156270-06-3

Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid is used as a reactant for the synthesis of azaindol derivatives, which are considered as new acrosin inhibitors. Acrosin inhibitors have potential applications in the development of contraceptives and treatments for male infertility. The compound is also used for the preparation of triazoles via regioselective heterocyclization reactions, which can lead to the creation of new pharmaceutical compounds with various therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid serves as a reactant for the synthesis of azaindolylcarboxy-endo-tropanamide. 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid can be further utilized in the development of novel chemical entities with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C8H6N2O2/c11-8(12)6-4-10-7-5(6)2-1-3-9-7/h1-4H,(H,9,10)(H,11,12)

Upstream product

• 271-63-6 7-Azaindole 
• 108-24-7 acetic anhydride 
• 4649-09-6 1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde 
• 269726-49-0 2-amino-1-tert-butyl-4-cyanopyrrole 
• 4414-89-5 1H-pyrrolo[2,3-b]pyridine-3-carbonitrile 
• 269726-48-9 N-tert-butylaminomethylenesuccinonitrile 
• 269726-50-3 1-tert-butyl-3-cyano-7-azaindole 
• 76-02-8 trifluoroacetyl chloride 
• 1065100-83-5 (1H-pyrrolo[2,3-b]pyridin-3-yl)methanol 
• 163220-69-7 2,2,2-trichloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone 

Downstream Products

• 808137-94-2 1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester 
• 1263816-09-6 3-(3-isopropyl-1-(4-methoxyphenyl)-1H-1,2,4-triazol-5-yl)-1H-pyrrolo[2,3-b]pyridine 
• 310887-39-9 1H-pyrrolo[2,3-b]pyridine-3-carbohydrazide 
• 1210437-54-9 phenyl-[5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1,3,4-oxadiazol-2-yl]amine 
• 1210437-67-4 1-(1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-4-phenylthiosemicarbazide 
• 1210437-79-8 C₁₇H₁₇N₅O₂S 
• 1273122-75-0 C₁₇H₁₄N₂O₃ 
• 1273122-77-2 C₁₇H₁₃FN₂O₃ 
• 1273122-79-4 C₁₇H₁₃FN₂O₃ 
• 1273122-81-8 C₁₇H₁₃ClN₂O₃ 
• 1273122-83-0 C₁₈H₁₆N₂O₃ 
• 1273122-85-2 C₁₈H₁₆N₂O₄ 
• 1273122-87-4 C₁₉H₁₈N₂O₅ 
• 1273122-89-6 C₁₇H₁₂Cl₂N₂O₃ 

Relevant academic research and scientific papers

A practical synthesis of 7-azaindolylcarboxy-endo-tropanamide (DF 1012)

An optimised cost-effective synthesis of the new antitussive drug, DF1012, is herewith reported. The new synthetic route to the key intermediate DF1005 is based on the unusual deprotection step of the 1-tert-butyl-3-cyano-7-azaindole intermediate, which can also be regarded as a convenient way for the industrial production of the expensive 7-azaindole 1. The second key intermediate, endo-tropanamine 6, was obtained in high yield by a novel one-pot stereoselective process using a Pd-catalysed reductive amination procedure.

Strategies to develop selective CB2 receptor agonists from indole carboxamide synthetic cannabinoids

Activation of the CB2 receptor is an attractive therapeutic strategy for the treatment of a wide range of inflammatory diseases. However, receptor subtype selectivity is necessary in order to circumvent the psychoactive effects associated with activation of the CB1 receptor. We aimed to use potent, non-selective synthetic cannabinoids designer drugs to develop selective CB2 receptor agonists. Simple structural modifications such as moving the amide substituent of 3-amidoalkylindole synthetic cannabinoids to the 2-position and bioisosteric replacement of the indole core to the 7-azaindole scaffold are shown to be effective and general strategies to impart receptor subtype selectivity. 2-Amidoalkylindole 16 (EC50 CB1 > 10 μM, EC50 CB2 = 189 nM) and 3-amidoalkyl-7-azaindole 21 (EC50 CB1 > 10 μM, EC50 = 49 nM) were found to be potent and selective agonists with favourable physicochemical properties. Docking studies were used to elucidate the molecular basis for the observed receptor subtype selectivity for these compounds.

Synthesis method of 7-azaindole-3-carboxylic acid

The invention discloses a synthesis method of 7-azaindole-3-carboxylic acid. The synthesis method of the 7-azaindole-3-carboxylic acid comprises the following steps of adding 7-azaindole and water into a reaction kettle, stirring for 20 to 45min, then adding tetramethyl guanidine and zeolite, heating to 50 to 70 DEG C, adding formaldehyde after uniformly stirring and mixing, carrying out microwaveirradiation for 1 to 2h after uniformly stirring, then continuously stirring for reacting for 6 to 8h, filtering, dissolving a precipitate into dichloromethane, filtering again, carrying out vacuum distillation on a filter liquor, and recrystallizing to obtain 7-azaindole-3-methyl alcohol; oxidizing the 7-azaindole-3-methyl alcohol to obtain the 7-azaindole-3-carboxylic acid. The synthesis methodprovided by the invention is simple to operate, mild in conditions, less in byproducts, high in product purity, and higher in product yield.

Acrosin structure-based design, synthesis and biological activities of 7-azaindol derivatives as new acrosin inhibitors

A series of 7-azaindol derivatives were designed based on the homologous 3D model of human acrosin. These compounds were synthesized and evaluated for their human acrosin inhibitory activities in vitro. Compounds 7a, 7i, 7j, 7k and 7n showed highly inhibitory activity against human acrosin. The three-dimensional structure-activity relationship was investigated through a CoMFA model, which provided valuable information to further study of potential human acrosin inhibitors.

PYRIDINONYL PDK1 INHIBITORS

The present invention provides pyridinonyl PDKl inhibitors and methods of treating cancer using the same.

AZAINDOLE CARBOXAMIDES

The invention relates to azaindole derivatives of general formula (I), wherein X represents a group of general formula (X1). Said compounds have a therapeutic potential in the treatment of diseases that are accompanied by an impaired dopamine metabolism a

3-(GUANIDINOCARBONYL)HETEROCYCLE DERIVATIVES, PREPARATION PROCESS AND INTERMEDIATES OF THIS PROCESS, THEIR USE AS MEDICAMENTS, AND PHARMACEUTICAL COMPOSITIONS INCLUDING THEM

The present invention relates to the novel compounds of the formula (I) and their pharmaceutically acceptable salts. The inventive compounds are suitable, for example, as antiarrhythmic medicaments with a cardioprotective component for infarction prophyla