Synthesis, Crystal Structure and Antitumor Activity of (E)-N-(4-Fluorobenzylidene)-3-(methylthio)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-amine

被引：0

作者：

Lin Wei-Yuan ^{[1
]}

Yang Fang ^{[1
]}

Duan An-Na ^{[1
]}

You Wen-Wei ^{[1
]}

Zhao Pei-Liang ^{[1
]}

机构：

[1] Southern Med Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab New Drug Screening, Guangzhou 510515, Guangdong, Peoples R China

来源：

CHINESE JOURNAL OF STRUCTURAL CHEMISTRY | 2018年 / 37卷 / 10期

基金：

中国国家自然科学基金;

关键词：

(E)-N-(4-fluorobenzylidene)-3-(methylthio)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-amine; synthesis; crystal structure; antitumor activity; ONE-POT SYNTHESIS; BIOLOGICAL EVALUATION; ANTIPROLIFERATIVE ACTIVITY; SCHIFF-BASES; DESIGN; DOCKING;

D O I：

10.14102/j.cnki.0254-5861.2011-1967

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The crystal structure of the title compound (E)-N-(4-fluorobenzylidene)-3-(methylthio)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-amine (C19H19FN4O3S, M-r = 402.44) was synthesized, and its structure was characterized by H-1-NMR, C-13-NMR, ESI-MS and single-crystal X-ray diffraction. The crystal belongs to the triclinic system, space group P (1) over bar with a = 9.228(13), b = 10.364(14), c = 10.641(14) angstrom, alpha = 85.323(3), beta = 75.172(2), gamma = 80.903(3)degrees, mu = 0.20 mm(-1), M-r = 402.44, V = 970.64(10) angstrom(3), Z = 2, D-c = 1.377 g/cm(3), F(000) = 420, R = 0.0484 and wR = 0.1474 for 3181 observed reflections with I > 2 sigma(I). In addition, the preliminary bioassay indicated that the title compound 5 exhibits better inhibitory activity against Hela than 5-fluorouracil.

引用

页码：1557 / 1562

页数：6

共 50 条

[41] Synthesis Characterization and Crystal Structure of 2-(3,4,5-trimethoxyphenyl)-1-(4-fluorophenyl)-4,5-diphenyl-1H-imidazole [J].

Viveka, S. ;

Prabhuswamy, M. ;

Dinesha ;

Lokanath, N. K. ;

Nagaraja, G. K. .

MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2014, 593 (01) :261-270

[42] Design and synthesis of 4-morpholino-6-(1,2,3,6-tetrahydropyridin-4-yl)-N-(3,4,5-trimethoxyphenyl)-1,3,5-triazin-2-amine analogues as tubulin polymerization inhibitors [J].

Narva, Suresh ;

Chitti, Surendar ;

Amaroju, Suresh ;

Bhattacharjee, Debanjan ;

Rao, Bala Bhaskara ;

Jain, Nishant ;

Alvala, Mallika ;

Sekhar, Kondapalli Venkata Gowri Chandra .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (16) :3794-3801

[43] An Unexpected Product N-(3-((2-fluorobenzyl)thio)-5-methyl-4H-1,2,4-triazol-4-yl)acetimidamide: Synthesis and Structure Analysis [J].

Sun, Na-Bo ;

Liu, Xing-Hai ;

Weng, Jian-Quan ;

Tan, Cheng-Xia .

JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2013, 35 (02) :499-502

[44] Synthesis, Characterization and Crystal Structure of Samarium(III)-(E)-1-phenyl-N-(4H-1,2,4-triazol-4-yl)methanimine Complex [J].

Abu-Yamin, Abdel-Aziz .

JORDAN JOURNAL OF CHEMISTRY, 2021, 16 (02) :87-94

[45] Synthesis, Crystal Structure and Antitumor Activity of N-[5-(Benzylthio)-1,3,4-thiadiazol-2-yl]-4-chlorobenzamide [J].

马小平 ;

黄钰天 ;

宋新建 ;

王艳 ;

王军刚 ;

李耀华 .

结构化学, 2017, 36 (08) :1321-1326

[46] Synthesis,Crystal Structure and Antiproliferative Activity of Ethyl 1-(Phenylcarbamoyl)-2-3,4,5-trimethoxyphenyl)cyclopropanecarboxylae [J].

张敬一 ;

钟涵宇 ;

史国兵 .

Chinese Journal of Structural Chemistry, 2014, (06) :876-880

[47] Crystal structure of 4,5-bis(3,4,5-trimethoxyphenyl)-2H-1,2,3-triazole methanol monosolvate [J].

Madadi, Nikhil Reddy ;

Penthala, Narsimha Reddy ;

Bommagani, Shobanbabu ;

Parkin, Sean ;

Crooks, Peter A. .

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 :O1128-+

[48] Synthesis, Crystal Structure and Antifungal Activity of a New Zn(II) Complex Based on 4-(5-(Pyridin-3-yl)-4H-1,2,4-triazol-3-yl) Benzoic Acidu [J].

Song Huan ;

Wang Jia-Kai ;

Chen Xiao-Yan ;

Tian Xiao-Yan ;

Li Ying-Lian ;

Li Bing .

CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2021, 40 (01) :103-108

[49] Synthesis, Crystal Structure, Herbicidal Activity and Docking Study of 4-Cyclopropyl-3-((4-fluorobenzyl)sulfonyl)-5-methyl-4H-1,2,4-triazole [J].

Min Li-Jing ;

Qiao Li ;

Wang Han ;

Han Liang ;

Liu Xing-Hai .

CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2019, 38 (08) :1356-1361

[50] Synthesis, Crystal Structure, and Characterization of New 2,4,5-Triphenyl Imidazole: 4,5-Diphenyl-2-(3,4,5-trimethoxyphenyl)-1H-imidazole [J].

Viveka, S. ;

Prabhuswamy, M. ;

Dinesha ;

Lokanath, N. K. ;

Nagaraja, G. K. .

MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2014, 588 (01) :83-94

← 1 2 3 4 5 →