Synthesis and dopamine receptor modulating activity of unsubstituted and substituted triproline analogues of L-prolyl-L-leucyl-glycinamide (PLG)

被引：19

作者：

Baures, PW

Pradhan, A

Ojala, WH

Gleason, WB

Mishra, RK

Johnson, RL ^{[1
]}

机构：

[1] Univ Minnesota, Dept Med Chem, Minneapolis, MN 55455 USA

[2] Univ Minnesota, Ctr Biomed Engn, Minneapolis, MN 55455 USA

[3] Univ Minnesota, Dept Lab Med & Pathol, Minneapolis, MN 55455 USA

[4] McMaster Univ, Dept Psychiat & Biobehav Sci, Hamilton, ON L8N 3Z5, Canada

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 16期

关键词：

D O I：

10.1016/S0960-894X(99)00386-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Triprolines Pro-Pro-Pro-NH2 (4), Pro-Pro-D-Pro-NH2 (5), Pro-Pro(trans-3-Me)-D-Pro-NH2 (6), and Pro-Pro(cis-3-Me)-D-Pro-NH2 (7) were made as conformationally constrained analogues of Pro-Leu-Gly-NH2. Triprolines 4-6 produced significant increases in the high- and low-affinity state ratio (R-H/R-L) of the dopamine receptor, but only 4 was found to increase apomorphine induced rotations in 6-hydroxydopamine-lesioned rats. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2349 / 2352

页数：4

相关论文

共 23 条

[1] Design, synthesis, and dopamine receptor modulating activity of diketopiperazine peptidomimetics of L-prolyl-L-leucylglycinamide [J].

Baures, PW ;

Ojala, WH ;

Costain, WJ ;

Ott, MC ;

Pradhan, A ;

Gleason, WB ;

Mishra, RK ;

Johnson, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (22) :3594-3600

[2] DESIGN, SYNTHESIS, X-RAY-ANALYSIS, AND DOPAMINE RECEPTOR-MODULATING ACTIVITY OF MIMICS OF THE C5 HYDROGEN-BONDED CONFORMATION IN THE PEPTIDOMIMETIC 2-OXO-3(R)-[(2(S)-PYRROLIDINYLCARBONYL)AMINO]-1-PYRROLIDINEACETAMIDE [J].

BAURES, PW ;

OJALA, WH ;

GLEASON, WB ;

MISHRA, RK ;

JOHNSON, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (22) :3677-3683

[3]

Baures PW, 1997, J PEPT RES, V50, P1

[4] CONFORMATIONAL-ANALYSIS OF CYCLIC HEXAPEPTIDES CONTAINING THE D-PRO-L-PRO SEQUENCE TO FIX BETA-TURN POSITIONS [J].

BEAN, JW ;

KOPPLE, KD ;

PEISHOFF, CE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5328-5334

[5] THE EFFECT OF MELANOTROPIN RELEASE INHIBITING FACTOR, ITS METABOLITES AND ANALOGS ON [H-3]SPIROPERIDOL AND [H-3]-LABELED APOMORPHINE BINDING-SITES [J].

BHARGAVA, HN .

GENERAL PHARMACOLOGY, 1983, 14 (06) :609-614

[6] PRO-D-NME-AMINO ACID AND D-PRO-NME-AMINO ACID - SIMPLE, EFFICIENT REVERSE-TURN CONSTRAINTS [J].

CHALMERS, DK ;

MARSHALL, GR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :5927-5937

[7] EFFECT OF L-PROLYL-L-LEUCYL-GLYCINAMIDE (PLG) ON NEUROLEPTIC-INDUCED CATALEPSY AND DOPAMINE-NEUROLEPTIC RECEPTOR BINDINGS [J].

CHIU, S ;

PAULOSE, CS ;

MISHRA, RK .

PEPTIDES, 1981, 2 (01) :105-111

[8] EFFECT OF CHRONIC TREATMENT WITH MORPHINE ON THE BINDING OF H-3-N-NORMAL-PROPYLNORAPOMORPHINE TO STRIATAL MEMBRANES OF RATS - INFLUENCE OF PROLYL-LEUCYL-GLYCINAMIDE [J].

DAS, S ;

BHARGAVA, HN .

PHARMACOLOGY, 1985, 31 (05) :241-247

[9]

EHRENSING RH, 1977, DIS NERV SYST, V38, P303

[10] DOPAMINE-RECEPTOR MODULATION BY A HIGHLY RIGID SPIRO BICYCLIC PEPTIDOMIMETIC OF PRO-LEU-GLY-NH2 [J].

GENIN, MJ ;

MISHRA, RK ;

JOHNSON, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (22) :3481-3483