New pyrrole-based amino acids for the synthesis of peptidomimetic constrained scaffolds

被引：23

作者：

Alongi, M ^{[1
]}

Minetto, G ^{[1
]}

Taddei, M ^{[1
]}

机构：

[1] Univ Siena, Dipartimento Farmaco Chim Tecnol, I-53100 Siena, Italy

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 41期

关键词：

Paal-Knorr reaction; cyclocondensation; microwaves; peptides;

D O I：

10.1016/j.tetlet.2005.07.155

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new family of pyrrole-based amino acids have been prepared through the microwave assisted Paal-Knorr reaction of 1-4 ketoesters derived from the corresponding beta-ketoester with a functional homologation. The carboxylic group is located in position 3 of the pyrrole, whereas the amino group, protected with the Cbz moiety, is present on the side chain in positions I or 2. These compounds were used to prepare constrained oligopeptides. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：7069 / 7072

页数：4

共 50 条

[41] Design, synthesis and molecular docking study of novel pyrrole-based α-amylase and α-glucosidase inhibitors
Jadhav, Nikhil C.
Pahelkar, Akshata R.
Desai, Neha V.
Telvekar, Vikas N.
MEDICINAL CHEMISTRY RESEARCH, 2017, 26 (10) : 2675 - 2691
[42] Synthesis of Pyrrole-Based Macrocycles as Molecular Probes for Multimodal Imaging Techniques: Recent Trends
Calvete, Mario J. F.
Pinto, Sara M.
CURRENT ORGANIC SYNTHESIS, 2017, 14 (05) : 704 - 714
[43] The enantioselective synthesis of conformationally constrained cyclic β-amino acids
Miller, JA
Nguyen, SBT
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2005, 2 (01) : 39 - 45
[44] Constrained amino acids. The synthesis of glutamine mimetics
Sabol, J. S.
Flynn, G. A.
Friedrich, D.
Huber, E. W.
Tetrahedron Letters, 38 (21):
[45] Constrained amino acids. The synthesis of glutamine mimetics
Sabol, JS
Flynn, GA
Friedrich, D
Huber, EW
TETRAHEDRON LETTERS, 1997, 38 (21) : 3687 - 3690
[46] Synthesis of chiral pyrazoles and isoxazoles as constrained amino acids
Falorni, M
Giacomelli, G
Spanedda, AM
TETRAHEDRON-ASYMMETRY, 1998, 9 (17) : 3039 - 3046
[47] Design and synthesis of conformationally constrained glycosylated amino acids
Koviach, JL
Chappell, MD
Halcomb, RL
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07): : 2318 - 2326
[48] SYNTHESIS AND COMPARATIVE STUDY OF TUBERCULOSTATIC ACTIVITY OF PYRROLE-BASED HYDRAZONES RELATED TO STRUCTURAL VARIATIONS
Georgieva, M.
Bijev, A.
Prodanova, P.
PHARMACIA, 2010, 57 (1-4) : 3 - 14
[49] Synthesis and characterization of constrained peptidomimetic dipeptidyl peptidase IV inhibitors: Amino-lactam boroAlanines
Lai, Jack H.
Wu, Wengen
Zhou, Yuhong
Maw, Hlaing H.
Liu, Yuxin
Milo, Lawrence J.
Poplawski, Sarah E.
Henry, Gillian D.
Sudmeier, James L.
Sanford, David G.
Bachovchin, William W.
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (10) : 2391 - 2398
[50] Tetrahydrofuran-based amino acids as library scaffolds
Edwards, AA
Ichihara, O
Murfin, S
Wilkes, R
Whittaker, M
Watkin, DJ
Fleet, GWJ
JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (02): : 230 - 238

← 1 2 3 4 5 →