1564266-00-7

Basic information

• Product Name: 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3R,5S)-
• Synonyms: 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3R,5S)-;Saxagliptin (S,R,S,S)-Isomer;(1S,3R,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
• CAS NO: 1564266-00-7
• Molecular Formula: C₁₈H₂₅N₃O₂
• Molecular Weight: 315.41
• EINECS: -0
• Mol File: 1564266-00-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 548.7±35.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• PKA: 15.12±0.40(Predicted)
• CAS DataBase Reference: 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3R,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3R,5S)-(1564266-00-7)
• EPA Substance Registry System: 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3R,5S)-(1564266-00-7)

Safety Data

• Hazardous Substances Data: 1564266-00-7(Hazardous Substances Data)

Usage

Uses

(2’S,2R,trans)-Saxagliptin is an impurity of Saxagliptin (S143500); a potent and selective reversible inhibitor of dipeptidyl peptidase-4 (DPP-IV) developed for the treatment of type 2 diabetes.

Upstream product

• 68766-96-1 ethyl (R)-2-pyrrolidone-5-carboxylate 
• 144978-12-1 1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate 
• 361442-00-4 (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 361441-97-6 (alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 871727-40-1 2-tert-butyl 3-ethyl (1S,3R,5S)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate 
• 1091626-35-5 1-tert-butyl 2-ethyl (2R)-2,3-dihydro-1H-pyrrole-1,2-dicarboxylate 
• 932040-48-7 1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate 
• 102502-64-7 (S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride 
• 1564267-10-2 (S)-N-Boc-3-hydroxyadamantylglycine-D-trans-4,5-methanoprolinenitrile 

Relevant articles and documents

Synthesis and biological evaluation of all eight stereoisomers of DPP-IV inhibitor saxagliptin

All eight stereoisomers of saxagliptin have been synthesized and evaluated for their inhibitory activity against DPP-IV. It was unambiguously confirmed that the configuration of saxagliptin was critical to potent inhibition of DPP-IV. Docking study was performed to elucidate the configuration-activity relationship of saxagliptin stereoisomers. Tyr662 and Tyr470 have been suggested as the key residues of DPP-IV interacting with the inhibitors. This work provides valuable information for further inhibitor design against DPP-IV.