N-ethyl-2-(3,5-dichloro-2-hydroxybenzylidene)hydrazinecarbothioamide | 283155-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-ethyl-2-(3,5-dichloro-2-hydroxybenzylidene)hydrazinecarbothioamide
• 英文别名: 3,5-dichloro-2-hydroxybenzaldehyde-N(4)-ethylthiosemicarbazone；3,5-chlorosalicylaldehyde 2-ethylthiosrmicarbazone；3,5-dichlorosalicylaldehyde 4-ethylthiosemicarbazone；1-[(3,5-Dichloro-2-hydroxyphenyl)methylideneamino]-3-ethylthiourea
• CAS: 283155-54-4
• 化学式: C₁₀H₁₁Cl₂N₃OS
• 分子量: 292.189
• InChiKey: LPOUICRMYKUGGG-UHFFFAOYSA-N

物化性质

• 沸点：
  402.9±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  88.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-ethyl-2-(3,5-dichloro-2-hydroxybenzylidene)hydrazinecarbothioamide 、 二丁基二氯化锡 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以78%的产率得到[Bu₂Sn(cdet)]
  参考文献：
  名称：

  Diorganotin(IV) complexes of 3,5-dichloro-2-hydroxybenzaldehyde-N(4)-ethylthiosemicarbazone: Synthesis, spectral characterization and crystal structure

  摘要：

  Three new diorganotin(IV) complexes of the formulae [Me2Sn(cdet)] (2), [Bu2Sn(cdet)] (3) and [Ph2Sn(cdet)] (4) have been synthesized by the reaction of 3,5-dichloro-2-hydroxybenzaldehyde-N(4)-ethylthiosemicarbazone [H(2)cdet, (1)] and appropriate diorganotin(IV) chloride in the presence of KOH in absolute methanol. These compounds have been characterized by CHN analyses, UV-Vis, FT-IR, H-1, C-13 and Sn-119 NMR spectroscopic techniques. The molecular structures of the ligand (1) and its diphenyltin(IV) complex (4) have been determined by X-ray diffraction analysis. The ligand H(2)cdet (1) remains as the thione form in the solid state. The crystal structure of [Ph2Sn(cdet)] (4) revealed that the ligand is coordinated to central tin(IV) atom as a dinegatively tridentate chelating agent via the phenoxide oxygen atom, the azomethine nitrogen atom and the thiolate sulfur atom. The Sn-119 NMR chemical shift for the complexes (2-4) are found to be -177.08 to -169.22 ppm, confirming five coordinated tin(IV) centre. X-ray crystal structure showed that the coordination geometry of central tin(IV) atom is distorted trigonal bipyramid. The oxygen and sulfur atoms are in axial positions while two phenyl groups and the azomethine nitrogen atom of the ligand occupy the equatorial positions. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.06.015
• 作为产物：
  描述：

  4-乙基-3-硫代氨基脲 、 3,5-二氯水杨醛 以 乙醇 为溶剂， 反应 2.0h， 以79%的产率得到N-ethyl-2-(3,5-dichloro-2-hydroxybenzylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  新型缩硫脲衍生物的合成、晶体结构和体外抗癌研究

  摘要：

  图形摘要摘要缩硫脲是一类重要的具有显着生物学特性的化合物。这些化合物用作合成具有生物学价值的配位化合物的稳定配体。当前的研究描述了四种新的 N(3)-乙基缩氨基硫脲衍生物的合成及其体外抗癌测试。本研究的目的是观察芳香环上的各种取代基对癌细胞生长的影响。合成的化合物通过NMR（1H和13C）光谱表征，并且使用单晶X射线晶体学技术确定每种化合物的分子结构。有趣的是，化合物 4 似乎有两个晶体学不同的单元（A 和 B），彼此之间的键长和角度略有不同。测试了所有化合物对人结肠癌 (HCT 116) 和乳腺癌 (MCF-7) 细胞系的体外抗癌特性。与具有乙氧基和烯丙基取代的化合物（3 和 4）相比，具有卤化物（Cl 和 Br）取代的化合物（1 和 2）显示出显着的活性，表明卤化物可能参与对抗癌细胞。

  DOI：

  10.1080/10426507.2014.995299

文献信息

• Dinuclear and polynuclear dioxomolybdenum(VI) Schiff base complexes: Synthesis, structural elucidation, spectroscopic characterization, electrochemistry and catalytic property
  作者：Ngui Khiong Ngan、Kong Mun Lo、Chee Seng Richard Wong

  DOI：10.1016/j.poly.2011.11.057

  日期：2012.2

  dioxomolybdenum(VI) [(MoO2)L′(D-D)]n complexes were achieved by the reaction of the second type of dinuclear dioxomolybdenum(VI) complex, [(MoO2)2L′D2], with the bidentate ligand 4,4′-bipyridine (D-D). These complexes were characterized by elemental analysis, electronic spectra, IR, 1H and 13C NMR spectroscopies, thermogravimetric analysis and cyclic voltammetry. An X-ray study shows that each molybdenum site

