Key intermediates in the synthesis of enantiopure antagonists at NMDA receptors: a structural study
Articolo
Data di Pubblicazione:
2005
Citazione:
Key intermediates in the synthesis of enantiopure antagonists at NMDA receptors: a structural study / G. Bombieri, N. Marchini, F. Meneghetti, A. Pinto, G. Roda. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 16:18(2005 Sep 19), pp. 3030-3035. [10.1016/j.tetasy.2005.07.034]
Abstract:
The two diastereomeric amino acid derivatives 8 (3aS,5R,6aS)-5-tert-butoxycarbonylamino-4,5,6,6a-tetrahydro-3aH-cyclopen ta[d]isoxazole-3,5-dicarboxylic acid diethyl ester, its epimer 9 (3aS,5S,6aS), and carboxylic acid 10 obtained by hydrolysis of 9, which are intermediates in the synthesis of novel NMDA receptor antagonists 6 and 7 (Fig. 1), have been characterized by X-ray studies at 293 K for 8 and 10, and at 100 K for 9. The configuration of the carbon binding the 5-tert-butoxycarbonylamino moiety (BOC) determines the different molecular complexity: the chain structure for 8, dimeric for 9, and chain dimers for 10. The pharmacophoric parameters in compound 8 (from which the active 7 is derived) are comparable with those observed for NMDA receptor antagonism, while 9 and 10 do not present the structural features, which match these pharmacophoric characteristics. (C) 2005 Elsevier Ltd. All rights reserved.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
G. Bombieri, N. Marchini, F. Meneghetti, A. Pinto, G. Roda
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