Solution and solid-supported synthesis of 3,4,5-trisubstituted 1,2,4-triazole-based peptidomimetics

被引:65
作者
Boeglin, D
Cantel, S
Heitz, A
Martinez, J
Fehrentz, JA
机构
[1] Univ Montpellier I, LAPP, Fac Pharm, CNRS,UMR 5810, F-34093 Montpellier 5, France
[2] Univ Montpellier 2, F-34093 Montpellier 5, France
关键词
D O I
10.1021/ol035778e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3,4,5-Trisubstituted 1,2,4-triazoles were synthesized in solution from various thioamides and hydrazides in smooth experimental conditions leading to peptidomimetic scaffolds. This strategy was found to be compatible with the usual peptide synthesis protecting groups. This methodology was then applied on solid support by anchoring alpha-amino acids through their amino function to an activated carbonate resin.
引用
收藏
页码:4465 / 4468
页数:4
相关论文
共 29 条
[1]   Reactions of thioamides with metal carboxylates in organic media [J].
Avalos, M ;
Babiano, R ;
Cintas, P ;
Duran, CJ ;
Higes, FJ ;
Jimenez, JL ;
Lopez, I ;
Palacios, JC .
TETRAHEDRON, 1997, 53 (42) :14463-14480
[2]   Efficient solid-phase synthesis of 4,5-dihydro-1,2,4-triazin-6(1H)-ones [J].
Boeglin, D ;
Cantel, S ;
Martinez, J ;
Fehrentz, JA .
TETRAHEDRON LETTERS, 2003, 44 (03) :459-462
[3]   SYNTHESIS OF 1,2,4-OXADIAZOLE-DERIVED, 1,3,4-OXADIAZOLE-DERIVED, AND 1,2,4-TRIAZOLE-DERIVED DIPEPTIDOMIMETICS [J].
BORG, S ;
ESTENNEBOUHTOU, G ;
LUTHMAN, K ;
CSOREGH, I ;
HESSELINK, W ;
HACKSELL, U .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3112-3120
[4]   NONPEPTIDE RENIN INHIBITORS WITH GOOD INTRADUODENAL BIOAVAILABILITY AND EFFICACY IN DOG [J].
BOYD, SA ;
FUNG, AKL ;
BAKER, WR ;
MANTEI, RA ;
STEIN, HH ;
COHEN, J ;
BARLOW, JL ;
KLINGHOFER, V ;
WESSALE, JL ;
VERBURG, KM ;
POLAKOWSKI, JS ;
ADLER, AL ;
CALZADILLA, SV ;
KOVAR, P ;
YAO, ZL ;
HUTCHINS, CW ;
DENISSEN, JF ;
GRABOWSKI, BA ;
CEPA, S ;
HOFFMAN, DJ ;
GARREN, KW ;
KLEINERT, HD .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (19) :2991-3007
[5]   BENZOPYRAN POTASSIUM CHANNEL ACTIVATORS RELATED TO CROMAKALIM - HETEROCYCLIC AMIDE REPLACEMENTS AT POSITION-4 [J].
BURRELL, G ;
EVANS, JM ;
HADLEY, MS ;
HICKS, F ;
STEMP, G .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (11) :1285-1290
[6]  
BUZYKIN BI, 1993, SYNTHESIS-STUTTGART, P59
[7]   1-Alkyl-3-amino-5-aryl-1H-1,2,4]triazoles:: Novel synthesis via cyclization of N-acyl-S-methylisothioureas with alkylhydrazines and their potent corticotropin-releasing factor-1 (CRF1) receptor antagonist activities [J].
Chen, C ;
Dagnino, R ;
Huang, CQ ;
McCarthy, JR ;
Grigoriadis, DE .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (24) :3165-3168
[8]   STUDIES ON AMINO-ACIDS AND PEPTIDES .1. SYNTHESIS OF N-BENZYLOXYCARBONYLENDOTHIODIPEPTIDE ESTERS [J].
CLAUSEN, K ;
THORSEN, M ;
LAWESSON, SO .
TETRAHEDRON, 1981, 37 (21) :3635-3639
[9]   1,2,4-triazolo mercapto and aminonitriles as potent antifungal agents [J].
Collin, X ;
Sauleau, A ;
Coulon, J .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (15) :2601-2605
[10]  
CONDE S, 1974, SYNTHESIS-STUTTGART, P28