577773-32-1Relevant academic research and scientific papers
The synthesis of isotopically labeled (+)-2-amino-bicyclo[3.1.0]hexane-2,6- carboxylic acid and its 2-oxa-and 2-thia-analogs
Wheeler, William J.,O'Bannon, Douglas D.,Kennedy, Joseph H.,Monn, James A.,Tharp-Taylor, Roger W.,Valli, Matthew J.,Kuo, Fengjiun
, p. 605 - 620 (2005)
As part of a program aimed at the design of conformationally constrained analogs of glutamic acid, (+)-2-aminobicyclo[3.1.0]hexane-2,6-carboxylic acid (1), identified as a highly potent, selective, group II metabotropic glutamate receptor agonist has been synthesized and studied clinically. Heterocyclic analogs of 1 were subsequently synthesized in which the C-2 methylene has been replaced by an oxygen atom (2) or a sulfur atom (3). C-14 labeled isotopomers of 1, 2 and 3 have been synthesized to facilitate pre-clinical ADME studies. A tritium labeled isotopomer of 1 was also synthesized for use in in vitro experiments. A stable labeled isotopomer of rac-1 was prepared for use as an internal standard for bioanalytical assays. The key step in each of these syntheses was the reaction of chiral ketone 4, 5 or 6 with K14CN/ (NH4)2CO3 using the Bucherer-Berg protocol. In the preparation of the stable labeled isotopomer, rac-4-[13C 2] was prepared in two steps from ethyl bromoacetate-[UL- 13C2]; subsequent reaction of rac-4-[13C 2] with K13CN/15NH4Cl/Na 2CO3, followed by hydrolysis of the hydantoin yielded rac-1-[13C3, 15N]. Copyright
PRODRUGS OF EXCITATORY AMINO ACIDS
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Page 92, (2008/06/13)
This invention relates to synthetic excitatory amino acid prodrugs and processes for their preparation. The invention further relates to methods of using, and pharmaceutical compositions comprising, the compounds for the treatment of neurological disorder