  已经合成了几种新的双核和多核二氧钼（VI）Schiff碱配合物。双（乙酰丙酮）二氧合钼的与5-dichlorosalicylaldehyde 4- ethylthiosemicarbazide（反应L1 / L2在4,4'-联吡啶（4,4'-联吡啶）或4,4'-联吡啶的存在下）Ñ，Ñ ' -二氧化碳（4,4'-dpdo）生成双核顺-二氧钼钼配合物[（MoO 2）2 L 2（DD）]，其中双齿配体4,4'-联吡啶或4,4'-联吡啶N，N'-二氧化物（DD），在两个钼原子之间形成了一座桥梁。第二种双核二氧钼钼（VI）席夫碱配合物[（MoO 2）2 L'D 2 ]是通过双（乙酰丙酮基）二氧钼钼与1,4-双（3-乙氧基-水杨醛甲醛碳酰肼基）反应形成的乙醇或六甲基磷酰胺（D）存在下的丁烷（L ' ）。在这种情况下，两个钼原子不直接由二齿配体桥接，而是在两端均与对称六齿席夫碱配体的O，N，O供体原子配位。多核二氧钼（VI）[（MoO
• Diorganotin(IV) complexes of 3,5-dichloro-2-hydroxybenzaldehyde-N(4)-ethylthiosemicarbazone: Synthesis, spectral characterization and crystal structure
  作者：M.A. Salam、Rosenani A. Haque

  DOI：10.1016/j.ica.2015.06.015

  日期：2015.8

  Three new diorganotin(IV) complexes of the formulae [Me2Sn(cdet)] (2), [Bu2Sn(cdet)] (3) and [Ph2Sn(cdet)] (4) have been synthesized by the reaction of 3,5-dichloro-2-hydroxybenzaldehyde-N(4)-ethylthiosemicarbazone [H(2)cdet, (1)] and appropriate diorganotin(IV) chloride in the presence of KOH in absolute methanol. These compounds have been characterized by CHN analyses, UV-Vis, FT-IR, H-1, C-13 and Sn-119 NMR spectroscopic techniques. The molecular structures of the ligand (1) and its diphenyltin(IV) complex (4) have been determined by X-ray diffraction analysis. The ligand H(2)cdet (1) remains as the thione form in the solid state. The crystal structure of [Ph2Sn(cdet)] (4) revealed that the ligand is coordinated to central tin(IV) atom as a dinegatively tridentate chelating agent via the phenoxide oxygen atom, the azomethine nitrogen atom and the thiolate sulfur atom. The Sn-119 NMR chemical shift for the complexes (2-4) are found to be -177.08 to -169.22 ppm, confirming five coordinated tin(IV) centre. X-ray crystal structure showed that the coordination geometry of central tin(IV) atom is distorted trigonal bipyramid. The oxygen and sulfur atoms are in axial positions while two phenyl groups and the azomethine nitrogen atom of the ligand occupy the equatorial positions. (C) 2015 Elsevier B.V. All rights reserved.
• Asynthesis, Crystal Structures and in Vitro Anticancer Studies of New Thiosemicarbazone Derivatives
  作者：Mouayed A. Hussein、Muhammad Adnan Iqbal、Muhammad Asif、Rosenani A. Haque、Mohammed B. Khadeer Ahamed、Amin M. S. Abdul Majid、Teoh Siang Guan

  DOI：10.1080/10426507.2014.995299

  日期：2015.9.2

  ABSTRACT Abstract Thiosemicarbazones are an important class of compounds having significant biological properties. These compounds are used as stable ligands for the synthesis of coordination compounds of biological worth. The current study describes syntheses of four new N(3)-ethyl thiosemicarbazone derivatives and their in vitro anticancer testing. The purpose of the study was to observe the effect of various

  图形摘要摘要缩硫脲是一类重要的具有显着生物学特性的化合物。这些化合物用作合成具有生物学价值的配位化合物的稳定配体。当前的研究描述了四种新的 N(3)-乙基缩氨基硫脲衍生物的合成及其体外抗癌测试。本研究的目的是观察芳香环上的各种取代基对癌细胞生长的影响。合成的化合物通过NMR（1H和13C）光谱表征，并且使用单晶X射线晶体学技术确定每种化合物的分子结构。有趣的是，化合物 4 似乎有两个晶体学不同的单元（A 和 B），彼此之间的键长和角度略有不同。测试了所有化合物对人结肠癌 (HCT 116) 和乳腺癌 (MCF-7) 细胞系的体外抗癌特性。与具有乙氧基和烯丙基取代的化合物（3 和 4）相比，具有卤化物（Cl 和 Br）取代的化合物（1 和 2）显示出显着的活性，表明卤化物可能参与对抗癌细胞。