1260606-90-3

Basic information

• Product Name: (2R,4R)-4-BENZYL-PYRROLIDINE-2-CARBOXYLIC ACID
• Synonyms: (4R)-4-BENZYL-D-PROLINE;(2R,4R)-4-BENZYL-PYRROLIDINE-2-CARBOXYLIC ACID
• CAS NO: 1260606-90-3
• Molecular Formula: C12H15NO2
• Molecular Weight: 205.25
• Mol File: 1260606-90-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R,4R)-4-BENZYL-PYRROLIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-4-BENZYL-PYRROLIDINE-2-CARBOXYLIC ACID(1260606-90-3)
• EPA Substance Registry System: (2R,4R)-4-BENZYL-PYRROLIDINE-2-CARBOXYLIC ACID(1260606-90-3)

Safety Data

• Hazardous Substances Data: 1260606-90-3(Hazardous Substances Data)

Usage

Description

(2R,4R)-4-BENZYL-PYRROLIDINE-2-CARBOXYLIC ACID is a chiral chemical compound belonging to the class of pyrrolidine carboxylic acids. It has a molecular formula of C13H17NO2 and a molecular weight of 219.28 g/mol. (2R,4R)-4-BENZYL-PYRROLIDINE-2-CARBOXYLIC ACID features two stereocenters, existing as a pair of enantiomers, with the (2R,4R) configuration being one of the possible configurations. The presence of a benzyl group attached to the pyrrolidine ring gives it a distinctive structure and chemical properties. Due to its unique characteristics, (2R,4R)-4-BENZYL-PYRROLIDINE-2-CARBOXYLIC ACID may have potential applications in various fields such as pharmaceuticals and organic synthesis.

Uses

Used in Pharmaceutical Industry:
(2R,4R)-4-BENZYL-PYRROLIDINE-2-CARBOXYLIC ACID is used as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable component in the development of new drugs with specific therapeutic effects.
Used in Organic Synthesis:
(2R,4R)-4-BENZYL-PYRROLIDINE-2-CARBOXYLIC ACID is used as an intermediate in organic synthesis for the production of other complex organic molecules. Its versatility and reactivity in chemical reactions contribute to the creation of a wide range of chemical products.

Upstream product

• 127949-74-0 (2S,4R)-4-(benzyl)di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate 
• 35418-16-7 L-t-butyl pyroglutamate 
• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 
• 1356352-02-7 C₂₁H₃₁NO₄ 
• 114029-41-3 N-carbobenzyloxy-4-(phenylmethylene)-L-proline 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 81653-75-0 N-(benzyloxycarbonyl)-4-(phenylmethylidene)-L-proline 

Downstream Products

• 153074-95-4 (2S,4R)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 

Relevant articles and documents

Discovery of a novel class of potent and orally bioavailable sphingosine 1-phosphate receptor 1 antagonists

A series of subtype selective sphingosine 1-phosphate receptor 1 (S1P 1) antagonists are disclosed. Our high-throughput screening campaign revealed hit 1 for which an increase in potency and mouse oral exposure was achieved with minor modifications to the chemical scaffold. In vivo efficacy revealed that at high doses compounds 12 and 15 inhibited tumor growth. Further optimization of our lead series led to the discovery of proline derivatives 37 (XL541) and 38 which had similar efficacy as our first generation analogues at significantly lower doses. Analogue 37 displayed excellent pharmacokinetics and oral exposure in multiple species.

Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines

Analogues of captopril, enalaprilat, and the phosphinic acid [[hydroxy(4-phenylbutyl)phosphinyl]acetyl)-L-proline incorporating 4-substituted proline derivatives have been synthesized and evaluated as inhibitors of angiotensin-converting enzyme (ACE) in vitro and in vivo. The 4-substituted prolines, incorporating alkyl, aryl, alkoxy, aryloxy, alkylthio, and arylthio substituents were prepared from derivatives of 4-hydroxy- and 4-ketoproline. In general, analogues of all three classes of inhibitors with hydrophobic substituents on proline were more potent in vitro than the corresponding unsubstituted proline compounds. 4-Substituted analogues of captopril showed greater potency and duration of action than the parent compound as inhibitors of the angiotensin I induced pressor response in normotensive rats. The S-benzoyl derivative of cis-4-(phenylthio)captopril, zofenopril, was found to be one of the most potent compounds of this class and is now being evaluated clinically as an antihypertensive agent. In the phosphinic acid series, the 4-ethylenethioketal and trans-4-cyclohexyl derivatives were found to be the most potent compounds in vitro and in vivo. A prodrug of the latter compound, fosinopril, is also being evaluated in clinical trials.

AMINO AND SUBSTITUTED AMINO PHOSPHINYL-ALKANOYL COMPOUNDS

Compounds of the formula STR1 wherein X is an imino acid or ester and R 1 is hydrogen, STR2 are useful hypotensive agents due to their angiotensin converting enzyme inhibition activity.