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
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
收藏
页数:4
相关论文
共 50 条
[21]   A GREENER CHEMISTRY APPROACH FOR SYNTHESIS OF 4-(4-HYDROXYPHENYL)-6-METHYL- 2-OXO-1,2,3,4 TETRAHYDROPYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER [J].
Jagwani, D. ;
Joshi, P. .
INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2015, 6 (02) :783-790
[22]   Synthesis, Crystal Structure, and DFT Study of a New Compound 6-(2-Fluorophenyl)-N-(p-Tolyl)Imidazo[1,2-A]Pyridine-2-Carboxamide [J].
Qin, Y. ;
Long, D. ;
Zhu, X. ;
Zhou, Z. ;
Chai, H. ;
Zhao, C. .
JOURNAL OF STRUCTURAL CHEMISTRY, 2019, 60 (12) :1917-1924
[23]   Synthesis and crystal structure of 5-(p-tolyl)-4-[2-(2,4-dichlorophenoxy)acetamido]-1,2,4-triazole-3-thione ethyl acetate solvate [J].
Xue Si-Jia ;
Xiang Chang-Sheng ;
Yu Song-Rui ;
Sun Jin-Feng ;
Chai An ;
Shen Jian .
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2008, 27 (04) :389-393
[24]   Synthesis, Crystal Structure, and DFT Study of a New Compound 6-(2-Fluorophenyl)-N-(p-Tolyl)Imidazo[1,2-A]Pyridine-2-Carboxamide [J].
Y. Qin ;
D. Long ;
X. Zhu ;
Z. Zhou ;
H. Chai ;
C. Zhao .
Journal of Structural Chemistry, 2019, 60 :1917-1924
[25]   Synthesis and Crystal Structure of 5-(p-Tolyl)-4-[2-(2,4-dichlorophenoxy)acetamido]-1,2,4-triazole-3-thione Ethyl Acetate Solvate [J].
薛思佳 ;
向长胜 ;
吁松瑞 ;
孙晋峰 ;
柴安 ;
沈健 .
Chinese Journal of Structural Chemistry, 2008, (04) :389-393
[26]   Synthesis and antibacterial activities of novel pyrimidines derived from 2-oxo (or thioxo)-4-phenyl-5-carbethoxy-6-methyl-1,2,3,4-tetrahydropyrimidine [J].
Foroughifar, N ;
Mobinikhaledi, A .
ASIAN JOURNAL OF CHEMISTRY, 2002, 14 (02) :614-618
[27]   Synthesis and crystal structure of ethyl 4-(3,4-methylenedioxylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate under microwave irradiation [J].
Tu, SJ ;
Gao, Y ;
Zhou, JF ;
Shi, DQ ;
Wang, XS ;
Zhuang, QY .
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2002, 21 (06) :609-612
[28]   Synthesis and Crystal Structure of Ethyl 4-(3,4-Methylenedioxylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate under Microwave Irradiation [J].
TU ShuJiang GAO Yuan ZHOU JianFeng SHI DaQing WANG XiangShan ZHUANG QiYaDepartment of Chemistry Xuzhou Normal University Xuzhou Jiangsu ChinaDepartment of Chemistry Shenzhen University Shenzhen China Department of Chemistry Huaiyin Teacher College Huaiyin Jiangsu China .
结构化学, 2002, (06) :609-612
[29]   Synthesis and antimicrobial activity of N,6-diaryl-4-methyl-2-thioxo-1,2,3,6-tetrahydropyrimidine-5-carboxamides [J].
V. L. Gein ;
I. V. Kholkin ;
T. M. Zamaraeva ;
E. V. Voronina ;
M. I. Vakhrin .
Pharmaceutical Chemistry Journal, 2012, 46 :114-116
[30]   Synthesis and antimicrobial activity of N,6-diaryl-4-methyl-2-thioxo-1,2,3,6-tetrahydropyrimidine-5-carboxamides [J].
Gein, V. L. ;
Kholkin, I. V. ;
Zamaraeva, T. M. ;
Voronina, E. V. ;
Vakhrin, M. I. .
PHARMACEUTICAL CHEMISTRY JOURNAL, 2012, 46 (02) :114-116