176199-48-7 Usage
Description
Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)(9CI) is a complex organic compound with a unique bicyclic structure and multiple functional groups, including a carboxylic acid and an amino group. Its stereochemistry is defined by the (1S,2S,5R,6S) configuration, which may contribute to its specific biological activities and interactions.
Uses
1. Used in Pharmaceutical Industry:
Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)(9CI) is used as a metabotropic glutamate receptor (mGluR) agonist for the treatment of general anxiety disorders and smoking cessation. Its agonist activity at group II mGluRs, such as LY 354740, may help modulate neuronal excitability and neurotransmission, providing therapeutic benefits in these conditions.
2. Used in Chemical Synthesis:
Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)(9CI) can be used as a building block or intermediate in the synthesis of various complex organic molecules, including pharmaceuticals, agrochemicals, and specialty chemicals. Its unique bicyclic structure and functional groups may offer specific advantages in the development of novel compounds with desired properties.
3. Used in Research and Development:
Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)(9CI) may serve as a valuable research tool for studying the structure-activity relationships of mGluR agonists and other biologically active molecules. Its unique stereochemistry and functional groups can provide insights into the design and optimization of new compounds with improved pharmacological profiles.
4. Used in Material Science:
The compound's unique structure and functional groups may also find applications in the development of novel materials with specific properties, such as chiral catalysts, enantioselective sensors, or functional polymers. Further research and development in this area could lead to new applications and technologies based on the properties of Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)(9CI).
Biological Activity
Highly selective and potent agonist of group II mGlu receptors (EC 50 values are 5.1 and 24.3 nM at mGlu 2 and mGlu 3 receptors respectively and > 100000 nM at mGlu 4 , mGlu 7 , mGlu 1a and mGlu 5a receptors). Displays antianxiety and antiaddictive activity in vivo . Orally and systemically active.
Check Digit Verification of cas no
The CAS Registry Mumber 176199-48-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,6,1,9 and 9 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 176199-48:
(8*1)+(7*7)+(6*6)+(5*1)+(4*9)+(3*9)+(2*4)+(1*8)=177
177 % 10 = 7
So 176199-48-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO4/c9-8(7(12)13)2-1-3-4(5(3)8)6(10)11/h3-5H,1-2,9H2,(H,10,11)(H,12,13)/t3-,4-,5-,8-/m0/s1
176199-48-7Relevant articles and documents
Constrained cycloalkyl analogues of glutamic acid: Stereocontrolled synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740) and its 6-phosphonic acid analogue
Krysiak, Jerzy,Midura, Wanda H.,Wieczorek, Wanda,Sieron, Leslaw,Mikolajczyk, Marian
experimental part, p. 1486 - 1493 (2010/11/04)
A new stereocontrolled synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2.6- dicarboxylic acid (LY354740) 1, a potent and selective 2mGluR agonist, has been accomplished in four steps with an overall yield of 27% starting from the enantiopure (+)-(R)-2-(p-tolylsulfinyl)cyclopent-2-enone 3. The key steps include asymmetric cyclopropanation of 3 with (dimethylsulfuranylidene)acetate (EDSA) and removal of the chiral p-tolylsulfinyl auxiliary from the cycloadduct ent-4c upon treatment with iso-propylmagnesium chloride. The stereoselective hydantoin formation from the bicyclic ketone 6 formed (Bucherer-Bergs reaction) and subsequent hydrolysis completed the synthesis of 1. The same reaction sequence has been applied in the first synthesis of enantiopure (+)-2-amino-6-phosphonobicyclo[3.0.1]hexane-2-carboxylic acid 2, a structural 6-phosphono analogue of 1. The starting bicyclic ketophosphonates 9-11 have been obtained by asymmetric cyclopropanation of (-)-(S)-3 with phosphoryl sulfonium ylides, producing only two endo-isomers. The major endo-isomer (+)-11a containing the 6-diisopropoxyphosphoryl group has been converted in three steps into (+)-endo-2 in 46% overall yield.
Enantiospecific synthesis of (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane- 2,6-dicarboxylic acid by a modified Corey-Link reaction
Dominguez, Carmen,Ezquerra, Jesus,Baker, S. Richard,Borrelly, Stephane,Prieto, Lourdes,Espada, Modesta,Pedregal, Carmen
, p. 9305 - 9308 (2007/10/03)
(1S,2S,5R,6S)-2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740) was synthesised enantiospecifically from a sugar derived enantiomerically pure cyclopentenone. The α-amino acid stereogenic centre was formed by reacting the ketone with chloroform anion and then the alcohol so formed was reacted with sodium azide/DBU in methanol to give an azido ester. Critically, this modified Corey-Link reaction gives the opposite stereochemical outcome to the traditional Bucherer-Bergs and Strecker reactions. The azide was reduced and acylated, the 1,2 diol deoxygenated and the protecting groups removed to give LY354740 with an e.e.>98%.
