221675-35-0

Usage

Uses

Used in Organic Synthesis:
1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows for versatile chemical reactions, facilitating the creation of a wide range of compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester is utilized as a building block in the development of new drugs. Its potential role in medicinal chemistry includes the synthesis of bioactive molecules that could target specific diseases or conditions, contributing to the advancement of therapeutic agents.
Used in Medicinal Chemistry:
1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester is employed as a structural component in the design and synthesis of novel pharmaceutical compounds. Its presence in these molecules can influence their pharmacological properties, such as potency, selectivity, and bioavailability, making it a valuable asset in the discovery of new drugs.
Used in Drug Development:
In the process of drug development, 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester serves as a precursor in the synthesis of potential drug candidates. Its reactivity and structural features are harnessed to create molecules with desired therapeutic effects, undergoing rigorous testing and optimization to advance towards clinical applications.

InChI:InChI=1/C10H10N2O2/c1-2-14-10(13)8-6-7-4-3-5-11-9(7)12-8/h3-6H,2H2,1H3,(H,11,12)

Upstream product

• 109-04-6 2-bromo-pyridine 
• 128071-75-0 2-bromopyridine-3-carboxaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 108-99-6 3-Methylpyridine 
• 64-17-5 ethanol 
• 136818-50-3 7-azaindole-2-carboxylic acid 
• 1205747-95-0 Ethyl 3-{2-[(tert-butoxycarbonyl)amino]-3-pyridyl}-2-oxopropanoate 
• 1603-40-3 3-methylpyridin-2-ylamine 
• 138343-75-6 tert-butyl (3-methylpyridin-2-yl)carbamate 
• 143141-23-5 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine 
• 189089-90-5 1-(phenyl-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid 
• 271-63-6 7-Azaindole 
• 2999-46-4 Ethyl isocyanoacetate 
• 287384-79-6 1-(tert-butyl) 2-ethyl 2-hydroxy-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1,2-dicarboxylate 

Downstream Products

• 920978-89-8 ethyl 1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylate 
• 172648-34-9 ethyl 1-methyl-7-azaindole-2-carboxylate 
• 1198416-38-4 C₁₀H₁₀N₂O₂ 
• 1272003-73-2 C₁₅H₉N₃O₂ 
• 1407189-77-8 C₁₉H₁₈F₃N₃O₂ 
• 1234616-71-7 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid 
• 942920-55-0 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester 
• 1352805-43-6 N-methoxy-N-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxamide 
• 136818-50-3 7-azaindole-2-carboxylic acid 
• 287384-82-1 ethyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate-7-oxide 

Relevant academic research and scientific papers

Substituted indoles as selective protease activated receptor 4 (PAR-4) antagonists: Discovery and SAR of ML354

Herein we report the discovery and SAR of an indole-based protease activated receptor-4 (PAR-4) antagonist scaffold derived from a similarity search of the Vanderbilt HTS collection, leading to MLPCN probe ML354 (VU0099704). Using a novel PAC-1 fluorescent αIIbβ3 activation assay this probe molecule antagonist was found to have an IC50of 140 nM for PAR-4 with 71-fold selectivity versus PAR-1 (PAR-1IC50= 10 μM).

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.

HETEROCYCLIC COMPOUNDS AS PAD INHIBITORS

Heterocyclic compounds of Formula (I), (II), and (III) are described herein along with their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof. The compounds described herein, their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosis, cutaneous lupus erythematosis, ulcerative colitis, cancer, cystic fibrosis, asthma, multiple sclerosis and psoriasis.

IMIDAZO-PYRIDINE COMPOUNDS AS PAD INHIBITORS

Heterocyclic compounds of Formula (I), (II), and (III) are described herein along with their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof. The compounds described herein, their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosis, cutaneous lupus erythematosis, ulcerative colitis, cancer, cystic fibrosis, asthma, multiple sclerosis and psoriasis. The process of preparation of the compounds of Formula (I), (II), and (III), their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof, along with a pharmaceutical composition comprising a compound of Formula (I), Formula (II), Formula (III), or a pharmaceutically acceptable salt thereof have also been described.

Synthesis, biological evaluation and molecular modeling of a novel series of 7-azaindole based tri-heterocyclic compounds as potent CDK2/Cyclin E inhibitors

From four molecules, inspired by the structural features of fascaplysin, with an interesting potential to inhibit cyclin-dependent kinases (CDKs), we designed a new series of tri-heterocyclic derivatives based on 1H-pyrrolo[2,3-b]pyridine (7-azaindole) an

ANTI-HER2 ANTIBODY-MAYTANSINE CONJUGATES AND METHODS OF USE THEREOF

The present disclosure provides anti-HER2 antibody-maytansine conjugate structures. The disclosure also encompasses methods of production of such conjugates, as well as methods of using the same.

Exploring the effects of linker composition on site-specifically modified antibody-drug conjugates

In the context of antibody-drug conjugates (ADCs), noncleavable linkers provide a means to deliver cytotoxic small molecules to cell targets while reducing systemic toxicity caused by nontargeted release of the free drug. Additionally, noncleavable linker

LRRK2 INHIBITORS

Provided herein are compounds that inhibit or partially inhibit the activity of leucine rich repeat kinases. Also provided herein are methods of treatment of CNS disorders comprising administration of inhibitors of leucine rich repeat kinases.

Discovery of novel pyrrolopyridazine scaffolds as transient receptor potential vanilloid (TRPV1) antagonists

A novel indolizine class of compounds was identified as TRPV1 antagonist from an HTS campaign. However, this indolizine class proved to be unstable and reacted readily with glutathione when exposed to light and oxygen. Reactivity was reduced by the introduction of a nitrogen atom alpha to the indolizine nitrogen. The pyrrolopyridazine core obtained proved to be inert to the action of light and oxygen. The synthesis route followed the one used for the indolizine compounds, and the potency and ADMET profile proved to be similar.

Design, synthesis and biological evaluation of new thalidomide analogues as TNF-α and IL-6 production inhibitors

Several thalidomide analogues were synthesized and compared to thalidomide and its more active analogue, lenalidomide, for their ability to inhibit the production of the pro-inflammatory cytokine tumour necrosis factor (TNF)-α and interleukin (IL)-6 by LPS-activated peripheral blood mononuclear cells (PBMCs). Among these compounds, two analogues containing sulfonyl group displayed interesting downregulation of TNF-α and IL-6 production.