-methyl-1H-pyrrolo[2,3-c]pyridin-6-ium iodide 
• 271-34-1 3-iodo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[3,2-c]pyridine 
• 1253384-12-1 pyrrolo[2,3-c]pyridin-1-yl-acetic acid benzyl ester 
• 956003-24-0 3-iodo-1H-pyrrolo[2,3-c]pyridine 
• 1026723-10-3 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(pyrrolo[2,3-c]pyridin-1-ylmethyl)pentan-2-ol 
• 1316228-55-3 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-1H-pyrrolo[2,3-c]pyridine 
• 1174038-59-5 tert-butyl 3-iodo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate 
• 1316228-31-5 C₂₁H₂₁N₅O₂ 

Relevant academic research and scientific papers

COMPOUNDS FOR USING IN IMAGING AND PARTICULARLY FOR THE DIAGNOSIS OF NEURODEGENERATIVE DISEASES

The invention relates to compounds of formula (II) for using in imaging and particularly for the diagnosis of neurodegenerative diseases

Azaindolylsulfonamides, with a more selective inhibitory effect on histone deacetylase 6 activity, exhibit antitumor activity in colorectal cancer HCT116 cells

A series of indolylsulfonylcinnamic hydroxamates has been synthesized. Compound 12, (E)-3-(3-((1H-pyrrolo[2,3-b]pyridin-1-yl)sulfonyl)phenyl)-N- hydroxyacrylamide, which has a 7-azaindole core cap, was shown to have antiproliferative activity against KB, H460, PC3, HSC-3, HONE-1, A549, MCF-7, TSGH, MKN45, HT29, and HCT116 human cancer cell lines. Pharmacological studies indicated that 12 functions as a potent HDAC inhibitor with an IC50 value of 0.1 μM. It is highly selective for histone deacetylase 6 (HDAC6) and is 60-fold more active than against HDAC1 and 223-fold more active than against HDAC2. It has a good pharmacokinetic profile with oral bioavailability of 33%. In in vivo efficacy evaluations in colorectal HCT116 xenografts, compound 12 suppresses tumor growth more effectively than SAHA (1, N-hydroxy-N′- phenyloctanediamide) and is therefore seen as a suitable candidate for further investigation.

Novel 3-azaindolyl-4-arylmaleimides exhibiting potent antiangiogenic efficacy, protein kinase inhibition, and antiproliferative activity

Tumor growth and metastasis are highly associated with the overexpression of protein kinases (PKs) regulating cell growth, apoptosis resistance, and prolonged cell survival. This study describes novel azaindolyl-maleimides with significant inhibition of PKs, such as VEGFR, FLT-3, and GSK-3β which are related to carcinogenesis. Furthermore, these compounds exhibit high kinase selectivity and potent inhibition of angiogenesis and cell proliferation, offering versatile options in cancer treatment strategies.

Novel indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists: Design, synthesis, structure-activity relationships, physicochemical properties and biological activity

The discovery, synthesis and structure-activity relationship (SAR) of a novel series of cannabinoid 1 (CB1) and cannabinoid 2 (CB 2) receptor ligands are reported. Based on the aminoalkylindole class of cannabinoid receptor agonists, a biphenyl moiety was introduced as novel lipophilic indole 3-acyl substituent in 11-16. Furthermore, the 3-carbonyl tether was replaced with a carboxamide linker in 17-20 and the azaindole (pyrrolopyridine) nucleus was designed as indole bioisostere with improved physicochemical properties in 21-25. Through these SAR efforts, several high affinity CB1/CB2 dual cannabinoid receptor ligands were identified. Indole-3-carboxamide 17 displayed single-digit nanomolar affinity and ～80 fold selectivity for CB1 over the CB2 receptor. The azaindoles displayed substantially improved physicochemical properties (lipophilicity; aqueous solubility). Azaindole 21 elicited potent cannabinoid activity. Cannabinoid receptor agonists 17 and 21 potently modulated excitatory synaptic transmission in an acute rat brain slice model of cannabinoid receptor-modulated neurotransmission.

KINASE INHIBITORS AND THEIR USE AS PHARMACEUTICAL AGENTS

Described herein are compounds that are inhibitors of one or more protein kinases. Also described are pharmaceutical compositions and medicaments that include the compounds described herein. Also described herein are methods of using such protein kinase inhibitors, alone and in combination with other compounds, for conditions or diseases mediated or dependent upon protein kinases

KINASE INHIBITORS AND THEIR USE AS PHARMACEUTICAL AGENTS

Described herein are compounds that are inhibitors of one or more protein kinases. Also described are pharmaceutical compositions and medicaments that include the compounds described herein. Also described herein are methods of using such protein kinase inhibitors, alone and in combination with other compounds, for conditions or diseases mediated or dependent upon protein kinases.

NOVEL 6-AZAINDOLE AMINOPYRIMIDINE DERIVATIVES HAVING NIK INHIBITORY ACTIVITY

The present invention relates to a compound of formula I: wherein: R1 is C1-6 alkyl, C3-8 cycloalkyl, aryl, heterocyclyl, or -COR1x, where the C1-6 alkyl, C3-8 cycloalkyl, aryl, and heterocyclyl may be substituted; and R1x is C3-8 cycloalkyl, aryl, or heterocyclyl, any of which may be substituted; R2, R3, R4, R5, R6, and R7 are each independently hydrogen, halogen, C1-6 alkyl, or aryl, where the C1-6 alkyl or aryl may be substituted; R8 is hydrogen, C1-6 alkyl, aryl, or heterocyclyl, any of which may be substituted; or a pharmaceutically acceptable salt or ester thereof.

Site-selective azaindole arylation at the azine and azole rings via N-oxide activation

Subjection of N-methyl 6-and 7-azaindole N-oxides to a Pd(OAc) 2/DavePhos catalyst system enables regioselective direct arylation of the azine ring. Following deoxygenation, 7-azaindole substrates undergo an additional regioselective azole direct arylation event in good yield.

3-Amino-1-arylpropyl azaindoles and uses thereof

The present invention provides compounds of the formula: or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein p, Ar, R1, R2, R3, Ra, Rb, Rc, Rd and Re are defined herein. Also provided are pharmaceutical compositions, methods of using, and methods of preparing the compounds.

Azaindolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands

The present invention provides a compound of formula I and the use thereof for the therapeutic treatment of disorders relating to or affected by the 5-HT6 receptor.