Thiacalix[4]arene phosphoric acids. Synthesis, structure, and inhibition of glutathione S-transferases

被引：2

作者：

Silenko, Oleg ^{[1
]}

Cherenok, Serhii ^{[1
]}

Shulha, Yurii ^{[2
]}

Kobzar, Oleksandr ^{[2
]}

Rusanov, Eduard ^{[1
]}

Karpichev, Yevgen ^{[3
]}

Vovk, Andriy ^{[2
]}

Kalchenko, Vitaly ^{[1
]}

机构：

[1] NAS Ukraine, Inst Organ Chem, Kiev 94, Ukraine

[2] NAS Ukraine, Inst Bioorgan Chem & Petrochem, Kiev 94, Ukraine

[3] Tallinn Univ Technol, Tallinn, Estonia

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2022年 / 197卷 / 5-6期

关键词：

thiacalix[4]arenes; phosphoric acid; synthesis; X-ray analysis; inhibitor; glutathione S-transferase; PROTEIN;

D O I：

10.1080/10426507.2021.2011877

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Regioselective phosphorylation of tetrahydroxythiacalix[4] arenes by diethyl chlorophosphate in the presence of triethylamine or by the system diethylphosphite/carbon tetrachloride/triethylamine gave ethyl esters of thiacalix[4] arene monophosphoric or thiacalix[4] arene diphosphoric acids, respectively. The obtained esters were converted with quantitative yields into corresponding free acids by sequential treatment with trimethylbromosilane and methanol. The thiacalix[4] arene diphosphoric acids were evaluated in vitro as inhibitors of glutathione S-transferases.

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收藏

页码：538 / 541

页数：4

相关论文

共 15 条

[1] Calix[4]arene-α-hydroxyphosphonic acids. Synthesis, stereochemistry, and inhibition of glutathione S-transferase [J].

Cherenok, Sergiy O. ;

Yushchenko, Olexander A. ;

Tanchuk, Vsevolod Yu. ;

Mischenko, Iryna M. ;

Samus, Nataliya V. ;

Ruban, Olexander V. ;

Matvieiev, Yuriy I. ;

Karpenko, Julia A. ;

Kukhar, Valery P. ;

Vovk, Andriy I. ;

Kalchenko, Vitaly I. .

ARKIVOC, 2012, :278-298

[2] Moulding calixarenes for biomacromolecule targeting [J].

Giuliani, Marta ;

Morbioli, Ilaria ;

Sansone, Francesco ;

Casnati, Alessandro .

CHEMICAL COMMUNICATIONS, 2015, 51 (75) :14140-14159

[3]

Gutsche C., 1998, CALIXARENES REVISITE

[4] The mercapturic acid pathway [J].

Hanna, Patrick E. ;

Anders, M. W. .

CRITICAL REVIEWS IN TOXICOLOGY, 2019, 49 (10) :819-929

[5] (Thia)calixarenephosphonic Acids as Potent Inhibitors of the Nucleic Acid Chaperone Activity of the HIV-1 Nucleocapsid Protein with a New Binding Mode and Multitarget Antiviral Activity [J].

Humbert, Nicolas ;

Kovalenko, Lesia ;

Saladini, Francesco ;

Giannini, Alessia ;

Pires, Manuel ;

Botzanowski, Thomas ;

Cherenok, Sergiy ;

Boudier, Christian ;

Sharma, Kamal K. ;

Real, Eleonore ;

Zaporozhets, Olga A. ;

Cianferani, Sarah ;

Seguin-Devaux, Carole ;

Poggialini, Federica ;

Botta, Maurizio ;

Zazzi, Maurizio ;

Kalchenko, Vitaly, I ;

Mori, Mattia ;

Mely, Yves .

ACS INFECTIOUS DISEASES, 2020, 6 (04) :687-702

[6]

MCKENNA CE, 1977, TETRAHEDRON LETT, P155

[7] Biomedical Applications of Calixarenes: State of the Art and Perspectives [J].

Pan, Yu-Chen ;

Hu, Xin-Yue ;

Guo, Dong-Sheng .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (06) :2768-2794

[8] Phosphonic acid: preparation and applications [J].

Sevrain, Charlotte M. ;

Berchel, Mathieu ;

Couthon, Helene ;

Jaffres, Paul-Alain .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 :2186-2213

[9] Phosphonate monoesters on a thiacalix[4]arene framework as potential inhibitors of protein tyrosine phosphatase 1B [J].

Trush, Viacheslav V. ;

Kharchenko, Sergiy G. ;

Tanchuk, Vsevolod Yu. ;

Kalchenko, Vitaly I. ;

Vovk, Andriy I. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (33) :8803-8806

[10] Calix[4]arene methylenebisphosphonic acids as inhibitors of protein tyrosine phosphatase 1B [J].

Trush, Viacheslav V. ;

Cherenok, Sergiy O. ;

Tanchuk, Vsevolod Yu. ;

Kukhar, Valery P. ;

Kalchenko, Vitaly I. ;

Vovk, Andriy I. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (20) :5619-5623