vanillin thiosemicarbazone | 5351-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: vanillin thiosemicarbazone
• 英文别名: 1-(4-hydroxy-3-methoxybenzylidene)thiosemicarbazide；4'-hydroxy-3'-methoxybenzaldehyde thiosemicarbazone；Vanillin-thiosemicarbazon；[(4-hydroxy-3-methoxyphenyl)methylideneamino]thiourea
• CAS: 5351-92-8
• 化学式: C₉H₁₁N₃O₂S
• mdl: MFCD00022158
• 分子量: 225.271
• InChiKey: FJQYXPHDGKUTQE-UHFFFAOYSA-N

物化性质

• 熔点：
  197 °C
• 沸点：
  412.2±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  vanillin thiosemicarbazone 在 hexaaquairon(III) perchlorate 作用下， 反应 2.0h， 以87%的产率得到香草醛
  参考文献：
  名称：

  Parmar, Anupama; Goyal, Rita; Kumar, Baldev, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 9, p. 941 - 942

  摘要：

  DOI：
• 作为产物：
  描述：

  香草醛 在 乙醇 、 potassium acetate 、 溶剂黄146 作用下， 生成 vanillin thiosemicarbazone
  参考文献：
  名称：

  Miyatake, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1952, vol. 72, p. 1162

  摘要：

  DOI：
• 作为试剂：
  描述：

  咪唑 、 4-碘甲苯 在 copper(II) choride dihydrate 、 vanillin thiosemicarbazone 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以73%的产率得到1-对甲苯-1H-咪唑
  参考文献：
  名称：

  用于铜 (II) 催化咪唑 N-芳基化的新型、简单且有效的氨基硫脲配体

  摘要：

  摘要 开发了一种铜催化偶联反应的新方法，涉及以CuCl2·H2O为催化剂，1-(4-羟基-3-甲氧基亚苄基)氨基硫脲(L1)为配体，咪唑与芳基卤反应。新配体L1与铜(II)的配合物首次表现出比铜(I)更好的催化效果。由于铜 (II) 的稳定性和经济性，该方法将是制备 N-芳基咪唑的一种有前途的方法。图形概要

  DOI：

  10.1080/00397911.2010.537425

文献信息

• Gold complexes with thiosemicarbazones: reactions of bi- and tridentate thiosemicarbazones with dichloro[2-(dimethylaminomethyl)phenyl-C 1,N ]gold(III), [Au(damp-C 1,N )Cl2]
  作者：Ulrich Abram、Kirstin Ortner、Ronald Gust、Klaus Sommer

  DOI：10.1039/a908712e

  日期：——

  Dichloro[2-(N,N-dimethylaminomethyl)phenyl-C1,N]gold(III), [Au(damp-C1,N)Cl2] (1), reacts with salicylaldehyde thiosemicarbazone (H2saltsc), vanilline thiosemicarbazone (Hvantsc), N-methylpyrrole aldehyde thiosemicarbazone (Hmepyrtsc), pyridoxal methylthiosemicarbazone (H2pydoxmetsc), 2-diphenylphosphinobenzaldehyde thiosemicarbazone (HPtsc) or variously substituted acetylpyridine thiosemicarbazones (HapRtsc; R = H, Me, Ph) with cleavage of the Au–N bond and protonation of the dimethylamino group. Compounds of general formulae [Au(Hdamp-C1)Cl(L)]+ (L = Hsaltsc−, vantsc−, mepyrtsc−), [Au(Hdamp-C1)Cl(L)]2+ (L = H2pydoxmetsc) or [Au(Hdamp-C1)(L)]2+ (L = Ptsc−, apRtsc−, R = H, Me, Ph) have been isolated and characterized. The presence of the σ-bonded 2-(dimethylaminomethyl)phenyl ligand is mandatory to prevent reduction of the gold(III) centre. The crystal structures of [Au(Hdamp-C1)Cl(Hsaltsc)](PF6) (3a), [Au(Hdamp-C1)Cl(mepyrtsc)]Cl (3c), [Au(Hdamp-C1)Cl(H2pydoxmetsc)]Cl2·MeOH (4), [Au(Hdamp-C1)(apPhtsc)]Cl2·2 MeOH (5c) and [Au(Hdamp-C1)(Ptsc)]Cl2· 1.5MeOH (6) have been elucidated, showing the gold atoms in distorted square-planar co-ordination environments. The potentially O,N,S-tridentate ligands H2saltsc and H2pydoxmetsc co-ordinate in a bidentate fashion and do not incorporate the OH groups in the chelating framework, whereas HapRtsc or HPtsc co-ordinate in a tridentate manner. Generally, one or more hydrogen atoms of the heterocyclic ligands and/or the NMe2H+ group form hydrogen bridges in the solid state structures. The preliminary results of antiproliferation tests on tumor cells demonstrate the considerable cytotoxicity of these new gold complexes. p

