2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone | 386254-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone
• 英文别名: Hydrazinecarbothioamide, 2-[(2,4-dihydroxyphenyl)methylene]-N-methyl-；1-[(2,4-dihydroxyphenyl)methylideneamino]-3-methylthiourea
• CAS: 386254-60-0
• 化学式: C₉H₁₁N₃O₂S
• 分子量: 225.271
• InChiKey: XKINVHZFLTXVJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-联吡啶 、 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone 以 丙酮 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  基于间苯二酚-硫代半氨基甲酮和N，N'-发散二吡啶的共晶体系的超分子合成及实验和理论研究

  摘要：

  在甲醇中的超分子合成过程是几种间苯二酚-硫代半氨基甲酮（TSC）和两个N，N'-发散性联吡啶（BP）的组合，导致分离出14个共晶体，其中一些在晶格中包含溶剂。已经确定了主要的氢键基序，并通过理论计算分析了一些关键的结构因素。从结构上讲，这14个共晶可以分为两种主要类型。第一种类型的特征是涉及溶剂的TSC / BP环状结构的形成，以及TSC组分中不存在分子内O–H··N，S（6）的相互作用。第二种类型的特征是TSC / BP无环缔合，在大多数情况下不包括溶剂，以及通常的分子内O–H···N，S（6），在TSC组件中保持交互。

  DOI：

  10.1021/acs.cgd.7b00304
• 作为产物：
  描述：

  4-甲基氨基硫脲 、 2,4-二羟基苯甲醛 以 乙醇 为溶剂， 以86%的产率得到2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone
  参考文献：
  名称：

  含有咪唑衍生物和氨基硫脲席夫碱的混合配体镍 (II) 配合物的合成、表征和生物学研究

  摘要：

  摘要 四种新的混合配体 Ni(II) 配合物 (1-4) 含有咪唑 (im) 或苯并咪唑 (bz) 和源自 2,4-二羟基苯甲醛 (24D) 和 4-甲基-3-氨基硫脲 (MT24D) 的三齿席夫碱) 或 4-苯基-3-氨基硫脲 (PT24D) 合成并使用元素和光谱分析进行表征，包括 FTIR、UV-Vis、1H NMR、13C NMR 和 Schiff 碱的质谱，同时使用 ICP-OES 对配合物进行额外分析、摩尔电导率、磁化率测量和单晶 X 射线衍射 (SXRD) 分析。磁化率表明所有金属配合物都是方形平面几何形状，而摩尔电导值表明配合物在 DMSO 中是非电解质。[Ni(MT24D)(bz)](bz)中中性复合分子的分子几何形状。CH3OH (2'), 即 2 与 1,3-苯并咪唑分子作为甲醇溶剂化物共结晶，并在 [Ni(MT24D)(im)]O2CMe.2H2O (5) 的阳离子中，1

  DOI：

  10.1016/j.molstruc.2019.126888

文献信息

• Towards a selective cytotoxic agent for prostate cancer: Interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I
  作者：Kong Wai Tan、Hoi Ling Seng、Fei Shen Lim、Shiau-Chuen Cheah、Chew Hee Ng、Kong Soo Koo、Mohd. Rais Mustafa、Seik Weng Ng、Mohd. Jamil Maah

  DOI：10.1016/j.poly.2012.03.014

  日期：2012.5

  Four thiosemicarbazones ligands, H3T(1), H3M(2), H3E(3) and H3P(4) have been prepared with good yield by refluxing 2,4-dihydroxybenzaldehyde with N(4)-substituted thiosemicarbazide in ethanol (H3T(1) = 2,4-dihydroxybenzaldehyde thiosemicarbazone: H3M(2) = 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone; H3E(3) = 2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone and H3P(4) = 2,4-dihydroxybenzaldehyde 4-phenylthiosemicarbazone). Reactions of these ligands with zinc acetates in the presence of 2,2'-bipyridine lead to the formation of zinc(II) complexes of formulation [Zn(bpy)L](5-8) (bpy = 2,2'-bipyridine; L = doubly deprotonated thiosemicarbazones = HT(5); HM(6); HE(7) and HP(8)). These compounds were characterized and their cytotoxicity and topoisomerase I inhibition activities studied. X-ray diffraction study indicates that complex 8 is five coordinated and the coordination geometry around zinc(II) is trigonal bipyramidal distorted square based pyramid (TBDSBP). The doubly deprotonated thiosemicarbazone acts as a tridentate ONS-donor ligand while 2,2-bipyridne as the NN-donor ligand. Complexes 6,7 and 8 are more cytotoxic towards PC3 (prostate cancer cell line) than RWPE-1 (prostate normal cell line). The cytotoxicity and topoisomerase I inhibition activities seem to be dependent on the N(4) substituent of the thiosemicarbazone moiety. (C) 2012 Elsevier Ltd. All rights reserved.
• Preparation and characterization of rhenium(I) complexes with thiosemicarbazone ligands derived from resorcinol
  作者：Ara Núñez-Montenegro、Rosa Carballo、Ulrich Abram、Ezequiel M. Vázquez-López

  DOI：10.1016/j.poly.2013.08.038

  日期：2013.11

  New neutral tricarbonylrhenium(I) complexes with bidentate thiosemicarbazone ligands derived from resorcinol have been prepared. Ligands were obtained by condensation reactions of 2,4-dihydroxybenzaldehyde (dhb) and 2,4-dihydroxyacetophenone (dha) with thiosemicarbazide derivatives. The metal complexes have been characterized by elemental analysis, mass spectrometry, spectroscopic methods (IR, H-1 NMR) and the crystal structures for eight of these compounds have been elucidated. The Re(I) metal centers are coordinated through the azomethine nitrogen and the sulfur atoms establishing five-membered chelate rings (kappa-S,N(3)). The deprotonation of the ligand HL6 and the labilization of the halogen produces the formation of the dimeric complex [Re-2(L-6)(2)(CO)(6)] by Re-S-Re bridges, where S is the thiolate sulfur atom from a kappa-S,N(3)-bidentate thiosemicarbazonate ligand. (C) 2013 Elsevier Ltd. All rights reserved.