Convenient synthesis and isolation of conformationally rigid glutamic acid analogues

Synthetic Communications

Volumn 34, Issue 21, 2004, Pages 3939-3947

  Greenfield, A A ^a   Butera, J A ^a  

^a PFIZER INC   (United States)

Author keywords

Chiral HPLC; Hydantoin route; Restricted glutamate analogs

Indexed keywords

DICARBOXYLIC ACID DERIVATIVE; GLUTAMIC ACID DERIVATIVE; TRICYCLIC AMINODICARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; CHROMATOPHORE; DEPROTECTION REACTION; DIASTEREOISOMER; DRUG CONFORMATION; DRUG HYDROLYSIS; DRUG ISOLATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPOPHILICITY; OPTICAL ROTATION; REACTION ANALYSIS; REPRODUCIBILITY; SEPARATION TECHNIQUE; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 7644244589     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200034791     Document Type: Article

References (11)

1. Danysz, W.; Parsons, C.G.; Bresink, I.; Quack, G. Glutamate in CNS Disorders. Drug News and Perspectives 1995, 8 (5), 261-277.
2. Dunlop, J.; Zaleska, M.M.; Eliasof, S.; Moyer, J.A. Excitatory aminoacid transporters as emerging targets for central nervous system therapeutics. Emerging therapeutic targets 1999, 3 (4), 1-28.
3. Monn, J.A.; Valli, M.J.; Massey, S.M.; Hansen, M.M.; Kress, T.J.; Wepsiec, J.P.; Harkness, A.R.; Grutsch, J.L., Jr.; Wright, R.A.; Johnson, B.G.; Andis, S.L.; Kingston, A.; Tomlinson, R.; Lewis, R.; Griffey, K.R.; Tizzano, J.P.; Schoepp, D.D. Synthesis, pharmacological characterization, and molecular modeling of heterobicyclic amino acids related to (+)-2-aminobicyclo[3.1.0] hexane-2,6-dicarboxylic acid (LY354740): identification of two new potent, selective, and systemically active agonists for group II metabotropic glutamate receptors. J. Med. Chem 1999, 42, 1027-1040.
4. Tellier, F.; Acher, F.; Brabet, I.; Pin, J.-P.; Bockaert, J.; Azerad, R. Synthesis of conformationally-constrained stereospecific analogs of glutamic acid as antagonists of metabotropic receptors. Bioorg. Med. Chem. Lett 1995, 5 (22), 2627-2632.
5. Trigalo, F.; Buisson, D.; Azerad, R. Chemoenzymatic synthesis of conformationally rigid glutamic acid analogues. Tet. Lett 1988, 29 (47), 6109-6112.
6. Trigalo, F.; Acher, F.; Azerad, R. Synthesis and resolution of DHCGA, a new conformationally rigid 3,4-Dehydroglutamic acid analogue. Tetr 1990, 46 (15), 5203-5212.
7. Ndzie, E.; Cardinael, P.; Schoofs, A.R.; Coquerel, G. An efficient access to the enantiomers of alpha-methyl-4-carboxyphenylglycine via a hydantoin route using a practical variant of preferential crystallization AS3PC (auto seeded programmed polythermic preferential crystallization). Tetrahedron: Asymmetry 1997, 8 (17), 2913-2920.
8. Stack, Gary Paul; Dunlop, John; Greenfield, Alexander Alexei; Gross, Jonathan Laird. Preparation of bridged tricyclic analogs of 2- (carboxycyclopropyl)glycine as inhibitors of glutamate transport. PCT Int. Appl. 2003, WO 0302515 A1 20030109, Wyeth Research (USA).
9. Alder, K.; Hartmann, R.; Roth, W. Synthesen in der Bicyclo-[1.2.2]- heptan-Reihe. Darstellung von Nortricyclen-carbonsauren. Chem. Ber GE 1960, 93, 2271-2281.
10. It should be particularly noted that multipoint protection dramatically simplified chromatographic separations in a sense of both resolution and in capacities. Chiral separations could be performed successfully on a wide variety of commercially available chiral columns under a variety conditions.
11. Configurations have been assigned randomly.