  二氯[2-(N,N-二甲氨基甲基)苯-C1,N]金(III), [Au(damp-C1,N)Cl2] (1), 与水杨醛缩氨基硫脲(H2saltsc), 香草醛缩氨基硫脲(Hvantsc), N-甲基吡咯醛缩氨基硫脲(Hmepyrtsc), 吡哆醛缩甲基氨基硫脲(H2pydoxmetsc), 2-二苯基膦基苯甲醛缩氨基硫脲(HPtsc)或者各种取代的乙酰吡啶缩氨基硫脲(HapRtsc; R = H, Me, Ph)反应, 导致Au–N键断裂并使二甲氨基质子化. 根据通式[Au(Hdamp-C1)Cl(L)]+(L = Hsaltsc−, vantsc−, mepyrtsc−), [Au(Hdamp-C1)Cl(L)]2+(L = H2pydoxmetsc), 或者[Au(Hdamp-C1)(L)]2+(L = Ptsc−, apRtsc−, R = H, Me, Ph)分离并表征得到化合物. 为了防止金(III)中心的还原, 必须存在σ键合的2-(二甲氨基甲基)苯配体. 通过测定[Au(Hdamp-C1)Cl(Hsaltsc)](PF6) (3a), [Au(Hdamp-C1)Cl(mepyrtsc)]Cl (3c), [Au(Hdamp-C1)Cl(H2pydoxmetsc)]Cl2·MeOH (4), [Au(Hdamp-C1)(apPhtsc)]Cl2·2 MeOH (5c)和[Au(Hdamp-C1)(Ptsc)]Cl2· 1.5MeOH (6)的晶体结构, 发现金原子处于扭曲的平面四边形配位环境. 潜在的O,N,S-三齿配体H2saltsc和H2pydoxmetsc以二齿的形式配位, 没有把羟基包含在螯合骨架中, 然而HapRtsc或HPtsc以三齿的形式配位. 通常, 杂环配体的一个或者多个氢原子和/或者NMe2H+形成氢键出现在固态结构中. 对肿瘤细胞的抗增殖试验的初步结果表明这些新金配合物具有较大的细胞毒性.
• Structure–activity relationship study of thiosemicarbazones on an African trypanosome: Trypanosoma brucei brucei
  作者：Houssou Raymond Fatondji、Salomé Kpoviessi、Fernand Gbaguidi、Joanne Bero、Veronique Hannaert、Joëlle Quetin-Leclercq、Jacques Poupaert、Mansourou Moudachirou、Georges Coffi Accrombessi

  DOI：10.1007/s00044-012-0208-6

  日期：2013.5

  structures. This study that was done using acetophenone thiosemicarbazone (1) as basic model, showed that: (a) the presence of lipophilic substituents in para position on benzene ring, (b) substitution of benzene ring and (c) substitution of hydrogen of thioamide function by a phenyl, strongly influence trypanocidal activity. The various modifications to basic structure (1) allowed the synthesis of 1-(4-chlorophenyl)

  探索非洲锥虫缩氨基硫脲的结构-活性关系：布氏锥虫布氏，一系列的35缩氨基硫脲（1 - 35）已被合成和表征可以通过1 H NMR，13 C NMR，和FT-IR光谱。使用“ Lilit alamar blue”方法测试所有化合物的杀锥虫活性。考虑到它们的结构，比较了硫半脲的锥虫杀菌能力。该研究结果表明，使用苯乙酮缩氨基硫脲进行（1）作为基本模型，表明：（a）中的亲脂性的取代基的存在对在苯环上的位置，（b）苯环的取代和（c）硫代酰胺官能团的氢被苯基取代，强烈影响锥虫活性。对基本结构（1）的各种修饰允许合成1-（4-氯苯基）亚乙基-4-苯基-硫代氨基脲（34）。该化合物具有3.97μM的锥虫杀灭活性，是该系列中最活跃的。
• Cytotoxicity of New 5-Phenyl-4,5-dihydro-1,3,4-thiadiazole Analogues
  作者：Mohammad Sayed Alam、Lijun Liu、Dong Ung Lee

  DOI：10.1248/cpb.59.1413

  日期：——

  A series of 5-phenyl-4,5-dihydro-1,3,4-thiadiazoles were synthesized and their cytotoxicity was examined against four human cancer cell lines, e.g. lung cancer (A549), ovarian cancer (SK-OV-3), skin cancer (SK-MEL-2), and colon cancer (HCT15). The title compounds were synthesized by condensation of thiosemicarbazide with substituted benzaldehydes, followed by cyclization with acetic anhydrides in good yields. Most of the compounds exhibited significant suppressive activity against the growth of all of the cancer cell lines. The 4-hydroxy analogue of 5-phenyl-4,5-dihydro-1,3,4-thiadiazole (2h) was most active in the inhibition of growth of the SK-MEL-2 cell line, with an IC50 value of 4.27 μg/ml; followed by compound 2a (IC50 5.16 μg/ml). The compounds 2j, 2h, and 2b, bearing 3-methoxy-4-hydroxy-, 4-hydroxy- and 4-methyl substituents in the C-5 phenyl ring respectively, exhibited the highest activity against the SK-OV-3 (IC50 7.35 μg/ml), HCT15 (IC50 8.25 μg/ml) and A549 (IC50 9.40 μg/ml) cell lines, respectively. A structure–activity relationship study revealed that an optimal electron density on the C-5 phenyl ring of 1,3,4-thiadiazoles is crucial for their cytotoxic activity against the human cancer cell lines used in the present study.

