155135-61-8

Basic information

• Product Name: 2,3-DIHYDRO-1H-INDOLE-4-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE
• Synonyms: 2,3-DIHYDRO-1H-INDOLE-4-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE;Methyl 2,3-dihydro-1H-indole-4-carboxylate;Methyl indoline-4-carboxylate;4-Methoxycarbonyl-2,3-dihydro-1h-indole;1H-Indole-4-carboxylic acid, 2,3-dihydro-, Methyl ester;2,3-DIHYDRO-1H-INDOLE-4-CARBOXYLIC ACID METHYL
• CAS NO: 155135-61-8
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 213.66078
• Mol File: 155135-61-8.mol

Chemical Properties

• Boiling Point: 328℃
• Flash Point: 152℃
• Appearance: /
• Density: 1.162
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 2,3-DIHYDRO-1H-INDOLE-4-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIHYDRO-1H-INDOLE-4-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE(155135-61-8)
• EPA Substance Registry System: 2,3-DIHYDRO-1H-INDOLE-4-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE(155135-61-8)

Safety Data

• Hazardous Substances Data: 155135-61-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-DIHYDRO-1H-INDOLE-4-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE is used as a reagent for the preparation of indolinylhydroxyureas and hydroxamic acids. These compounds are known for their potential as allergy and inflammation inhibitors, making them valuable in the development of new medications for treating various conditions related to inflammation and allergic responses.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,3-DIHYDRO-1H-INDOLE-4-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE can be utilized as a building block or intermediate for the synthesis of more complex organic molecules. Its unique structure and functional groups make it a versatile compound for creating a wide range of chemical products, including pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

• 39830-66-5 methyl 1H-indole-4-carboxylate 

Downstream Products

• 2624131-45-7 1-(6-(3-fluoro-5-(trifluoromethyl)benzyl)pyrimidin-4-yl)-N-(2-hydroxyethyl)indoline-4-carboxamide 
• 905274-11-5 indolin-4-ylmethanol 
• 1428130-14-6 methyl 1-(5-chloro-2-((2,4-difluorobenzyl)oxy)benzyl)indoline-4-carboxylate 
• 1427422-51-2 1-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)indoline-4-carboxylic acid 
• 1427423-22-0 methyl 1-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)indoline-4-carboxylate 

Relevant articles and documents

Indole Chloropyridinyl Ester-Derived SARS-CoV-2 3CLpro Inhibitors: Enzyme Inhibition, Antiviral Efficacy, Structure-Activity Relationship, and X-ray Structural Studies

Here, we report the synthesis, structure-activity relationship studies, enzyme inhibition, antiviral activity, and X-ray crystallographic studies of 5-chloropyridinyl indole carboxylate derivatives as a potent class of SARS-CoV-2 chymotrypsin-like protease inhibitors. Compound 1 exhibited a SARS-CoV-2 3CLpro inhibitory IC50 value of 250 nM and an antiviral EC50 value of 2.8 μM in VeroE6 cells. Remdesivir, an RNA-dependent RNA polymerase inhibitor, showed an antiviral EC50 value of 1.2 μM in the same assay. Compound 1 showed comparable antiviral activity with remdesivir in immunocytochemistry assays. Compound 7d with an N-allyl derivative showed the most potent enzyme inhibitory IC50 value of 73 nM. To obtain molecular insight into the binding properties of these molecules, X-ray crystal structures of compounds 2, 7b, and 9d-bound to SARS-CoV 3CLpro were determined, and their binding properties were compared.

Discovery of Potent and Brain-Penetrant GPR52 Agonist that Suppresses Psychostimulant Behavior

The G protein-coupled receptor 52 (GPR52) is an orphan receptor that is selectively expressed in the striatum and regulates various brain functions through activation of cAMP-dependent pathways. GPR52 has been identified as a promising therapeutic target for central nervous system disorders including schizophrenia and substance use disorders. Here, a series of novel GPR52 agonists were designed, synthesized, and evaluated based on compound 4. Several potent and efficacious GPR52 agonists (12c, 23a, 23d, 23e, 23f, and 23h) were identified with nanomolar range potency based on a systematic structure-activity relationship exploration. Further studies of 12c indicate enhanced efficacy, excellent target selectivity, and pharmacokinetic properties including good brain permeability. In vivo proof-of-concept investigations revealed that 12c displayed antipsychotic-like activity by significantly inhibiting amphetamine-induced hyperlocomotor behavior in mice. Collectively, our findings have resulted in an efficacious, brain-penetrant GPR52 agonist as a valuable pharmacological tool for investigating the physiological and therapeutic potential of GPR52 activation.

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