202932-18-1

Basic information

• Product Name: 3-Chlorocarbonylmethyl-indole-1-carboxylic acid benzyl ester
• Synonyms: 3-Chlorocarbonylmethyl-indole-1-carboxylic acid benzyl ester
• CAS NO: 202932-18-1
• Molecular Weight: 327.767
• Mol File: 202932-18-1.mol

Chemical Properties

• CAS DataBase Reference: 3-Chlorocarbonylmethyl-indole-1-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chlorocarbonylmethyl-indole-1-carboxylic acid benzyl ester(202932-18-1)
• EPA Substance Registry System: 3-Chlorocarbonylmethyl-indole-1-carboxylic acid benzyl ester(202932-18-1)

Safety Data

• Hazardous Substances Data: 202932-18-1(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 187244-70-8 1-(benzyloxycarbonyl)indol-3-yl acetic acid 
• 87-51-4 indole-3-acetic acid 

Downstream Products

• 202932-16-9 (4S,5R)-3-(1-benzyloxycarbonylindol-3-yl)acetyl-4-methyl-5-phenyl-1,3-oxazolidin-2-one 
• 919295-74-2 3-(3-diazo-2-oxo-propyl)-indole-1-carboxylic acid benzyl ester 
• 202932-23-8 3-[(S)-1-tert-Butoxycarbonylmethyl-2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-2-oxo-ethyl]-indole-1-carboxylic acid benzyl ester 
• 202932-28-3 3-[(R)-1-(Benzyloxycarbonylamino-methyl)-2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-2-oxo-ethyl]-indole-1-carboxylic acid benzyl ester 
• 851547-84-7 benzyl 3-(3-acetoxy-2-oxopropyl)-1H-indole-1-carboxylate 
• 851547-83-6 benzyl 3-(3-chloro-2-oxopropyl)-1H-indole-1-carboxylate 

Relevant articles and documents

2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[H] quinoline-4-carboxylic acid (PSI-697): Identification of a clinical candidate from the quinoline salicylic acid series of P-selectin antagonists

P-selectin-PSGL-1 interaction causes rolling of leukocytes on the endothelial cell surface, which subsequently leads to firm adherence and leukocyte transmigration through the vessel wall into the surrounding tissues. P-selectin is upregulated on the surface of both platelets and endothelium in a variety of atherosclerosis-associated conditions. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of atherosclerosis. High-throughput screening and subsequent analoging had led to the identification of compound 1 as the lead candidate. Herein, we report the continuation of this work and the discovery of a second-generation series, the tetrahydrobenzoquinoline salicylic acids. These compounds have improved pharmacokinetic properties, and a number of them have shown oral efficacy in mouse and rat models of atherogenesis and vascular injury. The lead 31 (PSI-697), is currently in clinical development for the treatment of atherothrombotic vascular events.

Methods and compositions for selectin inhibition

The present invention relates to the field of anti-inflammatory substances, and more particularly to novel compounds that act as antagonists of the mammalian adhesion proteins known as selectins. In some embodiments, methods for treating selectin mediated disorders are provided which include administration of compound of Formula I: wherein the constituent variables are defined herein.

Enantioselective synthesis of 2-substituted 3-aminopropanoic acid (β-alanine) derivatives which are β-analogues of aromatic amino acids

3-Aminopropanoic acid derivatives with a phenyl, 4-hydroxyphenyl, benzyl or indol-3-yl substituent at C-2 can be prepared enantioselectively by routes involving electrophilic attack of synthetic equivalents of [H2NCH2]+ upon enolates derived from chiral 3-acyl-1,3-oxazolidin-2-ones. tert-Butyl bromoacetate may be used as the electrophile, with subsequent introduction of nitrogen through the Curtius reaction, using the sequence of reagents (i) CF3CO2H; (ii) (PhO)2P(O)N3, Et3N, PhCH2OH; alternatively, direct electrophilic reaction with 1-[N-(benzyloxycarbonyl)aminomethyl]benzotriazole 4c or benzyl N-(acetoxymechyl)carbamate 2d introduces a protected aminomethyl group in a single step.