109523-16-2

Basic information

• Product Name: 2(S)-Aza-bicyclo[2.2.2]octane-2,3-dicarboxylic acid 2-tert-butyl ester
• Synonyms: 2(S)-Aza-bicyclo[2.2.2]octane-2,3-dicarboxylic acid 2-tert-butyl ester;(1S,3R,4S)-2-(Tert-Butoxycarbonyl)-2-Azabicyclo[2.2.2]Octane-3-Carboxylic Acid;Racemic-(1R,3S,4R)-2-(Tert-Butoxycarbonyl)-2-Azabicyclo[2.2.2]Octane-3-Carboxylicacid;(2S)-3-tert-butoxycarbonyl-3-azabicyclo[2,2,2]octane-2-carboxylic acid;Racemic-(1R,3S,4R)-2-(Tert-Butoxycarbonyl)-2-Azabicyclo[2.2.2]Octane-3-Carboxylicacid(WX120004);(3S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[2.2.2]octane-3-carboxylic acid
• CAS NO: 109523-16-2
• Molecular Formula: C₁₃H₂₁NO₄
• Molecular Weight: 255.31014
• Mol File: 109523-16-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(S)-Aza-bicyclo[2.2.2]octane-2,3-dicarboxylic acid 2-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2(S)-Aza-bicyclo[2.2.2]octane-2,3-dicarboxylic acid 2-tert-butyl ester(109523-16-2)
• EPA Substance Registry System: 2(S)-Aza-bicyclo[2.2.2]octane-2,3-dicarboxylic acid 2-tert-butyl ester(109523-16-2)

Safety Data

• Hazardous Substances Data: 109523-16-2(Hazardous Substances Data)

Usage

General Description

2(S)-Aza-bicyclo[2.2.2]octane-2,3-dicarboxylic acid 2-tert-butyl ester is a chemical compound with the molecular formula C14H23NO4. It is a derivative of aza-bicyclic compounds, which are known for their various pharmacological activities. This particular compound is commonly used in the pharmaceutical industry as a building block for the synthesis of a variety of biologically active compounds. Its tert-butyl ester functional group makes it a versatile intermediate in organic synthesis, allowing for the creation of more complex molecules. Additionally, this compound has potential applications in the fields of medicinal chemistry and drug discovery due to its unique structure and properties.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 109583-12-2 (3S)-2-azabicyclo<2.2.2>octane-3-carboxylic acid 

Downstream Products

• 387337-32-8 methyl 2-(S)-[(2-benzenesulfonyl-2-(S)-azabicyclo[2.2.2]octane-3-carbonyl)amino]-3-(4-dimethylcarbamoyloxyphenyl)propanoate 
• 896448-48-9 methyl 2-(S)-[(2-(S)-N-(t-butyloxycarbonyl)azabicyclo[2.2.2]octane-3-carbonyl)amino]-3-(4-dimethylcarbamoyloxyphenyl)propanoate 

Relevant articles and documents

SUBSTITUTED 2-AZA-BICYCLO[2.2.2]OCTANE-3-CARBOXYLIC ACID (BENZYL-CYANO-METHYL)-AMIDES INHIBITORS OF CATHEPSIN C

This invention relates to 2-Aza-bicyclo[2.2.2]octane-3-carboxylic acid (benzyl-cyano-methyl)-amides of formula 1 and their use as inhibitors of Cathepsin C, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of diseases connected with dipeptidyl peptidase I activity, e.g. respiratory diseases.

Selection of a 2-azabicyclo[2.2.2]octane-based α4β1 integrin antagonist as an inhaled anti-asthmatic agent

The α4β1 integrin, expressed on eosinophils and neutrophils, induces inflammation in the lung by facilitating cellular infiltration and activation. From a number of potent α4β1 antagonists that we evaluated for

New prolyl endopeptidase inhibitors: In vitro and in vivo activities of azabicyclo[2.2.2]octane, azabicyclo[2.2.1]heptane, and perhydroindole derivatives

A series of potent and selective prolylendopeptidase (PEP) inhibitors of the α-keto heterocyclic type has been obtained by replacing the classical central proline of 1-[1-(4-phenylbutanoyl)-L-prolyl]pyrrolidine (SUAM 1221, 3) by non-natural amino acids PHI, ABO, and ABH. These 4-phenylbutanoyl side- chain-containing inhibitors exhibited potent in vitro inhibitory potencies with IC50 around 30 nM (compounds 24 and 25). Modulation of the side chain by replacement of the terminal phenyl ring by the dicyclopropyl moiety afforded derivatives 30 and 32 with improved potencies (IC50 between 10 and 20 nM). Furthermore, replacing the linear 4-phenylbutanoyl side chain by the (2-phenylcyclopropyl)carbonyl entity provided potent inhibitors with IC50 culminating at 0.9 nM on a rat cortex enzymatic preparation (compound 70). The configuration of the cyclopropyl ring had to be R,R in order to obtain not only a strong PEP inhibition in vitro but also a good activity in vivo, exemplified by inhibitor 68, which gave ID50 ip and po of 0.3 and 1 mg/kg, respectively. Finally, demonstration of the cognition-enhancing properties of compound 54 was given in the passive avoidance test using scopolamine- induced amnesia in the rat, where it dose dependently inhibited the scopolamine-induced decrease in avoidance response.