β-analogs of PLG (L-prolyl-L-leucyl-glycinamide):: Ex-chiral pool syntheses and dopamine D2 receptor modulating effects

被引：24

作者：

Thomas, C

Ohnmacht, U

Niger, M

Gmeiner, P

机构：

[1] Univ Erlangen Nurnberg, Inst Pharm & Lebensmittelchem, D-91052 Erlangen, Germany

[2] Univ Bonn, Inst Anorgan Chem, D-53121 Bonn, Germany

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1998年 / 8卷 / 20期

关键词：

D O I：

10.1016/S0960-894X(98)00507-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Starting from (S)- and (R)-aspartic acid enantiomerically pure P-proline derivatives were synthesized. These chiral building blocks were transformed into P-analogs of the dopamine receptor modulating peptide PLG. According to dopamine receptor binding studies, significant enhancement of [H-3]pramipexole binding was observed for the isomeres 1a,b and 2a-c. The derivative Ib revealed an activity comparable to PLG. (C) 1998 Elsevier Science Ltd. Air rights reserved.

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页码：2885 / 2890

页数：6

相关论文

共 15 条

[1] NEUROLEPTIC DRUG-INDUCED DOPAMINE RECEPTOR SUPER-SENSITIVITY - ANTAGONISM BY L-PROLYL-L-LEUCYL-GLYCINAMIDE [J].

CHIU, S ;

PAULOSE, CS ;

MISHRA, RK .

SCIENCE, 1981, 214 (4526) :1261-1262

[2]

ELSWORTH JD, 1997, DOPAMINE RECEPTORS, P223, DOI [10.1007/978-1-4757-2635-0_8, DOI 10.1007/978-1-4757-2635-0_8]

[3] AN EFFICIENT AND PRACTICAL TOTAL SYNTHESIS OF (+)-VINCAMINE FROM L-ASPARTIC ACID [J].

GMEINER, P ;

FELDMAN, PL ;

CHUMOYER, MY ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3068-3074

[4] DOPAMINE AUTORECEPTOR AGONISTS - COMPUTATIONAL STUDIES, SYNTHESIS AND BIOLOGICAL INVESTIGATIONS [J].

GMEINER, P ;

SOMMER, J ;

MIERAU, J ;

HOFNER, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (08) :1477-1483

[5] ENANTIOMERICALLY PURE AMINO-ALCOHOLS AND DIAMINO ALCOHOLS FROM L-ASPARTIC ACID - APPLICATION TO THE SYNTHESIS OF EPISLAFRAMINE AND DIEPISLAFRAMINE [J].

GMEINER, P ;

JUNGE, D ;

KARTNER, A .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) :6766-6776

[6] 2-DIBENZYLAMINOBUTANE-1,4-DIOL - A VERSATILE INTERMEDIATE FOR A CHIROSPECIFIC BETA-AMINO ACID SYNTHESIS [J].

GMEINER, P ;

ORECHER, F ;

THOMAS, C ;

WEBER, K .

TETRAHEDRON LETTERS, 1995, 36 (03) :381-382

[7]

MISHRA RK, 1983, METHOD FIND EXP CLIN, V5, P203

[8]

OHNMACHT U, 1998, IN PRESS PHARMAZIE

[9]

REED LL, 1973, J AM CHEM SOC, V95, P7523, DOI 10.1021/ja00803a062

[10] ALKYLATION OF AMINO-ACIDS WITHOUT LOSS OF OPTICAL-ACTIVITY - ALPHA-ALKYLATION AND BETA-ALKYLATION OF AN ASPARTIC-ACID DERIVATIVE [J].

SEEBACH, D ;

WASMUTH, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (11) :971-971