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.
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]
Key intermediates in the synthesis of enantiopure antagonists at NMDA receptors: a structural study
G. Bombieri
Primo
;F. Meneghetti;A. PintoPenultimo
;G. RodaUltimo
2005
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.File | Dimensione | Formato | |
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