2-(1-(pyridin-2-yl)ethylidene)-N-(4'-tolyl)hydrazinecarbothioamide | 70618-23-4

• 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: 2-(1-(pyridin-2-yl)ethylidene)-N-(4'-tolyl)hydrazinecarbothioamide
• 英文别名: methyl 2-pyridyl ketone 4-(4-tolyl)thiosemicarbazone；N(4)-para-tolyl 2-acetylpyridine thiosemicarbazone；N(4)-para-tolyl-2-acetylpyridine thiosemicarbazone；2-acetylpyridine N(4)-para-tolylthiosemicarbazone；H2Ac4pT；1-(4-methylphenyl)-3-(1-pyridin-2-ylethylideneamino)thiourea
• CAS: 70618-23-4
• 化学式: C₁₅H₁₆N₄S
• 分子量: 284.385
• InChiKey: ZKSCCNZKLCCYNG-UHFFFAOYSA-N

物化性质

• 沸点：
  430.3±47.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  gallium(III) nitrate 、 2-(1-(pyridin-2-yl)ethylidene)-N-(4'-tolyl)hydrazinecarbothioamide 以 乙醇 为溶剂， 反应 7.0h， 以58%的产率得到bis[N(4)-para-tolyl-2-acetylpyridinethiosemicarbazonato]gallium(III) nitrate
  参考文献：
  名称：

  镓（III）与2-乙酰基吡啶衍生的硫代半氨基甲酮类化合物的复合物：抗菌和细胞毒性作用以及与微管蛋白相互作用的研究。

  摘要：

  配合物[Ga（2Ac4pFPh）（2）] NO（3）（1），[Ga（2Ac4pClPhPh（2）] NO（3）（2），[Ga（2Ac4pIPhh（2）] NO（3）（3 ），用2-获得[Ga（2Ac4pNO（2）Ph）（2）] NO（3）·3H（2）O（4）和[Ga（2Ac4pT）（2）] NO（3）（5）乙酰基吡啶N（4）-对氟苯基-（H2Ac4pFPh），2-乙酰基吡啶N（4）-对氯苯基-（H2Ac4pClPh），2-乙酰基吡啶N（4）-对碘苯基-（H2Ac4pIPh），2-乙酰基吡啶N （4）-对硝基苯基-（H2Ac4pNO（2）Ph）和2-乙酰基吡啶N（4）-对甲苯基-（H2Ac4pT）硫代半脲。1-5显示了抗微生物和细胞毒性特性。与镓（III）的配位被证明是改善铜绿假单胞菌和白色念珠菌活性的有效策略。该复合物对纳摩尔浓度的恶性胶质母细胞瘤和乳腺癌细胞具有高度的细胞毒性。该化合物在

  DOI：

  10.1007/s10534-012-9603-1
• 作为产物：
  描述：

  对甲苯异硫氰酸酯 在 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 2-(1-(pyridin-2-yl)ethylidene)-N-(4'-tolyl)hydrazinecarbothioamide
  参考文献：
  名称：

  Pape, Veronika F.S.; Tóth, Szilárd; Füredi, András, European Journal of Medicinal Chemistry, 2016, vol. 117, p. 335 - 354

  摘要：

  DOI：

文献信息

• Chemistry of ruthenium(II) complexes of the tridentate NNS donor methyl 2-pyridyl ketone 4-(4-tolyl)thiosemicarbazone. Isolation and structural characterisation of a novel ruthenium(II) complex containing a co-ordinated imine of an α-N heterocyclic ketone
  作者：Milan Maji、Madhumita Chatterjee、Saktiprosad Ghosh、Shyamal Kumar Chattopadhyay、Bo-Mu Wu、Thomas C. W. Mak

  DOI：10.1039/a806341i

  日期：——

  A series of ruthenium(II) complexes of the NNS donor ligand methyl 2-pyridyl ketone 4-(4-tolyl)thiosemicarbazone (HL) has been synthesized using RuCl3·xH2O and [Ru(PPh3)3Cl2]: [Ru(HL)2][ClO4]2 1, [Ru(L)(PPh3)2Cl] 2, [Ru(HL)(PPh3)2Cl]Cl 3, [Ru(HL)(PPh3)2Cl]PF6 4, [Ru(L)(PPh3)(bpy)]PF6 5, [Ru(L)(PPh3)(dppe)]PF6 6, [Ru(HL)(PPh3)(pic)]PF6 7 and [Ru(HL)(PPh3)(mpi)]Cl2 8 [where bpy = 2,2′-bipyridine, dppe = 1,2-bis(diphenylphosphino)ethane, Hpic = pyridine-2-carboxylic acid, mpi = methyl(2-pyridyl)methyleneimine]. Chemical and electrochemical studies have been carried out. Structures of the compounds 3·CH2Cl2 3 and 8·CH2Cl2·3H2O have been determined by single crystal X-ray diffraction. The thione form of the ligand (HL) is chelated to the ruthenium centre through the pyridine nitrogen, imine nitrogen and the thione sulfur atom. The existence of a new unstable ligand methyl(2-pyridyl)methyleneimine (mpi) co-ordinated to RuII through the pyridine and imine nitrogen atoms was confirmed from the crystal structure of compound 8.

