1450621-79-0

Basic information

• Product Name: (3S)-1-benzyl-3-(2-propyn-1-yl)-piperazine
• Synonyms: (3S)-1-benzyl-3-(2-propyn-1-yl)-piperazine
• CAS NO: 1450621-79-0
• Molecular Weight: 214.31
• Mol File: 1450621-79-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (3S)-1-benzyl-3-(2-propyn-1-yl)-piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-1-benzyl-3-(2-propyn-1-yl)-piperazine(1450621-79-0)
• EPA Substance Registry System: (3S)-1-benzyl-3-(2-propyn-1-yl)-piperazine(1450621-79-0)

Safety Data

• Hazardous Substances Data: 1450621-79-0(Hazardous Substances Data)

Upstream product

• 1450621-78-9 (3S)-1-benzyl-3-(2-propyn-1-yl)-2,5-piperazinedione 
• 6436-90-4 ethyl 2-(benzylamino)acetate 
• 61172-66-5 (S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid 
• 1450621-77-8 ethyl 2-[benzyl-[(2S)-2-(tert-butoxycarbonylamino)pent-4-ynoyl]amino]acetate 

Downstream Products

• 1450620-96-8 2-(4-((2S)-4-((6-chloro-3-pyridazinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol 
• 1450620-95-7 2-(4-((2S)-4-((6-amino-3-pyridazinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol 
• 1450621-10-9 2-(4-((2S)-4-((6-amino-5-bromo-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol 
• 1450621-11-0 3-bromo-5-(((3S)-3-(1-propyn-1-yl)-4-(4-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-1-piperazinyl)sulfonyl)-2-pyridinol 
• 1450621-14-3 2-amino-5-(((3S)-3-(1-propyn-1-yl)-4-(4-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-1-piperazinyl)sulfonyl)-3-pyridinecarbonitrile 
• 1450620-25-3 (3S)-1-benzyl-3-(1-propyn-1-yl)piperazine 
• 1450621-80-3 2-(4-((2S)-4-benzyl-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol 
• 1450621-76-7 2-(4-((2S)-4-((2-amino-5-pyrimidinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol 
• 1450621-83-6 2-(6-((2S)-4-benzyl-2-(1-propyn-1-yl)-1-piperazinyl)-5-chloro-3-pyridinyl)-1,1,1,3,3,3-hexafluoro-2-propanol 
• 1450620-19-5 1,1,1,3,3,3-hexafluoro-2-(4-((2S)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-2-propanol 
• 1450621-12-1 C₂₁H₁₇BrClF₆N₃O₃S 
• 1572928-09-6 4-((2S)-4-benzyl-2-(1-propyn-1-yl)-1-piperazinyl)-N-cyclopropylbenzenesulfonamide 
• 1572928-10-9 N-cyclopropyl-4-((2S)-2-(1-propyn-1-yl)-1-piperazinyl)benzenesulfonamide 
• 1572928-11-0 tert-butyl (5-(((3S)-4-(4-(cyclopropylsulfamoyl)phenyl)-3-(1-propyn-1-yl)-1-piperazinyl)sulfonyl)-2-pyridinyl)carbamate 

Relevant articles and documents

Small molecule disruptors of the glucokinase-glucokinase regulatory protein interaction: 3. Structure-activity relationships within the aryl carbinol region of the N-arylsulfonamido-N′-arylpiperazine series

We have recently reported a novel approach to increase cytosolic glucokinase (GK) levels through the binding of a small molecule to its endogenous inhibitor, glucokinase regulatory protein (GKRP) these initial investigations culminated in the identification of 2-(4-((2S)-4-((6-amino-3- pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3, 3-hexafluoro-2-propanol (1, AMG-3969), a compound that effectively enhanced GK translocation and reduced blood glucose levels in diabetic animals. Herein we report the results of our expanded SAR investigations that focused on modifications to the aryl carbinol group of this series. Guided by the X-ray cocrystal structure of compound 1 bound to hGKRP, we identified several potent GK-GKRP disruptors bearing a diverse set of functionalities in the aryl carbinol region. Among them, sulfoximine and pyridinyl derivatives 24 and 29 possessed excellent potency as well as favorable PK properties. When dosed orally in db/db mice, both compounds significantly lowered fed blood glucose levels (up to 58%).

Nonracemic synthesis of GK-GKRP disruptor AMG-3969

A nonracemic synthesis of the glucokinase-glucokinase regulatory protein disruptor AMG-3969 (5) is reported. Key features of the synthetic approach are an asymmetric synthesis of the 2-alkynyl piperazine core via a base-promoted isomerization and a revised approach to the synthesis of the aminopyridinesulfonamide with an improved safety profile.