Neutral urea-based receptors for phosphates: synthesis and spectrophotometric studies

被引：6
|
作者：
Formica, Mauro [1 ]
Fusi, Vieri [1 ]
Giorgi, Luca [1 ]
Piersanti, Giovanni [2 ]
Retini, Michele [2 ]
Zappia, Giovanni [2 ]
机构：
[1] Univ Urbino Carlo Bo, Chem Sect, Dept Pure & Appl Sci, Pzza Rinascimento 6, I-61029 Urbino, Italy
[2] Univ Urbino Carlo Bo, Dept Biomol Sci, Pzza Rinascimento 6, I-61029 Urbino, Italy
来源：
TETRAHEDRON | 2016年 / 72卷 / 44期
关键词：
BODIPY; Coumarin; Fluorescence; Urea; Phosphates; ANIONS; THIOUREA; FLUORESCENCE; DERIVATIVES; BINDING; BODIPY; TRACKING; DONOR; DYES;
D O I：
10.1016/j.tet.2016.09.042
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of five fluorescent ligands (L1-L5) for anions were designed and synthesized. Urea, thiourea, and cyanoguanidine moieties were chosen as the binding groups, while 3,5-bis(trifluoromethyl)phenyl, coumarin, and BODIPY were used as the chromophores. The cyanoguanidines L3-L5 were promptly synthesized from corresponding thioureas using EDCI followed by reaction with cyanamide in the presence of triethylamine. The absorption and emission properties of the ligands L1-L5 were studied in CH3CN; their coordination properties towards phosphate, pyrophosphate, and hydroxide anions, together with binding constants were evaluated. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7039 / 7049
页数：11
相关论文
共 50 条
  • [31] Design, synthesis, and biological evaluation of urea-based ROCK2 inhibitors
    Wang, Linan
    Qi, Junhui
    Fan, Meixia
    Yao, Lei
    CHEMICAL BIOLOGY & DRUG DESIGN, 2021, 98 (06) : 969 - 978
  • [32] Synthesis and in vitro and in vivo evaluation of urea-based PSMA inhibitors with increased lipophilicity
    Wirtz, Martina
    Schmidt, Alexander
    Schottelius, Margret
    Robu, Stephanie
    Guenther, Thomas
    Schwaiger, Markus
    Wester, Hans-Juergen
    EJNMMI RESEARCH, 2018, 8
  • [33] Design, synthesis and biological evaluation of urea-based benzamides derivatives as HDAC inhibitors
    Yong Zhu
    Xin Chen
    Ting Ran
    Jiaqi Niu
    Shuang Zhao
    Tao Lu
    Weifang Tang
    Medicinal Chemistry Research, 2017, 26 : 2879 - 2888
  • [34] Synthesis and in vitro and in vivo evaluation of urea-based PSMA inhibitors with increased lipophilicity
    Martina Wirtz
    Alexander Schmidt
    Margret Schottelius
    Stephanie Robu
    Thomas Günther
    Markus Schwaiger
    Hans-Jürgen Wester
    EJNMMI Research, 8
  • [35] 1,3-Phenyl linked urea-based receptors for anions and the facile cyclization to imidazolidinedione
    Haridas, V.
    Sadanandan, Sandhya
    Hundal, Geeta
    Suresh, Cherumattathu H.
    TETRAHEDRON LETTERS, 2012, 53 (41) : 5523 - 5527
  • [36] Synthesis and binding studies of hydrogen bonding urea receptors
    Cabrera, SF
    Govindaraju, S
    Bell, TW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3414 - U3414
  • [37] N-Alkyl Carbamoylimidazoles as Versatile Synthons for the Synthesis of Urea-Based PSMA Inhibitors
    Gade, Narendar Reddy
    Kaur, Jatinder
    Bhardwaj, Atul
    Ebrahimi, Edris
    Dufour, Jennifer
    Wuest, Melinda
    Wuest, Frank
    ACS MEDICINAL CHEMISTRY LETTERS, 2023, 14 (07): : 943 - 948
  • [38] Palladium catalysts supported on biodegradable urea-based polymers in synthesis with CO - Part B
    Markovic, Martin
    Lopatka, Pavol
    Koos, Peter
    Sotak, Tomas
    Haz, Ales
    Gracza, Tibor
    Ley, Steven V.
    Kralik, Milan
    CATALYSIS TODAY, 2024, 440
  • [39] A novel series of urea-based peptidomimetic calpain inhibitors
    Sanders, ML
    Donkor, IO
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (07) : 1965 - 1968
  • [40] Selective Binding of Spherical and Linear Anions by Tetraphenyl(thio)urea-Based Dihomooxacalix[4]arene Receptors
    Teixeira, Filipa A.
    Marcos, Paula M.
    Ascenso, Jose R.
    Brancatelli, Giovanna
    Hickey, Neal
    Geremia, Silvano
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (21): : 11383 - 11390
12345