1427043-08-0

Basic information

• Product Name: (3R,5R,6S)-5,6-diphenyl-3-(2-(piperidin-1-yl)ethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)morpholin-2-one
• Synonyms: (3R,5R,6S)-5,6-diphenyl-3-(2-(piperidin-1-yl)ethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)morpholin-2-one
• CAS NO: 1427043-08-0
• Molecular Weight: 546.558
• Mol File: 1427043-08-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3R,5R,6S)-5,6-diphenyl-3-(2-(piperidin-1-yl)ethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)morpholin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5R,6S)-5,6-diphenyl-3-(2-(piperidin-1-yl)ethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)morpholin-2-one(1427043-08-0)
• EPA Substance Registry System: (3R,5R,6S)-5,6-diphenyl-3-(2-(piperidin-1-yl)ethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)morpholin-2-one(1427043-08-0)

Safety Data

• Hazardous Substances Data: 1427043-08-0(Hazardous Substances Data)

Upstream product

• 1345672-86-7 (3R,5R,6S)-tert-butyl 3-allyl-2-oxo-5,6-diphenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)-morpholine-4-carboxylate 
• 1345672-85-6 (3R,5R,6S)-tert-butyl 2-oxo-5,6-diphenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)morpholine-4-carboxylate 
• 1236275-93-6 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-iodobutane 
• 124215-50-5 2-(4-bromobutyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1427043-05-7 (3R,5R,6S)-tert-butyl 2-oxo-3-(2-oxoethyl)-5,6-diphenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-butyl)morpholine-4-carboxylate 

Downstream Products

• 1427043-09-1 (3R,5R,6S)-4-methyl-5,6-diphenyl-3-(2-(piperidin-1-yl)ethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)morpholin-2-one 

Relevant articles and documents

Discovery of (R)-2-amino-6-borono-2-(2-(piperidin-1-yl)ethyl)hexanoic acid and congeners as highly potent inhibitors of human arginases i and II for treatment of myocardial reperfusion injury

Recent efforts to identify treatments for myocardial ischemia reperfusion injury have resulted in the discovery of a novel series of highly potent α,α-disubstituted amino acid-based arginase inhibitors. The lead candidate, (R)-2-amino-6-borono-2-(2-(piperidin-1-yl)ethyl)hexanoic acid, compound 9, inhibits human arginases I and II with IC50s of 223 and 509 nM, respectively, and is active in a recombinant cellular assay overexpressing human arginase I (CHO cells). It is 28% orally bioavailable and significantly reduces the infarct size in a rat model of myocardial ischemia/reperfusion injury. Herein, we report the design, synthesis, and structure-activity relationships (SAR) for this novel series of inhibitors along with pharmacokinetic and in vivo efficacy data for compound 9 and X-ray crystallography data for selected lead compounds cocrystallized with arginases I and II.