122536-73-6

Basic information

• Product Name: (R)-3-AMINO-1-CBZ-PYRROLIDINE
• Synonyms: (R)-BENZYL-3-AMINOPYRROLIDINE-1-CARBOXYLATE;(R)-(-)-1-CBZ-3-AMINOPYRROLIDINE;(R)-1-BENZYLOXYCARBONYL-3-AMINOPYRROLIDINE;(R)-3-AMINO-1-N-CBZ-PYRROLIDINE;(R)-3-AMINO-1-CBZ-PYRROLIDINE;(R)-3-AMINO-PYRROLIDINE-1-CARBOXYLIC ACID BENZYL ESTER;(R)-1-N-Cbz-3-Aminopyrrolidine HCl;(3R)-1-N-Cbz-3-Aminopyrrolidine
• CAS NO: 122536-73-6
• Molecular Formula: C₁₂H₁₆N₂O₂
• Molecular Weight: 220.27
• Mol File: 122536-73-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 310-316℃
• Boiling Point: 315 °C
• Flash Point: >230 °F
• Appearance: /
• Density: 1.155 g/mL at 25 °C
• Vapor Pressure: 3.37E-06mmHg at 25°C
• Refractive Index: n20/D 1.548
• Sensitive: Air Sensitive
• CAS DataBase Reference: (R)-3-AMINO-1-CBZ-PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-AMINO-1-CBZ-PYRROLIDINE(122536-73-6)
• EPA Substance Registry System: (R)-3-AMINO-1-CBZ-PYRROLIDINE(122536-73-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 122536-73-6(Hazardous Substances Data)

Usage

Uses

(R)-(?)-1-Cbz-3-aminopyrrolidine can be used:In one of the key synthetic steps for the preparations of AZ82, a KIFC1-specific inhibitor for cancer therapy.As a key intermediate in the synthesis of N6-substituted adenosine analogs as potent A1AR agonists.

InChI:InChI=1/C12H16N2O2.ClH/c13-11-6-7-14(8-11)12(15)16-9-10-4-2-1-3-5-10;/h1-5,11H,6-9,13H2;1H/t11-;/m1./s1

Upstream product

• 31139-36-3 dibenzyl dicarbonate 
• 116183-82-5 (R)-pyrrolidin-3-amine 
• 185057-50-5 (S)-3-Amino-1-pyrrolidinecarboxylic acid,phenylmethyl ester 
• 501-53-1 benzyl chloroformate 
• 122536-71-4 (R)-3-azido-1-pyrrolidinecarboxylic acid phenylmethyl ester 
• 122536-69-0 (S)-3-<(methylsulfonyl)oxy>-1-pyrrolidinecarboxylic acid phenylmethyl ester 
• 100858-32-0 (S)-3-hydroxy-1-pyrrolidinecarboxylic acid phenylmethyl ester 

Downstream Products

• 140412-80-2 (R)-3-((S)-2-tert-Butoxycarbonylamino-propionylamino)-pyrrolidine-1-carboxylic acid benzyl ester 
• 122536-75-8 Benzyl (3R)-3-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylate 

Relevant articles and documents

HETEROARYL COMPOUNDS AND THEIR USE AS MER INHIBITORS

Compounds of formula (I) [Formula should be inserted here] and a pharmaceutically acceptable salt thereof, wherein A, R1, R2, R3, R4, R5, R6, R7, R24, X, L, n and p are as defined in the specification, are useful for treating or preventing Mer tyrosine kinase receptor modulated disease or conditions. Also described are pharmaceutical compositions of compounds of formula (I), and methods for using such compounds and compositions.

Structure-activity relationships of adenosines with heterocyclic N6-substituents

Two series of N6-substituted adenosines with monocyclic and bicyclic N6 substituents containing a heteroatom were synthesized in good yields. These derivatives were assessed for their affinity ([3H]CPX), potency, and intrinsic activity (cAMP accumulation) at the A1 adenosine receptor in DDT1 MF-2 cells. In the monocyclic series, the N6-tetrahydrofuran-3-yl and thiolan-3-yl adenosines (1 and 26, respectively) were found to possess similar activities, whereas the corresponding selenium analogue 27 was found to be more potent. A series of nitrogen containing analogues showed varying properties, N6-((3R)-1-benzyloxycarbonylpyrrolidin-3-yl)adenosine (30) was the most potent at the A1AR; IC50 = 3.2 nM. In the bicyclic series, the effect of a 7-azabicyclo[2.2.1]heptan-2-yl substituent in the N6-position was explored. N6-(7-Azabicyclo[2.2.1]heptan-2-yl)adenosine (38) proved to be a reasonably potent A1 agonist (Ki = 51 nM, IC50 = 35 nM) while further substitution on the 7″-nitrogen with tert-butoxycarbonyl (31, IC50 = 2.5 nM) and 2-bromobenzyloxycarbonyl (34, IC50 = 9.0 nM) gave highly potent A1AR agonists.

Quinolone antibacterial agents. Synthesis and structure-activity relationships of a series of amino acid prodrugs of racemic and chiral 7-(3- amino-1-pyrrolidinyl)quinolones. Highly soluble quinolone prodrugs with in vivo pseudomonas activity

A series of amino acid prodrugs of racemic and chiral 7-(3-amino-1- pyrrolidinyl)-6-fluoro-1,8-naphthyridine-3-carboxylic acids, 1-cyclopropyl- 6,8-difluoro-3-quinolinecarboxylic acids, 1-cyclopropyl-6-fluoro-3- quinolinecarboxylic acids, and 5-amino-1-cyclopropyl-6,8-difluoro-3- quinolinecarboxylic acids have been prepared and evaluated for comparative antibacterial activity. Compounds were prepared by acylation of the 3-amino group of the pyrrolidine with common amino acids using standard peptide chemistry. This series has been compared with the parent compounds for antibacterial activity in vitro and in vivo as well as for comparative solubility. The amino acid analogues were less active in vitro, but had equal or increased efficacy in vivo. Indeed, it was proven that these compounds, which were stable to acid and base under the reaction conditions for their preparation, were rapidly cleaved in serum to give the parent quinolones. The amino acid derivatives showed a 3-70 times improved solubility when compared to the parent compounds. The most active compound of the series was [S- (R*,R*)]-7-[3-[(2-amino-1-oxopropyl)-amino]-1-pyrrolidinyl]-1-cyclopropyl- 6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (PD 131112).