Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions

被引：12

作者：

Barreto, Angelica de Fatima S. ^{[1
]}

dos Santos, Veronica Alves ^{[1
]}

Andrade, Carlos Kleber Z. ^{[1
]}

机构：

[1] Univ Brasilia, Inst Quim, Lab Quim Metodol & Organ Sintet, CP 4478, BR-70910970 Brasilia, DF, Brazil

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 12卷

关键词：

acylhydrazino-peptomers; consecutive Ugi reactions; peptide-peptoid hybrid; peptomer; MULTICOMPONENT REACTIONS; CATALYZED HYDROLYSIS; PEPTOID LIBRARY; SERINE-PROTEASE; INHIBITORS; DESIGN; AZAPEPTIDES; PEPTIDES; PSEUDOPEPTIDES; DIVERSITY;

D O I：

10.3762/bjoc.12.285

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we describe a versatile approach for the synthesis of acylhydrazino-peptomers, a new class of peptidomimetics. The key idea in this approach is based on a simple route using a one-pot hydrazino-Ugi four-component reaction followed by a hydrazinolysis or hydrolysis reaction and subsequent hydrazino-Ugi reaction or classical Ugi reaction for the construction of acyclic acylhydrazino-peptomers. The consecutive multicomponent reactions produced a variety of acylhydrazino-peptomers in moderate to excellent yields (47-90%). These compounds are multifunctional intermediates that can be further functionalized to obtain new peptidomimetics with potential biological activity.

引用

页码：2865 / 2872

页数：8

共 65 条

[21] Microwave-assisted coupling with DIC/HOBt for the synthesis of difficult peptoids and fluorescently labelled peptides -: a gentle heat goes a long way [J].

Fara, MA ;

Díaz-Mochón, JJ ;

Bradley, M .

TETRAHEDRON LETTERS, 2006, 47 (06) :1011-1014

[22] Design and synthesis of macrocyclic peptomers as mimics of a quorum sensing signal from Staphylococcus aureus [J].

Fowler, Sarah A. ;

Stacy, Danielle M. ;

Blackwell, Helen E. .

ORGANIC LETTERS, 2008, 10 (12) :2329-2332

[23] Peptoids and Polypeptoids at the Frontier of Supra- and Macromolecular Engineering [J].

Gangloff, Niklas ;

Ulbricht, Juliane ;

Lorson, Thomas ;

Schlaad, Helmut ;

Luxenhofer, Robert .

CHEMICAL REVIEWS, 2016, 116 (04) :1753-1802

[24] AZAPEPTIDES, A NOVEL CLASS OF PEPTIDE ANALOGS [J].

GANTE, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1970, 9 (10) :813-&

[25]

GANTE J, 1989, SYNTHESIS-STUTTGART, P405

[26] Design and synthesis of hydrazinopeptides and their evaluation as human leukocyte elastase inhibitors [J].

Guy, L ;

Vidal, J ;

Collet, A ;

Amour, A ;

Reboud-Ravaux, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) :4833-4843

[27] An inhibitor of the Tat/TAR RNA interaction that effectively suppresses HIV-1 replication [J].

Hamy, F ;

Felder, ER ;

Heizmann, G ;

Lazdins, J ;

AboulEla, F ;

Varani, G ;

Karn, J ;

Klimkait, T .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (08) :3548-3553

[28] PEPTOIDS - A NEW APPROACH TO THE DEVELOPMENT OF PHARMACEUTICALS [J].

KESSLER, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (04) :543-544

[29] Hydrazinopeptide Motifs Synthesized via the Ugi Reaction: An Insight into the Secondary Structure [J].

Krasavin, Mikhail ;

Bushkova, Ekaterina ;

Parchinsky, Vladislav ;

Shumsky, Alexei .

SYNTHESIS-STUTTGART, 2010, (06) :933-942

[30] Diversity-oriented pyrazol-3-one synthesis based on hydrazinodipeptide-like units prepared via the Ugi reaction [J].

Lakontseva, Ekaterina ;

Krasavin, Mikhail .

TETRAHEDRON LETTERS, 2010, 51 (31) :4095-4099

← 1 2 3 4 5 6 7 →