  一系列5-苯基-4,5-二氢-1,3,4-噻二唑被合成并对四种人癌细胞系（例如肺癌(A549)、卵巢癌(SK-OV-3)、皮肤癌(SK-MEL-2)和结肠癌(HCT15)）进行了细胞毒性测试。标题化合物通过硫脲与取代苯甲醛的缩合反应合成，随后用乙酸酐环化得到良好产率。大多数化合物对所有癌细胞系的生长表现出显著抑制活性。5-苯基-4,5-二氢-1,3,4-噻二唑的4-羟基类似物(2h)在抑制SK-MEL-2细胞生长方面活性最高，IC50值为4.27 μg/ml；其次是化合物2a（IC50 5.16 μg/ml）。化合物2j、2h和2b分别在C-5苯环上具有3-甲氧基-4-羟基、4-羟基和4-甲基取代基，它们对SK-OV-3（IC50 7.35 μg/ml）、HCT15（IC50 8.25 μg/ml）和A549（IC50 9.40 μg/ml）细胞系表现出最高活性。结构-活性关系研究揭示，1,3,4-噻二唑C-5苯环上的最佳电子密度对本研究中使用的人癌细胞系的细胞毒性活性至关重要。
• Synthesis of thiazole-based substituted piperidinone oximes: Profiling of antioxidant and antimicrobial activity
  作者：Salakatte Thammaiah Harini、Honnaiah Vijay Kumar、Javarappa Rangaswamy、Nagaraja Naik

  DOI：10.1134/s1068162017020042

  日期：2017.3

  The synthesis of novel thiazole-based piperidinone oximes and screening of their antioxidant and antimicrobial activity are described. The obtained results revealed that the electronic effects of active substituents at C-4 terminals of phenyl rings on either side of piperidinone skeleton, as well as at 2-hydrazinyl thiazole, played a major role in development of antioxidant and antimicrobial activity

  描述了新型噻唑基哌啶酮肟的合成及其抗氧化和抗菌活性的筛选。获得的结果表明，哌啶酮骨架两侧苯环 C-4 末端的活性取代基以及 2-肼基噻唑的电子效应在抗氧化和抗菌活性的发展中起主要作用。抗氧化活性似乎也基于噻唑环的自由基消散能力。噻唑中硫的亲核特性和哌啶酮骨架的亲脂性极大地影响了观察到的噻唑基哌啶酮肟的抗菌活性。在合成的化合物中, 2,
• Discovery of Novel Bromophenol–Thiosemicarbazone Hybrids as Potent Selective Inhibitors of Poly(ADP-ribose) Polymerase-1 (PARP-1) for Use in Cancer
  作者：Chuanlong Guo、Lijun Wang、Xiuxue Li、Shuaiyu Wang、Xuemin Yu、Kuo Xu、Yue Zhao、Jiao Luo、Xiangqian Li、Bo Jiang、Dayong Shi

  DOI：10.1021/acs.jmedchem.8b01946

  日期：2019.3.28

  Poly(ADP-ribose) polymerase-1 (PARP-1) is a new potential target for anticancer drug discovery. A series of bromophenol-thiosemicarbazone hybrids as PARP-1 inhibitors were designed, synthesized, and evaluated for their antitumor activities. Among them, the most promising compound, 11, showed excellent selective PARP-1 inhibitory activity (IC50 = 29.5 nM) over PARP-2 (IC50 > 1000 nM) and potent anticancer

  聚（ADP-核糖）聚合酶-1（PARP-1）是抗癌药物发现的新潜在目标。设计，合成并评估了一系列作为PARP-1抑制剂的溴酚-硫代半碳杂zone杂化物的抗肿瘤活性。其中，最有前途的化合物11对PARP-2（IC50> 1000 nM）表现出优异的选择性PARP-1抑制活性（IC50 = 29.5 nM），并对SK-OV-3，Bel-7402和在体内SK-OV-3细胞异种移植模型中，HepG2癌细胞系（IC50 = 2.39、5.45和4.60μM）以及肿瘤生长的抑制作用。进一步的研究表明，化合物11通过多种抗癌机制发挥了抗肿瘤作用，包括诱导凋亡和细胞周期停滞，DNA双链断裂的细胞蓄积，DNA修复改变，抑制H2O2触发的PARylation，通过产生细胞毒性活性氧而产生的抗增殖作用以及自噬。另外，化合物11显示出良好的药代动力学特性和良好的安全性。这些观察表明，化合物11可以用作发现新的抗癌药物的先导化合物。