134795-25-8

Basic information

• Product Name: (3S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid
• Synonyms: (3S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid;2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid;Rel-(1S,3R,4R)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid;Racemic-(1S,3R,4R)-2-(Tert-Butoxycarbonyl)-2-Azabicyclo[2.2.1]Heptane-3-Carboxylic Acid
• CAS NO: 134795-25-8
• Molecular Formula: C12H19NO4
• Molecular Weight: 241.28356
• Mol File: 134795-25-8.mol
• Article Data: 39

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (3S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid(134795-25-8)
• EPA Substance Registry System: (3S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid(134795-25-8)

Safety Data

• Hazardous Substances Data: 134795-25-8(Hazardous Substances Data)

Usage

General Description

The chemical "(3S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid" is a compound with a complex molecular structure, containing both a bicyclic ring system and a carboxylic acid functional group. The "3S" designation indicates the stereochemistry of the compound, specifically the configuration of the substituents around the third carbon atom in the bicyclic ring. The addition of the tert-butoxycarbonyl group to the compound provides protection for the amine functional group, while the presence of the carboxylic acid moiety suggests potential for involvement in biochemical processes. Overall, this compound represents a chemically and structurally intricate molecule with potential applications in synthetic organic chemistry and pharmaceutical research.

Upstream product

• 130194-96-6 (1S,3S,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid methyl ester 
• 88260-08-6 2-azabicyclo[2.2.1.]heptane-3-carboxylic acid,ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 171754-03-3 (1S,3R,4R)-2-aza-bicyclo-[2.2.1]-heptane-3-carboxylic acid 
• 26250-84-0 (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid 
• 81357-21-3 ethyl (+/-)-N-tert-butyloxycarbonyl-2-azanorborn-5-ene-3-exo-carboxylate 
• 188057-42-3 ethyl (1R,3S,4S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate 
• 134984-63-7 (1S,3S,4R)-2-((R)-1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester 
• 1181573-36-3 (1R,3S,4S)-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester 
• 220093-41-4 (1R,3S,4S)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid methyl ester 
• 171754-02-2 (1S,3S,4R)-2-azabicyclo<2.2.1>heptane-3-carboxylic acid 
• 764622-98-2 (1S,3S,4R)-2-Aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester 
• 192461-70-4 ethyl (1R,3S,4S)-2-<(R)-1-phenylethyl>-2-azabicyclo<2.2.1>heptane-3-exo-carboxylate 
• 542-92-7 cyclopenta-1,3-diene 

Downstream Products

• 1321849-48-2 C₅₀H₅₀N₈O₆ 
• 1256383-53-5 (1R,3S,4S)-3-[4-(4-bromo-phenyl)-1H-imidazol-2-yl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 1256387-76-4 (1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate 
• 1256387-75-3 (1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate 
• 1256387-78-6 methyl (S)-1-((S)-2-(5-(4'-(2-((1R,3S,4S)-2-((S)-2-(acetoxyamino)-3-methylbutanoyl)-2-azabicyclo[2.2.1]heptan-3-yl)-1H-benzo[d]imidazol-6-yl)biphenyl-4-yl)-1Himidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate 
• 1256388-51-8 methyl [(2S)-1-{(6S)-6-[5-(9,9-difluoro-7-{2-[(1R,3S,4S)-2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-azabicyclo[2.2.1]-hept-3-yl]-1H-benzimidazol-6-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl}-3-methyl-1-oxobutan-2-yl]carbamate 
• 1256383-53-5 (1R,3S,4S)-tert-butyl 3-(5-(4-bromophenyl)-1H-imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate 

Relevant articles and documents

Design, Synthesis and Biological Evaluation of Neogliptin, a Novel 2-Azabicyclo[2.2.1]heptane-Based Inhibitor of Dipeptidyl Peptidase-4 (DPP-4)

Compounds that contain (R)-3-amino-4-(2,4,5-trifluorophenyl)butanoic acid substituted with bicyclic amino moiety (2-aza-bicyclo[2.2.1]heptane) were designed using molecular modelling methods, synthesised, and found to be potent DPP-4 (dipeptidyl peptidase-4) inhibitors. Compound 12a (IC50 = 16.8 ± 2.2 nM), named neogliptin, is a more potent DPP-4 inhibitor than vildagliptin and sitagliptin. Neogliptin interacts with key DPP-4 residues in the active site and has pharmacophore parameters similar to vildagliptin and sitagliptin. It was found to have a low cardiotoxic effect compared to sitagliptin, and it is superior to vildagliptin in terms of ADME properties. Moreover, compound 12a is stable in aqueous solutions due to its low intramolecular cyclisation potential. These findings suggest that compound 12a has unique properties and can act as a template for further type 2 diabetes mellitus drug development.

ALKYNE COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is alkyne substituent (R32) are provided. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade. The inhibitors of Factor D described herein can reduce the excessive activation of complement.

AMIDE COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is an amide substituent (R32) are provided. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade. The inhibitors of Factor D described herein are capable of reducing the excessive activation of complement.