Synthesis of novel Gn-RH analogues using Ugi-4MCR

被引:21
作者
Arabanian, Armin [1 ]
Mohammadnejad, Mahdieh [1 ]
Balalaie, Saeed [1 ]
Gross, Juergen H. [2 ]
机构
[1] KN Toosi Univ Technol, Peptide Chem Res Grp, Tehran, Iran
[2] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
Gn-RH analogues; 4-MCR Ugi reaction; Triptorelin and gonadorelin analogues; Ligation; GONADOTROPIN-RELEASING-HORMONE; PEPTIDE; LIGATION;
D O I
10.1016/j.bmcl.2008.11.111
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
An efficient method for the synthesis of some Gn-RH analogues based on Ugi reaction has been developed. Four-component reaction of N- and C-terminus peptides, aromatic aldehydes and isocyanides affords novel Gn-RH analogues derived from triptorelin and gonadorelin. All of the products were purified using preparative HPLC and the structures were assigned according to MALDI-mass spectrometry data. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.
引用
收藏
页码:887 / 890
页数:4
相关论文
共 21 条
[1]   PRESENCE OF LUTEINIZING-HORMONE-RELEASING HORMONE (LHRH) MESSENGER-RNA IN RAT SPLEEN LYMPHOCYTES [J].
AZAD, N ;
EMANUELE, NV ;
HALLORAN, MM ;
TENTLER, J ;
KELLEY, MR .
ENDOCRINOLOGY, 1991, 128 (03) :1679-1681
[2]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[3]   Convergent synthesis of peptide nucleic acids by native chemical Ligation [J].
Dose, C ;
Seitz, O .
ORGANIC LETTERS, 2005, 7 (20) :4365-4368
[4]  
ENGEL JB, 2005, GNRH ANALOGS HUMAN R, P35
[5]   Biology of the gonadotropin-releasing hormone system in gynecological cancers [J].
Gründker, C ;
Günthert, AR ;
Westphalen, S ;
Emons, G .
EUROPEAN JOURNAL OF ENDOCRINOLOGY, 2002, 146 (01) :1-14
[6]   Native chemical ligation at valine [J].
Haase, Christian ;
Rohde, Heike ;
Seitz, Oliver .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (36) :6807-6810
[7]   Extending the scope of native chemical peptide coupling [J].
Haase, Christian ;
Seitz, Oliver .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) :1553-1556
[8]   Recent development of peptide coupling reagents in organic synthesis [J].
Han, SY ;
Kim, YA .
TETRAHEDRON, 2004, 60 (11) :2447-2467
[9]   Via Ugi reactions to conformationally fixed cyclic peptides [J].
Hebach, C ;
Kazmaier, U .
CHEMICAL COMMUNICATIONS, 2003, (05) :596-597
[10]   Structure-activity study on the LH- and FSH-releasing and anticancer effects of gonadotropin-releasing hormone (GnRH)-III analogs [J].
Kovacs, Magdolna ;
Vincze, Borbala ;
Horvath, Judit E. ;
Seprodi, Janos .
PEPTIDES, 2007, 28 (04) :821-829