  利用 RuCl3Â-xH2O 和 [Ru(PPh3)3Cl2]，合成了一系列 NNS 供体配体甲基 2-吡啶基酮 4-(4-甲苯基)硫代氨基甲酸(HL)的钌(II)配合物：[Ru(HL)2][ClO4]2 1、[Ru(L)(PPh3)2Cl] 2、[Ru(HL)(PPh3)2Cl]Cl 3、[Ru(HL)(PPh3)2Cl]PF6 4、[Ru(L)(PPh3)(py)]PF6 5、[Ru(L)(PPh3)(dppe)]PF6 6、[Ru(HL)(PPh3)(pic)]PF6 7 和 [Ru(HL)(PPh3)(mpi)]Cl2 8 [其中 bpy = 2、2â²-联吡啶，dppe = 1,2-双（二苯基膦）乙烷，Hpic = 吡啶-2-羧酸，mpi = 甲基（2-吡啶基）亚甲基亚胺]。已进行了化学和电化学研究。化合物 3Â-CH2Cl2 3 和 8Â-CH2Cl2Â-3H2O 的结构已通过单晶 X 射线衍射确定。配体（HL）的硫酮形式通过吡啶氮、亚胺氮和硫酮硫原子与钌中心螯合。化合物 8 的晶体结构证实了一种新的不稳定配体甲基（2-吡啶基）亚甲基亚胺（mpi）通过吡啶和亚胺氮原子与 RuII 配位。
• Coordination to copper(II) strongly enhances the in vitro antimicrobial activity of pyridine-derived N(4)-tolyl thiosemicarbazones
  作者：Isolda C. Mendes、Juliana P. Moreira、Antonio S. Mangrich、Solange P. Balena、Bernardo L. Rodrigues、Heloisa Beraldo

  DOI：10.1016/j.poly.2007.03.002

  日期：2007.8

  Five copper(II) complexes with N(4)-ortho, N(4)-meta and N(4)-para-tolyl thiosemicarbazones derived from 2-formyl and 2-acetylpyridine were obtained and thoroughly characterized. The crystal structure of N(4)-meta-tolyl-2-acetylpyridine thiosemicarbazone (H2Ac4mT) was determined, as well as that of its copper(II) complex [Cu(2Ac4mT)Cl], which contains an anionic ligand and a chloride in the coordination sphere of the metal. The in vitro antimicrobial activities of all thiosemicarbazones and their copper(II) complexes were tested against Salmonella typhinturium and Candida albicans. Upon coordination a substantial decrease in the minimum inhibitory concentration, from 225 to 1478 mu mol L-1 for the thiosernicarbazones to 5-30 mu mol L-1 for the complexes was observe against the growth of Salmonella typhimurium and from 0.7-26 to 0.3-7 mu mol L-1 against the growth of C albicans, suggesting that complexation to copper(II) could be an interesting strategy of dose reduction. (c) 2007 Elsevier Ltd. All rights reserved.
• Ruthenium(II) complexes containing N(4)-tolyl-2-acetylpyridine thiosemicarbazones and phosphine ligands: NMR and electrochemical studies of cis–trans isomerization
  作者：Angelica E. Graminha、Alzir A. Batista、Javier Ellena、Eduardo E. Castellano、Letícia R. Teixeira、Isolda C. Mendes、Heloisa Beraldo

  DOI：10.1016/j.molstruc.2007.04.032

  日期：2008.3

  [Ru(HL)(PPh3)(2)Cl]Cl complexes have been obtained in which HL = N(4)-ortho (complex 1), N(4)-meta (complex 2) and N(4) pctratolyl 2-acetylpyridine thiosemicarbazone (complex 3). NMR and electrochemical studies indicate that both cis and trans isomers exist in solution, and that the cis isomers are converted into the trans isomers with time. Crystal structure determination of (1) reveals that the traps isomer is formed in the solid state. (c) 2007 Elsevier B.V. All rights reserved.
• US8273701B2
  申请人：——

  公开号：US8273701B2

  公开（公告）日：2012-09-25
• [EN] METHOD FOR DIAGNOSING NON-SMALL CELL LUNG CARCINOMA<br/>[FR] METHODE DE DIAGNOSTIC DE CARCINOME PULMONAIRE NON A PETITES CELLULES
  申请人：DARTMOUTH COLLEGE

  公开号：WO2007027421A2

  公开（公告）日：2007-03-08

  [EN] The present invention relates to the constitutive activity of the Hedgehog pathway in non-small cell lung carcinoma (NSCLC) . A method for diagnosing NSCLC by detecting the level of a component of the Hedgehog pathway is provided, as is a method for identifying subjects that will respond positively to treatment with a Hedgehog pathway antagonist. Methods for treating subjects with cancer or cancers resistant to Hedgehog pathway antagonists are also provided.
  [FR] Cette invention concerne l'activité constitutive de la voie Hedgehog dans un carcinome pulmonaire non à petites cellules (NSCLC). Cette invention concerne également une méthode de diagnostic d'un carcinome pulmonaire non à petites cellules (NSCLC) consistant à détecter le niveau d'un composant de la voie Hedgehog, ainsi qu'une méthode d'identification de sujets réagissant positivement à un traitement faisant appel à un antagoniste de la voie Hedgehog. Cette invention concerne en outre des méthodes de traitement de sujets atteints d'un ou plusieurs cancers résistant aux antagonistes de la voie Hedgehog.