SYNTHESIS OF 6-PHOSPHONOALKYL TETRAHYDRO-4-PYRIMIDINE-CARBOXYLIC ACIDS AS NMDA RECEPTOR ANTAGONISTS

被引：5

作者：

BIGGE, CF

WU, JP

DRUMMOND, JR

机构：

[1] Parke-Davis Pharmaceutical Research Division, Warner-Lambert Company, Ann Arbor, MI 48105

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 52期

关键词：

6-PHOSPHONOALKYL TETRAHYDRO-4-PYRIMIDINECARBOXYLIC ACIDS; NMDA ANTAGONIST; MICHAEL REACTION;

D O I：

10.1016/0040-4039(91)80558-N

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compounds were prepared via a sequence which involved as the key steps a Michael reaction between nitroalkyl phosphonates and protected dehydroalanine and subsequent cyclization of the alpha, gamma-diamino esters.

引用

页码：7659 / 7662

页数：4

共 9 条

[1] MICHAEL ADDITIONS OF NITROALKANES TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS USING KF BASIC ALUMINA [J].

BERGBREITER, DE ;

LALONDE, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) :1601-1603

[2] EXPLORATION OF PHENYL-SPACED 2-AMINO-(5-9)-PHOSPHONOALKANOIC ACIDS AS COMPETITIVE N-METHYL-D-ASPARTIC ACID ANTAGONISTS [J].

BIGGE, CF ;

DRUMMOND, JT ;

JOHNSON, G ;

MALONE, T ;

PROBERT, AW ;

MARCOUX, FW ;

COUGHENOUR, LL ;

BRAHCE, LJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1580-1590

[3] ANTICONVULSANT ACTION OF EXCITATORY AMINO-ACID ANTAGONISTS [J].

CROUCHER, MJ ;

COLLINS, JF ;

MELDRUM, BS .

SCIENCE, 1982, 216 (4548) :899-901

[4] NEW AND VERSATILE APPROACHES TO THE SYNTHESIS OF CPP-RELATED COMPETITIVE NMDA ANTAGONISTS - PRELIMINARY STRUCTURE-ACTIVITY-RELATIONSHIPS AND PHARMACOLOGICAL EVALUATION [J].

HAYS, SJ ;

BIGGE, CF ;

NOVAK, PM ;

DRUMMOND, JT ;

BOBOVSKI, TP ;

RICE, MJ ;

JOHNSON, G ;

BRAHCE, LJ ;

COUGHENOUR, LL .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) :2916-2924

[5] 4-(PHOSPHONOALKYL)-2-PIPERIDINECARBOXYLIC AND 4-(PHOSPHONOALKENYL)-2-PIPERIDINECARBOXYLIC ACIDS - SYNTHESIS, ACTIVITY AT N-METHYL-D-ASPARTIC ACID RECEPTORS, AND ANTICONVULSANT ACTIVITY [J].

HUTCHISON, AJ ;

WILLIAMS, M ;

ANGST, C ;

DEJESUS, R ;

BLANCHARD, L ;

JACKSON, RH ;

WILUSZ, EJ ;

MURPHY, DE ;

BERNARD, PS ;

SCHNEIDER, J ;

CAMPBELL, T ;

GUIDA, W ;

SILLS, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (09) :2171-2178

[6]

LEHMANN J, 1988, J PHARMACOL EXP THER, V246, P65

[7] NITROETHYLENE - STABLE, CLEAN, AND REACTIVE AGENT FOR ORGANIC-SYNTHESIS [J].

RANGANATHAN, D ;

RAO, CB ;

RANGANATHAN, S ;

MEHROTRA, AK ;

IYENGAR, R .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (07) :1185-1189

[8] BLOCKADE OF N-METHYL-D-ASPARTATE RECEPTORS MAY PROTECT AGAINST ISCHEMIC DAMAGE IN THE BRAIN [J].

SIMON, RP ;

SWAN, JH ;

GRIFFITHS, T ;

MELDRUM, BS .

SCIENCE, 1984, 226 (4676) :850-852

[9] HYPOGLYCEMIA-INDUCED NEURONAL DAMAGE PREVENTED BY AN N-METHYL-D-ASPARTATE ANTAGONIST [J].

WIELOCH, T .

SCIENCE, 1985, 230 (4726) :681-683

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