A facile route for the synthesis of novel S-linked 1,3,5-triazine tethered peptidomimetics

被引:9
作者
Krishnamurthy, Muniyappa [1 ]
Basavaprabhu [1 ]
Sharanabai, K. M. [1 ]
Sureshbabu, Vommina V. [1 ]
机构
[1] Bangalore Univ, Dept Studies Chem, Peptide Res Lab, Bangalore 560001, Karnataka, India
关键词
N-alpha-protected amino alkyl isothiouronium salts; Amino acid ester; Formaldehyde; Dehydrocyclization; CONVENIENT SYNTHESIS; CHEMISTRY; DESIGN; ACIDS; ANALOGS; SERIES; PHASE;
D O I
10.1016/j.tetlet.2014.08.075
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient one-pot synthesis of N-alpha-protected S-linked 1,3,5-triazine tethered peptidomimetics is described. The protocol involves a three-component condensation reaction employing N-alpha-protected amino alkyl isothiouronium salt, formaldehyde and amino acid ester or aryl amine as reactants. Various aryl amines with substitutions and amino acids with simple as well as bifunctional side chains were employed to obtain triazine tethered peptidomimetics in good yield. (C) 2014 Published by Elsevier Ltd.
引用
收藏
页码:5609 / 5612
页数:4
相关论文
共 43 条
  • [1] Heterocyclic-based peptidomimetics
    Abell, AD
    [J]. LETTERS IN PEPTIDE SCIENCE, 2001, 8 (3-5): : 267 - 272
  • [2] Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions
    Angell, Yu L.
    Burgess, Kevin
    [J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) : 1674 - 1689
  • [3] Triazine Compounds as Antagonists at Bv8-Prokineticin Receptors
    Balboni, Gianfranco
    Lazzari, Ilaria
    Trapella, Claudio
    Negri, Lucia
    Lattanzi, Roberta
    Giannini, Elisa
    Nicotra, Annalisa
    Melchiorri, Pietro
    Visentin, Sergio
    De Nuccio, Chiara
    Salvadori, Severo
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (23) : 7635 - 7639
  • [4] Banerjee S., 2013, J. Adv. Pharm. Educ. Res., V3, P494
  • [5] Solution and solid-supported synthesis of 3,4,5-trisubstituted 1,2,4-triazole-based peptidomimetics
    Boeglin, D
    Cantel, S
    Heitz, A
    Martinez, J
    Fehrentz, JA
    [J]. ORGANIC LETTERS, 2003, 5 (23) : 4465 - 4468
  • [6] Brown E. D., 1979, Eur. Pat. Appl. EP, Patent No. [EP 300756, 300756]
  • [7] A trinuclear copper(II) complex of 2,4,6-tris(di-2-pyridylamine)-1,3,5-triazine shows prominent DNA cleavage activity
    Chen, Jingwen
    Wang, Xiaoyong
    Shao, Ying
    Zhu, Jianhui
    Zhu, Yangguang
    Li, Yizhi
    Xu, Qiang
    Guo, Zijian
    [J]. INORGANIC CHEMISTRY, 2007, 46 (08) : 3306 - 3312
  • [8] Coats S. J., 2006, [No title captured], Patent No. [WO2006104713, 2006104713, WO 2006104713]
  • [9] Farmer P.S., 1980, Drug Design, V10, P119
  • [10] SPECULATIONS ON THE DESIGN OF NON-PEPTIDIC PEPTIDOMIMETICS
    FARMER, PS
    ARIENS, EJ
    [J]. TRENDS IN PHARMACOLOGICAL SCIENCES, 1982, 3 (09) : 362 - 365