Triproline analogues of Pro-Leu-Gly-NH2 with Pro/Leu and Pro/Phe chimeric amino acids in position 2

被引:17
作者
Evans, MC [1 ]
Johnson, RL [1 ]
机构
[1] Univ Minnesota, Dept Med Chem, Minneapolis, MN 55455 USA
关键词
chimeric amino acids; triproline analogue; proline-leucine;
D O I
10.1016/S0040-4020(00)00887-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of the cis- and trans-isomers of the proline-leucine (3-i-Pr-Pro) and proline-phenylalanine (S-Ph-Pro) chimeric amino acids was accomplished by intramolecular reductive-cycloalkylation of the appropriate azido-olefin. These chimeric amino acids were incorporated into the triprolyl analogues of Pro-Leu-Gly-NH2: Pro-cia 3-i-Pr-Pro-Pro-NH2 (3), Pro-trans-3-i-Pr-Pro-Pro-NH2 (4), Pro-cis-3-Ph-Pro-Pro-NH2 (5), Pro-trans-3-Ph-Pro-Pro-NH2 (6). (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9801 / 9808
页数:8
相关论文
共 27 条
[1]   Synthesis and dopamine receptor modulating activity of unsubstituted and substituted triproline analogues of L-prolyl-L-leucyl-glycinamide (PLG) [J].
Baures, PW ;
Pradhan, A ;
Ojala, WH ;
Gleason, WB ;
Mishra, RK ;
Johnson, RL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (16) :2349-2352
[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]  
BROWN HC, 1975, ORGANIC SYNTHESIS VI, P28
[4]   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
[5]   CONFORMATIONALLY CONSTRAINED AMINO-ACIDS - SYNTHESIS AND OPTICAL RESOLUTION OF 3-SUBSTITUTED PROLINE DERIVATIVES [J].
CHUNG, JYL ;
WASICAK, JT ;
ARNOLD, WA ;
MAY, CS ;
NADZAN, AM ;
HOLLADAY, MW .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :270-275
[6]  
Damour D, 1999, SYNLETT, P786
[7]   SYNTHESIS OF THE CYCLIC HEXAPEPTIDE ECHINOCANDIN-D - NEW APPROACHES TO THE ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY ALPHA-AMINO-ACIDS [J].
EVANS, DA ;
WEBER, AE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7151-7157
[8]   THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA ;
DOROW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030
[9]   REACTION OF ARYLSULFONYL AZIDES WITH N-METHYLINDOLE [J].
HARMON, RE ;
WELLMAN, G ;
GUPTA, SK .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) :11-16
[10]   DOPAMINE RECEPTOR MODULATION BY PRO-LEU-GLY-NH2 ANALOGS POSSESSING CYCLIC AMINO-ACID-RESIDUES AT THE C-TERMINAL POSITION [J].
JOHNSON, RL ;
RAJAKUMAR, G ;
MISHRA, RK .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (10) :2100-2104