197142-33-9

Basic information

• Product Name: tert-butyl (3S)-3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate
• Synonyms: tert-butyl (3S)-3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate;tert-butyl (1R,3S,5R)-3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate
• CAS NO: 197142-33-9
• Molecular Formula: C₁₁H₁₉NO₃
• Molecular Weight: 213.27346
• Mol File: 197142-33-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: tert-butyl (3S)-3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (3S)-3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate(197142-33-9)
• EPA Substance Registry System: tert-butyl (3S)-3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate(197142-33-9)

Safety Data

• Hazardous Substances Data: 197142-33-9(Hazardous Substances Data)

Usage

General Description

Tert-butyl (3S)-3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate is a synthetic chemical compound that has a unique molecular structure containing a bicyclic ring system and a tert-butyl group. The compound is classified as an ester due to the presence of a carboxylate group, and the hydroxymethyl group attached to the bicyclic ring adds to its reactivity. This chemical is commonly used in pharmaceutical research and drug development due to its potential medicinal properties. Its specific configuration and functional groups make it a valuable building block for the synthesis of new molecules with therapeutic potential. Further studies are needed to explore the full range of applications and potential benefits of tert-butyl (3S)-3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate in various fields.

Upstream product

• 98-79-3 L-Pyroglutamic acid 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 138629-30-8 (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 1312338-82-1 D-cis-4,5-methanoprolineamide methanesulfonic acid salt 
• 1208008-33-6 (3S)-tert-butyl 3-(tert-butyldiphenylsiloxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate 
• 132974-83-5 (5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one 
• 1208008-34-7 (3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane 
• 197142-34-0 (1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 138629-30-8 (S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate 
• 197142-32-8 3-(tert-butyldiphenylsilanyloxymethyl)-2-azabicyclo[3.1.0]-hexane-2-carboxylic acid tert-butyl ester 
• 23696-40-4 trimethylstannylmethyl iodide 
• 17342-08-4 (S)-Pyroglutaminol 

Downstream Products

• 2414674-71-6 3-(6-chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]-hexane hydrochloride 
• 1373165-39-9 C₂₇H₃₇BN₄O₅ 
• 1373165-38-8 C₂₁H₂₄ClIN₄O₃ 
• 1373165-37-7 C₂₁H₂₅IN₄O₃ 
• 1369595-36-7 C₃₅H₃₂ClFN₄O₄ 
• 197142-34-0 (1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 

Relevant articles and documents

Discovery and Development of 3-(6-Chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane Hydrochloride (SUVN-911): A Novel, Potent, Selective, and Orally Active Neuronal Nicotinic Acetylcholine α4β2 Receptor Antagonist for the Treatment of Depression

A series of chemical optimizations guided by in vitro affinity at the α4β2 receptor in combination with selectivity against the α3β4 receptor, pharmacokinetic evaluation, and in vivo efficacy in a forced swim test resulted in identification of 3-(6-chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane hydrochloride (9h, SUVN-911) as a clinical candidate. Compound 9h is a potent α4β2 receptor ligand with a Ki value of 1.5 nM. It showed >10 μM binding affinity toward the ganglionic α3β4 receptor apart from showing selectivity over 70 other targets. It is orally bioavailable and showed good brain penetration in rats. Marked antidepressant activity and dose-dependent receptor occupancy in rats support its potential therapeutic utility in the treatment of depression. It does not affect the locomotor activity at doses several folds higher than its efficacy dose. It is devoid of cardiovascular and gastrointestinal side effects. Successful long-term safety studies in animals and phase-1 evaluation in healthy humans for safety, tolerability, and pharmacokinetics paved the way for its further development.

Structural Properties and Stereochemically Distinct Folding Preferences of 4,5-cis and trans-Methano- L -Proline Oligomers: The Shortest Crystalline PPII-Type Helical Proline-Derived Tetramer

The synthesis, structural properties, and folding patterns of a series of L-proline methanologues represented by cis- and trans-4,5-methano-L-proline amides and their oligomers are reported as revealed by X-ray crystallography, circular dichroism measurements, and DFT calculations. We disclose the first example of a crystalline tetrameric proline congener to exhibit a polyproline II helical conformation. Experimental evidence of PPII-type helical arrangement (both in solution and in the solid state) of cis-4,5-methano-L-proline oligomers is supported by theoretical calculations reflecting the extent of n→π? stabilization of the trans-amide conformation.

HEPATITIS C INHIBITOR COMPOUNDS

Compounds of Formula (I) and (II) wherein R1, R2, R3, R6, A and A' are defined herein. The compounds are useful as inhibitors of the function of NS5A protein encoded by HCV for the treatment of hepatitis C viral infection.