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
收藏
页码：1557 / 1562
页数：6
相关论文
共 50 条
  • [31] Synthesis and crystal structure of 1-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
    Patil, P. S.
    Shettigar, V.
    Dharmaprakash, S. M.
    Naveen, S.
    Sridhar, M. A.
    Prasad, J. Shashidhara
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2006, 461 : 123 - 130
  • [32] Synthesis of (±)-trans-2-[3-methoxy-4-(4 chlorophenylthioethoxy)-5-(N-methyl-N-hydroxyureidyl)methylphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran
    Ram, B
    Balram, B
    Ram, SR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2003, 42 (09): : 2063 - 2068
  • [33] Crystal structure of 4-[(E)-(4-fluorobenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione
    Manjula, P. S.
    Sarojini, B. K.
    Narayana, B.
    Byrappa, K.
    Kumar, S. Madan
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O912 - U510
  • [34] Synthesis, spectral characterization, molecular docking studies, biological activity of (E)-2-((E)-3-(3,4,5-trimethoxyphenyl)allylidene) and (E)-N-phenyl 2-((E)-3-(3,4,5-trimethoxyphenyl)allylidene) hydrazinecarbothioamides and their Cu(II) complexes
    Reddy, A. Sreenath
    Mao, Jincheng
    Vanitha, S.
    Badavath, Vishnu Nayak
    Krishna, L. Sivarama
    Lavanya, M.
    Kumar, M. V. Jyothi
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2019, 23 (07) : 947 - 957
  • [35] Synthesis, Structure and Their Biological Activities of 3-[(5-H/methyl-benzoimidazol-2-yl)methylthio]-5-substituted-1,2,4-triazol-4-amine Derivatives
    An, Yue
    Zhang, Ting
    Jiang, Hua
    Zhang, Lin
    Han, Jie
    Yao, Mingxing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (07) : 1308 - 1313
  • [36] Synthesis and cytotoxicity of 3,4-disubstituted-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazoles and novel 5,6-dihydro-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives bearing 3,4,5-trimethoxyphenyl moiety (vol 22, pg 4471, 2012)
    Zhao, Pei-Liang
    Duan, An-Na
    Zou, Min
    Yang, Hai-Kui
    You, Wen-Wei
    Wu, Shu-Guang
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (17) : 3754 - 3754
  • [37] SYNTHESIS OF 5-(3,4,5-TRIMETHOXYPHENYL)-4-SUBSTITUTED ARYL-3-HYDRAZINOCARBONYLMETHYLTHIO-4H-1,2,4-TRIAZOLES AS POSSIBLE ANTI-INFLAMMATORY AGENTS
    JAISWAL, RK
    PARMAR, SS
    SINGH, SP
    BARTHWAL, JP
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (03) : 561 - 565
  • [38] Synthesis and Anticancer Activity of 3-(Substituted Aroyl)-4-(3,4,5-trimethoxyphenyl)-1H-pyrrole Derivatives
    Zhan, Xiao-Ping
    Lan, Lan
    Wang, Shuai
    Zhao, Kai
    Xin, Yu-Xuan
    Qi, Qi
    Wang, Yao-Lin
    Mao, Zhen-Min
    CHEMISTRY & BIODIVERSITY, 2017, 14 (02)
  • [39] Synthesis of (±)trans-2-[3-methoxy-4-(4-chlorophenylthioethoxy)-5-cyanophenyl]-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran
    Balram, B
    Ram, B
    Ram, SR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2003, 42 (09): : 2059 - 2062
  • [40] Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives
    Chen, Cai-Jun
    Song, Bao-An
    Yang, Song
    Xu, Guang-Fang
    Bhadury, Pinaki S.
    Jin, Lin-Hong
    Hu, De-Yu
    Li, Qian-Zhu
    Liu, Fang
    Xue, Wei
    Lu, Ping
    Chen, Zhuo
    BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (12) : 3981 - 3989
12345