(±)-(Z)-2-(Aminomethyl)-l-phenylcyclopropanecarboxamide Derivatives as a New Prototype of NMDA Receptor Antagonists

Journal of Medicinal Chemistry

Volumn 38, Issue 15, 1995, Pages 2964-2968

  Shuto, Satoshi ^a   Hase, Yukako ^a   Ono, Shizuka ^a   Shibuya, Nobuko ^a   Matsuda, Akira ^a   Takada, Hironao ^b   Mochizuki, Daisuke ^b   Tsujita, Ryuichi ^b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b ASAHI CHEMICAL INDUSTRY CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIDEPRESSANT AGENT; CYCLOPROPANE DERIVATIVE; DIZOCILPINE MALEATE; MILNACIPRAN; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; RECEPTORS, N METHYL D ASPARTATE; TRITIUM; 2 (2 AMINOETHYL) 1 PHENYLCYCLOPROPANE N,N DIETHYLCARBOXAMIDE; 2 [(N METHYLAMINO)METHYL] 1 PHENYLCYCLOPROPANE N,N DIETHYLCARBOXAMIDE; 2 [(N,N DIMETHYLAMINO)METHYL] 1 PHENYLCYCLOPROPANE N,N DIETHYLCARBOXAMIDE; 4 PHOSPHONOMETHYLPIPECOLIC ACID; BRAIN RECEPTOR; DIZOCILPINE; MAPROTILINE; N METHYL DEXTRO ASPARTIC ACID; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; KINETICS; MALE; METABOLISM; MOUSE; MOUSE STRAIN; RADIOASSAY; RAT; STRUCTURE ACTIVITY RELATION; SYNTHESIS; ANIMAL TISSUE; BRAIN MEMBRANE; DRUG ACTIVITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; RECEPTOR AFFINITY;

ANIMAL; ANTIDEPRESSIVE AGENTS; CYCLOPROPANES; DIZOCILPINE MALEATE; KINETICS; MALE; MICE; MICE, INBRED STRAINS; RADIOLIGAND ASSAY; RATS; RECEPTORS, N-METHYL-D-ASPARTATE; STRUCTURE-ACTIVITY RELATIONSHIP; TRITIUM;

EID: 0028991977     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00015a019     Document Type: Article

References (19)

1. Collingridge, G. L., Watkins, J. C., Eds. The NMDA Receptor, IRL Press at Oxford Univ. Press: Oxford UK, 1994.
2. Wong, E. H. F.; Kemp, J. A.; Priestly, T.; Knight, A. R.; Woodruff, G. N.; Iversen, L. L. The anticonvulsant MK-801 is a potent iV-methyl-D-aspartate antagonist. Proc. Natl. Acad. Sci. U. SA. 1986, 83, 7104-7108.
3. Gill, R.; Foster, A. C.; Woodruff, G. N. Systemic administration of MK-801 protects against ischaemia-induced hippocampal neurodegeneration in the gerbil. J. Neurosci. 1987, 7, 3343-3349.
4. Hutchison, A. J.; Williams, M.; Angst, C.; de Jesus, R.; Blanchard, L.; Jackson, R. H.; Wilusz, E. J.; Murphy, D. E.; Bernard, P. S.; Schneider, J.; Campbell, T.; Guida, W.; Sills, M. A. 4-(Phosphonoalkyl)- and 4-(phosphonoalkenyI)-2-piperidinecarboxylic acids: synthesis, activity at N-methyl-D-aspartic acid receptors, and anticonvulsant activity. J. Med. Chem. 1989, 32, 2171-2178.
5. Willetts, J.; Balster, R. L.; Leander, J. D. The behavioral pharmacology of NMDA receptor antagonists. Trends Pharmacol. Sci. 1990, 11, 423-428.
6. Tricklebank, M. D.; Singh, L.; Oles, R. J.; Preston, C.; Iversoen, S. D. The behavioral effects of MK-801: a comparison with antagonists acting non-competitively at the NMDA receptor. Eur. J. Pharmacol. 1989, 167, 127-135.
7. Olney, J. W.; Labruyere, J.; Price, M. T. Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs. Science 1989, 244, 1360-1362.
8. Meldrum, B. S.; Croucher, M. J.; Czuczwar, S. J.; Collins, J. F.; Curry, K.; Joseph, M.; Stone, T. W. A comparison of the anticonvulsant potency of (±)-2-amino-5-phosphonopentacoic acid and (±) 2-amino-7-phosphonoheptanoic acid. Neuroscience 1983, 9, 925-930.
9. Hogan, M. J.; Gjedde, A.; Hakem, A. M. In vivo distribution of CGS-19755 within brain in a model of focal cerebral ischemia. J. Neurochem. 1992, 58, 186-191.
10. Reynolds, I. J.; Miller, R. J. Tricyclic antidepressants block N-methyl-d-aspartate receptor; similarities to the action of zinc. Br. J. Pharmacol. 1988, 95, 95-102.
11. Semagor, E.; Kuhn, D.; Vyklicky, L., Jr.; Mayer, M. L. Open channel block of NMDA receptor responses evoked by tricyclic antidepressants. Neuron 1989, 2, 1221-1227.
12. 3H] GABA release. Eur. J. Pharmacol. Mol. Pharmacol. Sect. 1989, 172, 9-17.
13. Kitamura, Y.; Zhao, X.-H.; Takei, M.; Yonemitsu, O.; Nomura, Y. Effects of antidepressants of the glutaminergic system in mouse brain. Neurochem. Int. 1991, 19, 247-253.
14. Brukey, M. Midalcipran hydrochloride. Drugs Future 1986, 11, 21-23.
15. Moret, C.; Charveron, M.; Finberg, J. P. M.; Cozinier, J.; Briley, M. Biochemical profile of midalcipran (F- 2207). l-Phenyl-1-diethylaminocarbonyl-2-aminomethyl-cyclopropane (Z) hydrochloride, a potential fourth generation antidepressant drug. Neuropharmacology 1985, 24, 1211-1219.
16. Bonnaud, B.; Cousse, H.; Mouzin, G.; Briley, M.; Stenger, A.; Fauran, F.; Couzinier, J.-P. l-aryl-2-(aminomethyl) cyclopropane carboxylic acid derivatives. A new series of potential antidepressants. J. Med. Chem. 1987, 30, 318-325.
17. Mouzin, G.; Cousse, H.; Bonnaud, B. A convenient synthesis of bifunctional vicinal cyclopropanes. Synthesis 1978, 304-305.
18. Asano, T.; Ikegaki, I.; Satoh, S.; Mochizuki, D.; Hidaka, H.; Suzuki, Y.; Shibuya, M.; Sugita, K Blockade of intracellular actions of calcium may protect against ischaemic damage to the gerbil brain. Br. J. Pharmacol. 1991, 103, 1935-1938.
19. Rosen, T.; Seeger, T. F.; McLean, S.; Nagel, A. A.; Ives, J. L.; Guarino, K. J.; Bryce, D.; Furman, J. Benzo- and pyrido-1, 4-oxazepin-5-ones and -thiones: Synthesis and structure-activity relationships of a new series of Hi antihistamines. J. Med. Chem. 1990, 33, 3020-3199.