Enantiomerically pure tetrahydroquinoline derivatives as in vivo potent antagonists of the glycine binding site associated to the NMDA receptor

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 21, 2003, Pages 3863-3866

  Di Fabio, Romano ^a   Tranquillini, Elvira ^a   Bertani, Barbara ^a   Alvaro, Giuseppe ^a   Micheli, Fabrizio ^a   Sabbatini, Fabio ^a   Pizzi, Maria Domenica ^a   Pentassuglia, Giorgio ^a   Pasquarello, Alessandra ^a   Messeri, Tommaso ^a   Donati, Daniele ^a   Ratti, Emiliangelo ^a   Arban, Roberto ^a   Forno, Giovanna Dal ^a   Reggiani, Angelo ^b   Barnaby, Robert J ^a  

^a GSK   (Italy)

^b Biology Research   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG VEHICLE; GLYCINE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; NEUROPROTECTIVE AGENT; QUINOLINE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; BRAIN INJURY; BRAIN ISCHEMIA; CONTROLLED STUDY; CONVULSION; DRUG BINDING SITE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ENANTIOMER; MIDDLE CEREBRAL ARTERY OCCLUSION; NEUROPROTECTION; NONHUMAN; RAT;

EID: 12444339363     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.06.001     Document Type: Article

References (23)

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21. Compounds 3a-p: C, H and N analyses were within 0.4% of the theoretical values; mp were over 250°C.
22. D=-16° (c 0.25, DMSO).
23. After the completion of this study, the enantiomer 3c-(+) was re-synthesized (R. Di Fabio and G. Alvaro, unpublished results) following the same kind of asymmetric synthesis recently published for the preparation of some analogue THQ derivatives: Di Fabio, R.; Alvaro, G.; Bertani, B.; Donati, D.; Giacobbe, S.; Marchioro, C.; Palma, C.; Lynn, S. M. JOC, 2002, 67, 7319. By this approach, it was clearly proven that the absolute configuration of the C-2 stereogenic center of the enantiomer 3c-(+) was of type R.