20448-79-7

Usage

Uses

Used in Cancer Therapy:
2-Amino-2-norbornanecarboxylic acid is used as a therapeutic target for the suppressive effect of I-type amino acid transporter 1 inhibition on human esophageal squamous cell carcinoma. It helps in inhibiting the growth and progression of cancer cells.
Used in Drug Development:
2-Amino-2-norbornanecarboxylic acid is used in the design and preparation of KMH-233, a selective and slowly reversible inhibitor of L-type amino acid transporter 1 (LAT1). 2-AMINO-2-NORBORNANECARBOXYLIC ACID potentiates the antiproliferative drug efficacy in cancer cells, enhancing the effectiveness of cancer treatments.

Biochem/physiol Actions

2-Amino-2-norbornanecarboxylic acid (BCH) is a Na(+)-independent system L specific substrate used with other system specific substrates such as the system A specific substrate α-(methylamino) isobutyric acid and system N specific substrate L-glutamic acid gamma-monohydroxamate to help identify, differentiate and characterize amino acid transport systems in cells.

InChI:InChI=1/C8H13NO2/c9-8(7(10)11)4-5-1-2-6(8)3-5/h5-6H,1-4,9H2,(H,10,11)

Upstream product

• 72431-82-4 methyl 2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate 
• 76637-59-7 (1S,4S)-2-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 72431-82-4 methyl 2-endo-acetamidobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate 
• 6203-08-3 methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 22264-49-9 spiro[bicyclo[2.2.1]heptane-2',5'-imidazolidine[2,4]dione] 
• 497-38-1 Norbornan-2-on 

Downstream Products

• 188751-57-7 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)bicyclo[2.2.1]heptane-2-carboxylic acid 
• 1398796-17-2 (S)-(9H-fluoren-9-yl)methyl 2-(1-cyano-2-(4'-((4-methylpiperazin-1-yl)methyl)biphenyl-4-yl)ethylcarbamoyl)bicyclo[2.2.1]heptan-2-ylcarbamate 
• 1398796-15-0 (S)-2-amino-N-(1-cyano-2-(4'-((4-methylpiperazin-1-yl)methyl)biphenyl-4-yl)ethyl)bicyclo[2.2.1]heptane-2-carboxamide 

Relevant academic research and scientific papers

A SYNTHESIS OF 2-AMINONORBORNENE-2-CARBOXYLIC ACID DERIVATIVES BY DIELS-ALDER REACTION USING α,β-DEHYDROALANINATES AS A DIENOPHILE

The Diels-Alder reaction of N-acyl-α,β-dehydroalanine esters with cyclopentadiene afforded a mixture of the stereoisomers of acylaminonorbornene-2-carboxylic acid esters in good yields.

New and facile synthesis of aminobicyclo[22.1]heptane-2-carboxylic acids

Abstract A facile approach for the stereoselective synthesis of a- and b-2-aminobicyclo[2.2.1]heptane-2-carboxylic acid is described. Substrate-controlled α-carboxylation of norbonene monoester delivered the asymmetric diester intermediate with high diastereoselectivity (up to 35:1). Sequential chemoselective ester cleavage, Curtius rearrangement, and hydrolysis gave the a- and b-isomers of 2-aminobicyclo[2.2.1]heptane-2-carboxylic acid, respectively.

PEPTIDYL NITRILCOMPOUNDS AS PEPTIDASE INHIBITORS

The invention relates to compounds of Formula (II) and their use in theraphy as peptidase inhibitors.

N-Fmoc-dehydroalanine: A versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids

The synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed. (C) 2000 Elsevier Science Ltd.