820260-43-3

Upstream product

• 888073-56-1 (1S,2R,3R,5R,6S)-2-azido-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 
• 820260-67-1 (1S,1aS,1bS,4aR,5aR)-3,3-Dioxo-tetrahydro-2,4-dioxa-3λ⁶-thia-cyclopropa[a]pentalene-1,1b-dicarboxylic acid diethyl ester 
• 820260-64-8 (1S,2R,3R,5R,6S)-2-azido-3-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 
• 820260-66-0 (1S,5R,6S)-2,3-dihydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 
• 748780-77-0 3,4-dichlorobenzyl-2,2,2-trichloroacetoimidate 
• 1805-32-9 3,4-dichlorobenzyl alcohol 
• 892494-26-7 (1S,2R,3R,5R,6S)-2-azido-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester 
• 820260-55-7 (1S,2R,3R,5R,6S)-2-amino-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester 
• 820260-56-8 (1S,2R,3R,5R,6S)-2-amino-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 

Relevant academic research and scientific papers

Synthesis, in vitro pharmacology, and structure-activity relationships of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as mGluR2 antagonists

Chemical modification of the bicyclo[3.1.0]hexane ring C-3 position led to the discovery of 3-alkoxy-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 3-benzylthio-, and 3-benzylamino-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives, metabotropic glutamate receptor 2 (mGluR2) antagonists. In particular, 3-(3,4-dichlorobenzyloxy)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (15ae), (1R,2S,5R,6R)-2-amino-3-(3,4-dichlorobenzylthio)-6-fluorobicyclo[3.1.0]h exane-2,6-carboxylic acid (15at), and (1R,2S,5R,6R)-2-amino-3-(N-(3,4-dichlorobenzylamino))-6-fluorobicyclo[3. 1.0]hexane-2,6-carboxylic (15ba) showed high affinity for the mGluR2 receptor (15ae: Ki = 2.51 nM, 15at: Ki = 1.96 nM, and 15ba: Ki = 3.29 nM) and potent antagonist activity for mGluR2 (15ae; IC50 = 34.21 nM, 15at; IC50 = 13.34 nM, and 15ba; IC50 = 35.96 nM). No significant agonist activity for mGluR2 was observed with 15ae, 15at, or 15ba. This paper reports on the synthesis, in vitro pharmacological profile, and structure-activity relationships (SARs) of 3-substituted-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid.

Prodrugs of 3-(3,4-dichlorobenzyloxy)-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicar boxylic acid (MGS0039): A potent and orally active group II mGluR antagonist with antidepressant-like potential

3-(3,4-Dichlorobenzyloxy)-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicar boxylic acid 5 (MGS0039) is a highly selective and potent group II metabotropic glutamate receptor (mGluR) antagonist (antagonist activities for mGluR2; IC50 = 20.0 nM, mG