1026841-49-5

Basic information

• Product Name: 3-phenylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• Synonyms: 3-phenylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS NO: 1026841-49-5
• Molecular Weight: 276.379
• Mol File: 1026841-49-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-phenylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester(1026841-49-5)
• EPA Substance Registry System: 3-phenylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester(1026841-49-5)

Safety Data

• Hazardous Substances Data: 1026841-49-5(Hazardous Substances Data)

Upstream product

• 138108-72-2 tert-butyl (R)-3-hydroxymethylpyrrolidine-1-carboxylate 
• 99735-47-4 (3R)-1-[(R)-1-phenylethyl]-3-(hydroxymethyl)pyrrolidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 62-53-3 aniline 
• 177947-76-1 (3R)-1-(tert-butoxycarbonyl)-3-[(methane-sulfonyloxy)methyl]pyrrolidine 

Relevant articles and documents

Synthesis and serotonergic activity of 3-[2-(pyrrolidin-1- yl)ethyl]indoles: Potent agonists for the h5-HT(1D) receptor with high selectivity over the h5-HT(1B) receptor

The design, synthesis, and biological evaluation of a novel series of 3- [2-(pyrrolidin-1-yl)ethyl]-indoles with excellent selectivity for h5-HT(1D) (formerly 5-HT(1Dα)) receptors over h5-HT(1B) (formerly 5-HT(1Dβ)) receptors are described. Clinically effective antimigraine drugs such as Sumatriptan show little selectivity between h5-HT(1D) and h5-HT(1B) receptors. The differential expression of h5-HT(1D) and h5-HT(1B) receptors in neural and vascular tissue prompted an investigation of whether a compound selective for the h5-HT(1D) subtype would have the same clinical efficacy but with reduced side effects. The pyrrolidine 3b was initially identified as having 9-fold selectivity for h5-HT(1D) over h5-HT(1B) receptors. Substitution of the pyrrolidine ring of 3b with methylbenzylamine groups gave compounds with nanomolar affinity for the h5-HT(1D) receptor and 100-fold selectivity with respect to h5-HT(1B) receptors. Modification of the indole 5-substituent led to the oxazolidinones 24a,b with up to 163-fold selectivity for the h5-HT(1D) subtype and improved selectivity over other serotonin receptors. The compounds were shown to be full agonists by measurement of agonist-induced [35S]GTPγS binding in CHO cells expressed with h5-HT receptors. This study suggests that the h5-HT(1D) and h5-HT(1B) receptors can be differentiated by appropriate substitution of the ligand in the region which binds to the aspartate residue and reveals a large binding pocket in the h5-HT(1D) receptor domain which is absent for the h5-HT(1B) receptor. The compounds described herein will be important tools to delineate the role of h5-HT(1D) receptors in migraine.