37033-95-7

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATE is used as a reactant for the preparation of indolyl ethanones, which serve as indoleamine 2,3-dioxygenase inhibitors. These inhibitors play a crucial role in modulating the activity of the enzyme indoleamine 2,3-dioxygenase, which is involved in the metabolism of tryptophan and has been linked to various physiological and pathological processes.
ETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATE is also used as a reactant for the preparation of histamine H3 receptor inverse agonists. These compounds have the potential to modulate the activity of histamine H3 receptors, which are involved in various physiological processes, including the regulation of wakefulness, appetite, and cognitive function. Inverse agonists of the histamine H3 receptor may have therapeutic applications in the treatment of conditions such as insomnia, obesity, and cognitive disorders.
In addition, ETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATE is used as a reactant for the preparation of PPAR-γ binding agents. These agents have the potential to modulate the activity of the peroxisome proliferator-activated receptor gamma (PPAR-γ), a nuclear receptor that plays a key role in the regulation of lipid metabolism and glucose homeostasis. PPAR-γ binding agents may have applications in the treatment of metabolic disorders, such as type 2 diabetes and obesity, as well as in the development of therapies for osteoporosis.
Furthermore, ETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATE is used as a reactant for the preparation of nonpeptide glycoprotein IIB/IIIA inhibitors. These inhibitors target the glycoprotein IIB/IIIA receptor, which is involved in platelet aggregation and blood clot formation. Nonpeptide glycoprotein IIB/IIIA inhibitors may have therapeutic applications in the prevention and treatment of thrombotic disorders, such as acute coronary syndrome and stroke.
Used in Chemical Industry:
In the chemical industry, ETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATE may be used as an intermediate or building block in the synthesis of various complex organic compounds, particularly those with potential applications in the pharmaceutical, agrochemical, and materials science sectors. Its unique structural features and reactivity make it a valuable component in the development of novel molecules with diverse biological activities and properties.

InChI:InChI=1/C18H17NO3/c1-2-21-18(20)17-11-14-10-15(8-9-16(14)19-17)22-12-13-6-4-3-5-7-13/h3-11,19H,2,12H2,1H3

Upstream product

• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 55974-70-4 1-(4-(benzyloxy)phenyl)hydrazine hydrochloride 
• 52068-30-1 4-benzyloxyphenylhydrazine hydrochloride 
• 100-39-0 benzyl bromide 
• 24985-85-1 ethyl 5-hydroxyindole-2-carboxylate 
• 4382-54-1 5-methoxy-1H-indole-2-carboxylic acid 
• 21598-06-1 5-hydroxyindole-2-carboxylic acid 

Downstream Products

• 197841-22-8 ethyl-1-(6-chloro-3,4-methylenedioxybenzyl)-5-(benzyloxy)indolecarboxylate 
• 173844-27-4 N-methyl-N-phenethyl-2-(5-benzyloxy-2-carboxyindol-1-yl)acetamide 
• 167631-20-1 5-benzyloxy-3-iodo-1H-indole-2-carboxylic acid ethyl ester 
• 902757-08-8 5-benzyloxy-1-(4-methyl-3-nitrophenyl)indole-2-carboxylic acid ethyl ester 
• 902169-36-2 5-benzyloxy-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester 
• 158072-98-1 ethyl 5-(benzyloxy)-3-bromo-1H-indole-2-carboxylate 
• 241489-76-9 5-(Benzyloxy)-1-(4-{[3,5-bis(trifluoromethyl)phenoxy]methyl}benzyl)-1H-indole-2-carboxylic Acid 
• 197841-36-4 ethyl 5-benzyloxy-1-(2-chloro-4,5-methylenedioxybenzyl)indole-2-carboxylate 
• 1246923-92-1 ethyl 5-benzyloxy-1-(4-methoxyphenyl)indol-2-ylcarboxylate 
• 1278518-33-4 1-(5-benzyloxy-1H-indol-2-yl)-2-(pyridin-3-yl)-ethan-1-one 
• 1215119-17-7 ethyl 5-(benzyloxy)-1-(4-ethoxy-4-oxobutyl)-1H-indole-2-carboxylate 
• 1215118-15-2 (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl) benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid 
• 1215118-31-2 2-(7-(4-chloro-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid 
• 1215118-66-3 tert-butyl 2-(7-(3-cyano-5-(trifluoromethoxy)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate 

Relevant academic research and scientific papers

AROMATIC RING DERIVATIVE AS IMMUNOREGULATION AND PREPARATION METHOD AND APPLICATION OF AROMATIC RING DERIVATIVE

Relating to a compound represented by formula (I) and a pharmaceutically acceptable salt of the compound, and an application of the compound as an S1P1 agonist.

Synthesis method of indole-2-carboxylic acid and derivative thereof

The invention relates to a synthesis method of indole-2-carboxylic acid and a derivative thereof, belonging to the field of organic synthesis. In the synthesis method, the indole-2-carboxylic acid isprepared through two steps of reaction with phenylhydrazine hydrochloride and ethyl pyruvate as raw materials and sulfuric acid as a catalyst. The synthesis method has a short process and uses fewer raw materials, the total yield of indole-2-carboxylic acid reaches 70% or above. The method can synthesize both indole-2-carboxylic acid and the derivative thereof, thereby being suitable for industrial production.

(7-Benzyloxy-2,3-dihydro- 1H -pyrrolo[1,2-a]indol-1-yl)acetic acids as S1P1 functional antagonists

S1P1 is a validated target for treatment of autoimmune disease, and functional antagonists with superior safety and pharmacokinetic properties are being sought as second generation therapeutics. We describe the discovery and optimization of (7-benzyloxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acids as potent, centrally available, direct acting S1P1 functional antagonists, with favorable pharmacokinetic and safety properties.

Complementary asymmetric routes to (R)-2-(7-hydroxy-2,3-dihydro-1 H-pyrrolo[1,2-a]indol-1-yl)acetate

Two distinct and scalable enantioselective approaches to the tricyclic indole (R)-2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate, an important synthon for a preclinical S1P1 receptor agonist, are reported. Route 1 employs a modified version of Smith's modular 2-substituted indole synthesis as the key transformation. Route 2 involves a highly enantioselective CuH-catalyzed 1,4-hydrosilylation as the stereodefining step. Both routes can be performed without chromatography to provide multigram quantities of the tricycle in ≥98% ee.

PROCESSES FOR THE PREPARATION OF S1P1 RECEPTOR MODULATORS AND CRYSTALLINE FORMS THEREOF

The present invention relates to salts, processes, and process intermediates useful in the preparation of (R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid of Formula (Ia), salts, and crystalline forms thereof. The compound (R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid has been identified as an S1P1 receptor modulator that is useful in the treatment of S1P1 receptor-associated disorders, for example, diseases and disorders mediated by lymphocytes, transplant rejection, autoimmune diseases and disorders, inflammatory diseases and disorders (e.g., acute and chronic inflammatory conditions), cancer, and conditions characterized by an underlying defect in vascular integrity or that are associated with angiogenesis such as may be pathologic (e.g., as may occur in inflammation, tumor development, and atherosclerosis).