1374334-12-9

Basic information

• Product Name: sin-tert-butyl 3-acetamido-4-allyl-3-(tert-butylcarbamoyl)pyrrolidine-1-carboxylate
• CAS NO: 1374334-12-9
• Molecular Weight: 367.489
• Mol File: 1374334-12-9.mol

Chemical Properties

• CAS DataBase Reference: sin-tert-butyl 3-acetamido-4-allyl-3-(tert-butylcarbamoyl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: sin-tert-butyl 3-acetamido-4-allyl-3-(tert-butylcarbamoyl)pyrrolidine-1-carboxylate(1374334-12-9)
• EPA Substance Registry System: sin-tert-butyl 3-acetamido-4-allyl-3-(tert-butylcarbamoyl)pyrrolidine-1-carboxylate(1374334-12-9)

Safety Data

• Hazardous Substances Data: 1374334-12-9(Hazardous Substances Data)

Upstream product

• 4530-20-5 BOC-glycine 
• 119072-55-8 tert-butylisonitrile 
• 120871-73-0 3-allyl-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 631-61-8 ammonium acetate 
• 1374334-11-8 3-allyl 1-tert-butyl 4-oxopyrrolidine-1,3-dicarboxylate 
• 194924-95-3 4-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl 3-methyl ester 
• 120871-72-9 (+/-)-tert-butyl trans-4-allyl-3-hydroxypyrrolidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 114214-49-2 1-tert-butoxycarbonyl-3,4-epoxypyrrolidine 

Relevant articles and documents

Discovery of N-Substituted 3-Amino-4-(3-boronopropyl)pyrrolidine-3-carboxylic Acids as Highly Potent Third-Generation Inhibitors of Human Arginase i and II

Recent efforts to identify new highly potent arginase inhibitors have resulted in the discovery of a novel family of (3R,4S)-3-amino-4-(3-boronopropyl)pyrrolidine-3-carboxylic acid analogues with up to a 1000-fold increase in potency relative to the current standards, 2-amino-6-boronohexanoic acid (ABH) and N-hydroxy-nor-l-arginine (nor-NOHA). The lead candidate, with an N-2-amino-3-phenylpropyl substituent (NED-3238), example 43, inhibits arginase I and II with IC50 values of 1.3 and 8.1 nM, respectively. Herein, we report the design, synthesis, and structure-activity relationships for this novel series of inhibitors, along with X-ray crystallographic data for selected examples bound to human arginase II.

METHOD OF PREPARING (3R,4S)-3-ACETAMIDO-4-ALLYL-N-(TERT-BUTYL)PYRROLIDINE-3-CARBOXAMIDE

A method is provided to conveniently separate racemic (3R,4S)-3-acetamido-4-allyl-N-(tert-butyl)pyrrolidine-3-carboxamide and (3S,4R)-3-acetamido-4-allyl-N-(tert-butyl)pyrrolidine-3-carboxamide using selective crystallization with chiral carboxylic acids.

BORONATES AS ARGINASE INHIBITORS

Compounds according to Formula I are potent inhibitors of Arginase I and II activity: (I) where R1, R2, R3, R4, D, W, X, Y, and Z are defined in the specification. The invention also provides pharmaceutical compositions of the compounds and methods of their use in treating or preventing a disease or a condition associated with arginase activity.