Synthesis and biological evaluation of novel imidazole-containing macrocycles

被引：19
|
作者：
Nshimyumukiza, Prosper [1 ,2 ]
Van Den Berge, Emilie [1 ]
Delest, Bruno [1 ,2 ]
Mijatovic, Tatjana [3 ]
Kiss, Robert [3 ]
Marchand-Brynaert, Jacqueline [1 ]
Robiette, Raphael [1 ]
机构：
[1] Catholic Univ Louvain, Inst Condensed Matter & Nanosci, B-1348 Louvain, Belgium
[2] Unibioscreen SA, B-1070 Brussels, Belgium
[3] Univ Libre Bruxelles, Inst Pharm, B-1050 Brussels, Belgium
来源：
TETRAHEDRON | 2010年 / 66卷 / 25期
关键词：
Central nervous system; Conformational flexibility; Imidazole; Inflammation; Macrocycles; RECEPTORS; AGONISTS; DESIGN;
D O I：
10.1016/j.tet.2010.04.070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new family of compounds made of a 5-aryl-1H-imidazole motif included in a macrocycle has been designed and synthesized. The synthesis of the imidazole core makes use of our previously developed method for the regioselective preparation of 1,2,5-trisubstituted imidazoles while the construction of the macrocycle is based on a three steps sequence: SNAr, Suzuki coupling, and RCM reaction. Biological evaluation of synthesized imidazole-containing macrocycles revealed that they display actual binding activity toward A(3) adenosine (h) receptor, dopamine D-1 (h) receptor, chloride channel (GABA-gated), and choline transporter (h) CHT1. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4515 / 4520
页数：6
相关论文
共 50 条
  • [1] SYNTHESIS OF MULTIDENTATE IMIDAZOLE-CONTAINING MACROCYCLES
    CHOI, YD
    STREET, JP
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04): : 1258 - 1262
  • [2] Synthesis of imidazole-containing analogues of farnesyl pyrophosphate and evaluation of their biological activity on protein farnesyltransferase
    Coudray, Laetitia
    de Figueiredo, Renata Marcia
    Duez, Stephanie
    Cortial, Sylvie
    Dubois, Joelle
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2009, 24 (04) : 972 - 985
  • [3] Planar Chirality of Imidazole-Containing Macrocycles - Understanding and Tuning Atropisomerism
    Van den Berge, Emilie
    Pospisil, Jiri
    Trieu-Van, Tran
    Collard, Laurent
    Robiette, Raphael
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (33) : 6649 - 6655
  • [4] Novel imidazole-containing thioxanthone derivative for photopolymerization
    Qiu, Jun
    Wei, Jun
    JOURNAL OF POLYMER RESEARCH, 2014, 21 (08)
  • [5] Novel imidazole-containing thioxanthone derivative for photopolymerization
    Jun Qiu
    Jun Wei
    Journal of Polymer Research, 2014, 21
  • [6] Synthesis and Characterization of an Imidazole-Containing Pyrene π-System
    Liu, Yulong
    Gao, Zhao
    Wang, Zhiming
    Feng, Cunfang
    Shen, Fangzhong
    Lu, Ping
    Ma, Yuguang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (32) : 7267 - 7271
  • [7] Superacid-promoted synthesis of imidazole-containing spirocycles
    Ferreira, Jeffrey C.
    Klumpp, Douglas A.
    TETRAHEDRON, 2025, 176
  • [8] Synthesis of imidazole-containing ligands and studies on metal complexes
    Yamagiwa, Y
    Koreishi, Y
    Kiyozumi, S
    Kobayashi, M
    Kamikawa, T
    Tsukino, M
    Goi, H
    Yamamoto, M
    Munakata, M
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (11) : 3317 - 3323
  • [9] Synthesis and evaluation of in vitro and in vivo trypanocidal properties of a new imidazole-containing nitrophthalazine derivative
    Olmo, Francisco
    Gomez-Contreras, Fernando
    Navarro, Pilar
    Marin, Clotilde
    Yunta, Maria J. R.
    Cano, Carmen
    Campayo, Lucrecia
    Martin-Oliva, David
    Jose Rosales, Maria
    Sanchez-Moreno, Manuel
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 106 : 106 - 119
  • [10] Synthesis of imidazole-containing analogues of farnesyl pyrophosphate and evaluation of their biological activity on protein farnesyltransferase (vol 24, pg 972, 2009)
    Coudray, Laetitia
    de Figueiredo, Renata Marcia
    Duez, Stephanie
    Cortial, Sylvie
    Dubois, Joelle
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2010, 25 (04) : 596 - 598
12345