1-<2,4-Dihydroxy-benzyliden>-4-phenyl-thiosemicarbazid

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-<2,4-Dihydroxy-benzyliden>-4-phenyl-thiosemicarbazid
• 英文别名: 3-[(2,4-dihydroxyphenyl)methylidene]amino-1-phenylthiourea；2,4-dihydroxybenzaldehyde 4-phenylthiosemicarbazone；1-[(2,4-dihydroxyphenyl)methylideneamino]-3-phenylthiourea
• 化学式: C₁₄H₁₃N₃O₂S
• 分子量: 287.342
• InChiKey: DQHWPCQJQSIHFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  fac-bis(acetonitrile)bromotricarbonylrhenium(I) 、 1-<2,4-Dihydroxy-benzyliden>-4-phenyl-thiosemicarbazid 以 丙酮 为溶剂， 反应 1.5h， 以62.4%的产率得到
  参考文献：
  名称：

  Preparation and characterization of rhenium(I) complexes with thiosemicarbazone ligands derived from resorcinol

  摘要：

  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.

  DOI：

  10.1016/j.poly.2013.08.038
• 作为产物：
  描述：

  4-苯基-3-硫代氨基脲 、 2,4-二羟基苯甲醛 以 乙醇 为溶剂， 反应 4.0h， 以54%的产率得到1-<2,4-Dihydroxy-benzyliden>-4-phenyl-thiosemicarbazid
  参考文献：
  名称：

  羟基取代的苯甲醛衍生的硫代半氨基甲酮，Hy和二硫代氨基甲酸酯对黄嘌呤氧化酶的抑制作用

  摘要：

  非嘌呤黄嘌呤氧化还原酶（XOR）抑制剂是嘌呤类似物别嘌呤醇的重要替代品，别嘌呤醇仍然是治疗与血液中尿酸水平升高有关的疾病的最广泛使用的药物。通过将单，二和三羟基苯甲醛与芳族硫代氨基脲，芳基酰肼和二硫代氨基甲酸酯缩合，合成了三组结构相关的席夫碱，表征并测试了其XOR抑制活性。发现苯甲醛成分对位的羟基取代具有较高的抑制活性。酰基的效力一般不如含硫羰基的席夫碱。内的缩氨基硫脲系列，氯和氰基的取代基对在相同的分析条件下测得，硫代氨基脲单元的位置进一步提高了活性，其效力比基准别嘌呤醇的效力高约四倍。为了说明席夫碱直接与酶活性位点上的钼中心结合的潜力，将每个抑制剂系列的一个代表性实例（H 2 L）与一个顺式-二氧钼（VI）单元配位。 ，以及生成的络合物[MoO 2（L）MeOH]的结构表征。然而，随后的稳态动力学研究表明，混合型抑制作用类似于已知在远离Mo中心的酶的底物进入通道内结合的抑制剂所观察到的

  DOI：

  10.1002/cmdc.201100054

文献信息

• Inhibition of Xanthine Oxidase by Thiosemicarbazones, Hydrazones and Dithiocarbazates Derived from Hydroxy-Substituted Benzaldehydes
  作者：Maria Leigh、Daniel J. Raines、Carmen E. Castillo、Anne K. Duhme-Klair

  DOI：10.1002/cmdc.201100054

  日期：2011.6.6

  and tested for XOR inhibitory activity. Hydroxy substitution in the para‐position of the benzaldehyde component was found to confer high inhibitory activities. Acyl hydrazones were generally less potent than thiocarbonyl‐containing Schiff bases. Within the thiosemicarbazone series, chloro and cyano substituents in the para‐position of the thiosemicarbazide unit increased activities further, up to potencies

  非嘌呤黄嘌呤氧化还原酶（XOR）抑制剂是嘌呤类似物别嘌呤醇的重要替代品，别嘌呤醇仍然是治疗与血液中尿酸水平升高有关的疾病的最广泛使用的药物。通过将单，二和三羟基苯甲醛与芳族硫代氨基脲，芳基酰肼和二硫代氨基甲酸酯缩合，合成了三组结构相关的席夫碱，表征并测试了其XOR抑制活性。发现苯甲醛成分对位的羟基取代具有较高的抑制活性。酰基的效力一般不如含硫羰基的席夫碱。内的缩氨基硫脲系列，氯和氰基的取代基对在相同的分析条件下测得，硫代氨基脲单元的位置进一步提高了活性，其效力比基准别嘌呤醇的效力高约四倍。为了说明席夫碱直接与酶活性位点上的钼中心结合的潜力，将每个抑制剂系列的一个代表性实例（H 2 L）与一个顺式-二氧钼（VI）单元配位。 ，以及生成的络合物[MoO 2（L）MeOH]的结构表征。然而，随后的稳态动力学研究表明，混合型抑制作用类似于已知在远离Mo中心的酶的底物进入通道内结合的抑制剂所观察到的
• Supramolecular Synthesis and Experimental and Theoretical Studies of Cocrystal Systems Based on Resorcinol-Thiosemicarbazones and N,N′-Divergent Dipyridines
  作者：Ara Núñez-Montenegro、Saray Argibay-Otero、Rosa Carballo、Ana Graña、Ezequiel M. Vázquez-López

  DOI：10.1021/acs.cgd.7b00304

  日期：2017.6.7

  methanol of a combination of several resorcinol-thiosemicarbazones (TSC) and two N,N′-divergent bipyridines (BP) led to the isolation of 14 cocrystals, some of which contained solvent in the crystal lattice. The main hydrogen bonded motifs have been identified, and some key structural factors have been analyzed by theoretical calculations. Structurally, the 14 cocrystals can be grouped into two main types

  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。
• 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.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Pb: MVol.C4, 230, page 1728 - 1732
  作者：

  DOI：——

  日期：——
• Stankoviansky, S.; Carsky, J.; Halada, S., Chemicke Zvesti, <hi>1963</hi>, vol. 17, p. 411 - 418
  作者：Stankoviansky, S.、Carsky, J.、Halada, S.

  DOI：——

  日期：——