From cyclic dehydrodipeptides to uncommon acyclic peptide mimetics

被引：7
|
作者：
Francisco Gonzalez, Juan [1 ]
de la Cuesta, Elena [1 ]
Avendano, Carmen [1 ]
机构：
[1] Univ Complutense Madrid, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 38期
关键词：
D O I：
10.1016/j.tetlet.2006.07.095
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1-Acetyl-3 -arylmethylene-2,5-piperazinediones gave N-3-arylpyruvylamino esters by acid-promoted alcoholysis under thermal conditions or microwave irradiation. Compounds obtained from 1-acetyl-3-(o-nitro)arylmethylene-2,5-piperazinediones gave, after reduction of the nitro group and spontaneous cyclization, N-2-indolylcarbonylamino acid derivatives. A similar alcoholysis/reduction sequence applied to dehydrodipeptides bearing a 3(4)-nitroaryl substituent gave N-3(4)-aminophenyi-alpha-ketopropionylamino acid derivatives. Coupling of the free amino group with Boc-protected amino acids gave tripeptide mimetics with a 6-aminoindole-2-carboxylic or a 3(4)-aminophenyl-alpha-ketopropionic acid as the second residue. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6711 / 6714
页数：4
相关论文
共 50 条
  • [1] Unexpected variations in the reactivities and selectivities of acyclic and cyclic dehydrodipeptides in Diels-Alder reactions
    Burkett, BA
    Chai, CLL
    Hockless, DCR
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1998, 51 (11) : 993 - 997
  • [2] Synthesis of cyclic (α2β)-tripeptides as potential peptide turn mimetics
    Wels, B
    Kruijtzer, JAW
    Liskamp, RMJ
    ORGANIC LETTERS, 2002, 4 (13) : 2173 - 2176
  • [3] Conformationally constrained cyclic mimetics of protein and peptide surfaces.
    Wong, AK
    Reid, RC
    Abbenante, J
    Fairlie, DP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 388 - ORGN
  • [4] Synthesis of Cyclic Peptide Mimetics by the Successive Ring Expansion of Lactams
    Stephens, Thomas C.
    Lodi, Mahendar
    Steer, Andrew M.
    Lin, Yun
    Gill, Matthew T.
    Unsworth, William P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (54) : 13314 - 13318
  • [5] DEVELOPMENT OF ANTIBODY MIMETICS BASED ON A CYCLIC HEXA-PEPTIDE SCAFFOLD
    Gopalakrishnan, R.
    Heinis, C.
    JOURNAL OF PEPTIDE SCIENCE, 2014, 20 : S47 - S47
  • [6] Computational screening of branched cyclic peptide motifs as potential enzyme mimetics
    Stavrakoudis, A
    Makropoulou, S
    Tsikaris, V
    Sakarellos-Daitsiotis, M
    Sakarellos, C
    Demetropoulos, IN
    JOURNAL OF PEPTIDE SCIENCE, 2003, 9 (03) : 145 - 155
  • [7] Cyclic thioether peptide mimetics as VCAM-VLA-4 antagonists
    Fotouhi, N
    Joshi, P
    Tilley, JW
    Rowan, K
    Schwinge, V
    Wolitzky, B
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (11) : 1167 - 1169
  • [8] α-Turn Mimetics: Short Peptide α-Helices Composed of Cyclic Metallopentapeptide Modules
    Fairlie, D.P. (d.fairlie@imb.uq.edu.au), 1600, American Chemical Society (126):
  • [9] α-turn mimetics:: short peptide α-Helices composed of cyclic metallopentapeptide modules
    Kelso, MJ
    Beyer, RL
    Hoangt, HN
    Lakdawala, AS
    Snyder, JP
    Oliver, WV
    Robertson, TA
    Appleton, TG
    Fairlie, DP
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) : 4828 - 4842
  • [10] ANTITHROMBOTIC AGENTS - FROM RGD TO PEPTIDE MIMETICS
    OJIMA, I
    CHAKRAVARTY, S
    DONG, Q
    BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (04) : 337 - 360
12345