817554-70-4

Basic information

• Product Name: 1-Pyrrolidinecarboxylicacid,2-(hydroxymethyl)-3-methyl-,1,1-dimethylethylester,(2S,3S)-(9CI)
• Synonyms: 1-Pyrrolidinecarboxylicacid,2-(hydroxymethyl)-3-methyl-,1,1-dimethylethylester,(2S,3S)-(9CI)
• CAS NO: 817554-70-4
• Molecular Formula: C₁₁H₂₁NO₃
• Molecular Weight: 0
• Product Categories: METHYL
• Mol File: 817554-70-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Pyrrolidinecarboxylicacid,2-(hydroxymethyl)-3-methyl-,1,1-dimethylethylester,(2S,3S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylicacid,2-(hydroxymethyl)-3-methyl-,1,1-dimethylethylester,(2S,3S)-(9CI)(817554-70-4)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylicacid,2-(hydroxymethyl)-3-methyl-,1,1-dimethylethylester,(2S,3S)-(9CI)(817554-70-4)

Safety Data

• Hazardous Substances Data: 817554-70-4(Hazardous Substances Data)

Upstream product

• 158038-37-0 (2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 10512-89-7 (2S,3S)-3-methylproline 
• 61406-66-4 (2S,3S)-1-(tert-butoxycarbonyl)-3-methylpyrrolidine-2-carboxylic acid 
• 411225-57-5 (2S,3S)-1-tert-butyl 2-ethyl 3-methyl-pyrrolidine-1,2-dicarboxylate 
• 138871-60-0 (4S,5S)-5-tert-butyldiphenylsilyloxymethyl-N-tert-butyloxycarbonyl-4-methylpyrrolidin-2-one 

Downstream Products

• 1283146-02-0 ((2S,3S)-3-methyl-1-(4-(2-methylbenzyl)phenyl)pyrrolidin-2-yl)methanol 
• 1283146-03-1 2-((2R,3S)-3-methyl-1-(4-(2-methylbenzyl)phenyl)pyrrolidin-2-yl)acetonitrile 
• 1283142-53-9 2-((2R,3S)-3-methyl-1-(4-(2-methylbenzyl)phenyl)pyrrolidin-2-yl)acetic acid trifluoroacetic acid salt 
• 10512-89-7 (2S,3S)-3-methylproline 

Relevant articles and documents

Discovery of Pyrrolidine-Containing GPR40 Agonists: Stereochemistry Effects a Change in Binding Mode

A novel series of pyrrolidine-containing GPR40 agonists is described as a potential treatment for type 2 diabetes. The initial pyrrolidine hit was modified by moving the position of the carboxylic acid, a key pharmacophore for GPR40. Addition of a 4-cis-CF3 to the pyrrolidine improves the human GPR40 binding Ki and agonist efficacy. After further optimization, the discovery of a minor enantiomeric impurity with agonist activity led to the finding that enantiomers (R,R)-68 and (S,S)-68 have differential effects on the radioligand used for the binding assay, with (R,R)-68 potentiating the radioligand and (S,S)-68 displacing the radioligand. Compound (R,R)-68 activates both Gq-coupled intracellular Ca2+ flux and Gs-coupled cAMP accumulation. This signaling bias results in a dual mechanism of action for compound (R,R)-68, demonstrating glucose-dependent insulin and GLP-1 secretion in vitro. In vivo, compound (R,R)-68 significantly lowers plasma glucose levels in mice during an oral glucose challenge, encouraging further development of the series.

GUANIDINO-SUBSTITUTED QUINAZOLINONE COMPOUNDS AS MC4-R AGONISTS

A variety of small molecule, guanidine-containing molecules capable of acting as MC4-R agonists are provided. The compounds are useful in treating MC4-R mediated diseases when administered to subjects. The compounds have the structure IA, IB, and IC where the values of the variables are defined herein.