234085-20-2

Basic information

• Product Name: Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-3-fluoro-, (1S,2S,3S,5R,6S)- (9CI)
• Synonyms: Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-3-fluoro-, (1S,2S,3S,5R,6S)- (9CI)
• CAS NO: 234085-20-2
• Molecular Formula: C8H10FNO4
• Molecular Weight: 203.1677032
• Product Categories: AMINOACID
• Mol File: 234085-20-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-3-fluoro-, (1S,2S,3S,5R,6S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-3-fluoro-, (1S,2S,3S,5R,6S)- (9CI)(234085-20-2)
• EPA Substance Registry System: Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-3-fluoro-, (1S,2S,3S,5R,6S)- (9CI)(234085-20-2)

Safety Data

• Hazardous Substances Data: 234085-20-2(Hazardous Substances Data)

Upstream product

• 234085-35-9 ethyl (1R,2R,3R,5S,6R)-2-spiro-5'-hydantoin-3-fluorobicyclo[3.1.0]hexane-6-carboxylic acid 
• 134176-18-4 (+/-)-(1S,5R,6S)-ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate 
• 234085-33-7 ethyl (1S,2S,3S,5R,6S)-2-spiro-5'-hydantoin-3-fluorobicyclo[3.1.0]hexane-6-carboxylic acid 
• 268226-83-1 (1S,5R,6S)-2-[(trimethylsilyl)oxy]bicyclo[3.1.0]hex-2-ene-6-carboxylic acid ethyl ester 
• 268226-75-1 ethyl (1S, 3R, 4R, 5R, 6S)-3,4-epoxy-2-oxobicyclo[3.1.0]hexane-6-carboxylate 
• 278176-02-6 ethyl (1S, 3S, 5R, 6S)-3-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate 
• 278175-96-5 ethyl (1S,3R,4R,5R,6S)-3-fluoro-2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylate 
• 188885-85-0 (1S,5R,6S)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 
• 188885-82-7 ethyl (1SR,5RS,6SR)-2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylate 
• 278176-04-8 ethyl (1S,2S,3S,5R,6S)-2-spiro-5'-hydantoin-3-fluorobicyclo[3.1.0]hexane-6-carboxylate 

Relevant articles and documents

PRODRUG OF FLUORINE-CONTAINING AMINO ACID

Provided are a fluorine-containing amino acid prodrug represented by general formula (I) that makes a fluorine-containing amino acid which is a group 2 metabotropic glutamate receptor agonist into a prodrug, or a pharmaceutically acceptable salt thereof. More specifically, provided is a prodrug that increases the in vivo exposure and enhances the oral absorbability and other mucosal absorbability of a parent compound that acts on group 2 metabotropic glutamate receptors as an agent for the treatment or prevention of diseases in which group 2 metabotropic glutamate receptors are said to be involved, such as: schizophrenia, anxiety disorder and its related diseases, depression, bipolar disorder, epilepsy, developmental disorders, sleep disorders, and other neuropsychiatric diseases; and drug dependence, cognitive disorders, Alzheimer's disease, Huntington's chorea, Parkinson's disease, movement disorders associated with muscular rigidity, cerebral ischemia, cerebral insufficiency, spinal cord disorders, cephalopathy, and other neurological diseases.

Scalable synthesis of (+)-2-amino-3-fluorobicyclo[3.1.0]hexane-2,6- dicarboxylic acid as a potent and selective group II metabotropic glutamate receptor agonist

We successfully synthesized the potent and selective group II mGluR agonist (+)-1 (MGS0008) via a process incorporating the key step of efficient fluorination of epoxide (±)-5c. This method would be adaptable to large-scale synthesis to produce (+)-1 in m

Intermediates and process for producing fluorine-containing amino acid compound by using the same

The present inventions relate to a (1S,5R,6S)- or (1SR, 5RS, 6SR)-3-fluoro-2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylic acid derivative represented by Formula (1): [in the formula, R represents OR1or NR1R2, wherein R1and R2are identical or different, and each represents a hydrogen atom, a C1-C6alkyl group, a C3-C6cycloalkyl group, a (C3-C6cycloalkyl) (C1-C6alkyl) group, an aryl group, an aryl (C1-C6alkyl) group, a (C1-C6alkoxy) (C1-C6alkyl) group, a C1-C6hydroxyalkyl group, a (C1-C6alkylthio) (C1-C6alkyl) group, or a C1-C6mercaptoalkyl group], and a process for producing the same, and a process for efficiently producing a fluorine-containing amino acid compound acting on group 2 metabotropic glutamate receptors, which has treatment effects or prevention effects on psychiatric diseases or neurological diseases, characterized by hydrogenating the derivative, and subsequently, subjecting it to hydantoination or aminocyanidation, followed by hydrolysis.

Fluorine-containing amino acid derivatives

Fluorine-containing amino acid derivatives represented general formula (I), pharmaceutically acceptable salts thereof or hydrates of the same, wherein X1represents hydrogen or fluorine; and R1and R2are the same or different and each represents hydrogen or lower C1-10alkyl. These compounds are useful as drugs, in particular, group 2 metabotropic glutamate receptor agonists for treating and preventing psychiatric disorders such as schizophrenia, anxiety and associated diseases, depression, bipolar disturbance and epilepsy, and neurological diseases such as drug addiction, cognition disorder, Alzheimer's disease, Huntington's chorea, Parkinson's disease, motility disturbance associating muscular stiffness, cerebral ischemia, cerebral insufficiency, spinal cord lesion and head disturbance.

Synthesis, SARs, and pharmacological characterization of 2-Amino-3 or 6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as potent, selective, and orally active group II metabotropic glutamate receptor agonists

(+)-2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (4, LY354740), a highly selective and orally active group II metabotropic glutamate receptor (mGluR) agonist, has increased interest in the study of group II mGluRs. Our interest focused on a conformat