Ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate

被引：1

作者：

Goncalves, Itamar Luis ^{[1
]}

Kagami, Luciano Porto ^{[1
]}

das Neves, Gustavo Machado ^{[1
]}

Rockenbach, Liliana ^{[1
]}

Davi, Leonardo ^{[1
]}

Soares, Alceu Felipe ^{[1
]}

Garcia, Solange Cristina ^{[2
]}

Eifler-Lima, Vera Lucia ^{[1
]}

机构：

[1] Univ Fed Rio Grande do Sul, Fac Farm, Lab Sintese Organ Med LaSOM, Ave Ipiranga 2752, BR-90610000 Porto Alegre, RS, Brazil

[2] Univ Fed Rio Grande do Sul, Fac Farm, Lab Toxicol LATOX, Ave Ipiranga 2752, BR-90610000 Porto Alegre, RS, Brazil

来源：

MOLBANK | 2018年 / 04期

关键词：

Biginelli reaction; dihydropyrimidin-2-thiones; synthesis; virtual screening; drug design; LaSOM; 282; ecto-5 '-nucleotidase;

D O I：

10.3390/M1029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/ thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methy1-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using a functionalized thiourea. In silico studies demonstrated that the compound title showed good potential for interacting with ecto-5'-nucleotidase, which has been considered as a target in designs for anti-cancer drugs.

引用

页数：4

共 50 条

[41] Synthesis, Crystal Structure and Antibacterial Activity of 2-(p-Tolyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole [J].

Liu, Xianping ;

He, Daohang .

ASIAN JOURNAL OF CHEMISTRY, 2014, 26 (11) :3216-3218

[42] Synthesis of N,6-diaryl-2-imino-4-methyl-3-cyano-1,2,3,6-tetrahydropyrimidine-5-carboxamides [J].

V. L. Gein ;

T. M. Zamaraeva ;

N. A. Buzmakova ;

A. Yu. Fedotov ;

L. F. Gein .

Russian Journal of General Chemistry, 2015, 85 :1540-1543

[43] Synthesis of 5-[2-(phenoxy)ethyl] derivatives of 6-methyluracil, 6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one, and 2-imino-6-methyl-2,3- dihydro-1H-pyrimidin-4-one [J].

Novikov M.S. ;

Ozerov A.A. ;

Sim O.G. .

Chemistry of Heterocyclic Compounds, 2005, 41 (8) :1036-1040

[44] Synthesis and structure of N,6-diaryl-4-methyl-2-cyanoimino-1,2,3,6-tetrahydropyrimidine-5-carboxamides [J].

Gein, V. L. ;

Zamaraeva, T. M. ;

Dmitriev, M. V. .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (02) :350-352

[45] Synthesis and structure of N,6-diaryl-4-methyl-2-cyanoimino-1,2,3,6-tetrahydropyrimidine-5-carboxamides [J].

V. L. Gein ;

T. M. Zamaraeva ;

M. V. Dmitriev .

Russian Journal of General Chemistry, 2017, 87 :350-352

[46] Synthesis, Characterization and In Silico Biological and Anticancer Activity of 3-(2-Fluorophenyl)-N-(4-Fluorophenyl)-7H-[1,2,4] Triazolo[3,4-b] [1,3,4] Thiadiazin-6-Amine [J].

Shah, Fahad Hassan ;

Vanjare, Balasaheb Daniyal ;

Kim, Song Ja .

CHIANG MAI JOURNAL OF SCIENCE, 2022, 49 (02) :377-386

[47] Synthesis and Crystal Structure of Ethyl 4-(2-Chloro-4-fluorophenyl)-6-hydroxy-3-oxo-1,3-dihydro-5-isobenzofurancarboxylate [J].

徐晓倩 ;

王晓奎 ;

杨世颖 ;

郑志兵 ;

赵国明 ;

李松 .

结构化学, 2010, 29 (01) :43-46

[48] Synthesis and Crystal Structure of Ethyl 4-(2-Chloro-4-fluorophenyl)-6-hydroxy-3oxo-1,3-dihydro-5-isobenzofurancarboxylate [J].

Xu Xiao-Qian ;

Wang Xiao-Kui ;

Yang Shi-Ying ;

Zheng Zhi-Bing ;

Zhao Guo-Ming ;

Li Song .

CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2010, 29 (01) :43-46

[49] Synthesis and Structural Characterization of Isostructural 4-(4-Aryl)-2-(5-(4-fluorophenyl)-3-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazoles [J].

Kariuki, Benson M. ;

Abdel-Wahab, Bakr F. ;

El-Hiti, Gamal A. .

CRYSTALS, 2021, 11 (07)

[50] One-pot synthesis of diethyl 4,4'-(1,4-phenylene)bis[6-(halomethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] and their bispyrrolocyclization [J].

Lebedyeva, Iryna O. ;

Povstyanoy, Mykhaylo V. ;

Povstyanoy, Vyacheslav M. ;

Panasyuk, Oleksandr G. ;

Guban, Evgen S. ;

Ryabitskii, Aleksey B. .

MONATSHEFTE FUR CHEMIE, 2010, 141 (09) :997-1000

← 1 2 3 4 5 →