120871-73-0

Usage

Uses

Used in Pharmaceutical Industry:
tert-Butyl 3-allyl-4-oxopyrrolidine-1-carboxylate is used as a building block for the synthesis of various pharmaceuticals and biologically active molecules. Its unique structural properties and reactivity make it a valuable component in the development of new drugs and therapeutic agents.
Used in Chemical Industry:
In the chemical industry, tert-Butyl 3-allyl-4-oxopyrrolidine-1-carboxylate is utilized as an intermediate in the synthesis of various organic compounds. Its versatility and reactivity contribute to the production of a wide range of chemical products, including specialty chemicals and advanced materials.

Upstream product

• 73286-70-1 N-(tert-butoxycarbonyl)-3-pyrroline 
• 120871-72-9 (+/-)-tert-butyl trans-4-allyl-3-hydroxypyrrolidine-1-carboxylate 
• 897043-47-9 3-allyl-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester 
• 114214-49-2 1-tert-butoxycarbonyl-3,4-epoxypyrrolidine 
• 194924-95-3 4-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl 3-methyl ester 
• 1374334-11-8 3-allyl 1-tert-butyl 4-oxopyrrolidine-1,3-dicarboxylate 
• 4530-20-5 BOC-glycine 

Downstream Products

• 1374334-12-9 tert-butyl (3R,4S)-3-acetamido-4-allyl-3-(tert-butylcarbamoyl)pyrrolidine-1-carboxylate 
• 120871-72-9 trans-tert-butyl 3-allyl-4-hydroxypyrrolidine-1-carboxylate 
• 1374334-12-9 (syn-racemic) tert-butyl-3-acetamido-4-allyl-3-(tert-butylcarbamoyl)pyrrolidine-1-carboxylate 
• 1374334-12-9 sin-tert-butyl 3-acetamido-4-allyl-3-(tert-butylcarbamoyl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

PROCESSES FOR THE PREPARATION OF ARGINASE INHIBITORS AND THEIR SYNTHETIC INTERMEDIATES

Provided herein are processes and intermediates useful for the preparation of certain compounds, including a compound of formula 21 or formula 22 or a pharmaceutically acceptable salt of either.

Compound as well as preparation method and medical application thereof

The invention provides a compound as well as a preparation method and medical application thereof, the compound has a structure as shown in a general formula (I), and can also be a tautomer, a mesomer, a raceme, an enantiomer, a diastereoisomer, or a mixture form thereof, or a pharmaceutically acceptable salt thereof. According to the compound with the structure as shown in the general formula (I)provided by the invention, a specific main chain structure and a corresponding substituent group are selected, so that the obtained compound can be used as an arginase inhibitor, is relatively high in activity, and has a potential treatment prospect in various diseases.

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.

COMPOSITIONS AND METHODS FOR INHIBITING ARGINASE ACTIVITY

The invention relates to a novel class of compounds that exhibit activity inhibitory activity toward arginase, and pharmaceutical compositions comprising the compounds of the invention. Also provided herein are methods of treating cancer with the arginase inhibitors of the invention.

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.