N(4)-乙基-2-吡啶甲酰胺缩氨基硫脲 | 784152-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: N(4)-乙基-2-吡啶甲酰胺缩氨基硫脲
• 英文名称: 2-pyridinformamide N-4-ethylthiosemicarbazone
• 英文别名: N(4)-ethyl-2-pyridineformamide thiosemicarbazone；2-pyridineformamide N(4)-ethylthiosemicarbazone；N(4)-ethyl-2-pyridinoformamide thiosemicarbazone；2-Pyridinformamid-N(4)-ethylthiosemicarbazon；H2Am4DEt；H2Am4Et；1-[(E)-[amino(pyridin-2-yl)methylidene]amino]-3-ethylthiourea
• CAS: 784152-18-7
• 化学式: C₉H₁₃N₅S
• 分子量: 223.302
• InChiKey: YRJQZPHBSPWJTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  potassium tetrachloropalladate(II) 、 N(4)-乙基-2-吡啶甲酰胺缩氨基硫脲 以 乙醇 、 水 为溶剂， 以69.6%的产率得到[Pd(II)(2-pyridineformamide N(4)-ethylthiosemicarbazone-1H)Cl]*2H2O
  参考文献：
  名称：

  2-吡啶甲酰胺N(4)-乙基氨基硫脲过渡金属配合物的光谱和结构研究

  摘要：

  在 N(4)-乙基氨基硫脲存在下还原 2-氰基吡啶产生 2-吡啶甲酰胺 N(4)-乙基氨基硫脲，HAm4E。已经制备了钴 (III)、镍 (II)、铜 (II)、钯 (II) 和铂 (II) 的配合物，并通过摩尔电导率、磁化率和光谱技术对其进行了表征。此外，HAm4E、[Co(Am4E)2](ClO4)、[Ni(HAm4E)2](ClO4)2 和 [Ni(HAm4E)2]Cl(OAc)·AcOH·H2O 的晶体结构获得。当分别作为中性或阴离子配体配位时，通过吡啶基氮、亚胺氮和硫酮或硫醇基硫原子发生配位。HAm4E 及其金属配合物中都存在广泛的氢键，其中酰胺氢原子是重要的贡献者。

  DOI：

  10.1002/zaac.200400345
• 作为产物：
  描述：

  2-氰基吡啶 、 4-乙基-3-硫代氨基脲 在 sodium methylate 作用下， 反应 4.0h， 生成 N(4)-乙基-2-吡啶甲酰胺缩氨基硫脲
  参考文献：
  名称：

  Novel Zn(ii)-thiazolone-based solid fluorescent chemosensors: naked-eye detection for acid/base and toluene

  摘要：

  三种锌配合物具有不同配体取代基，显示出由酸/碱蒸汽或甲苯诱导的有趣荧光开关特性。

  DOI：

  10.1039/c6ra06412d

文献信息

• Ruthenium(II) complexes containing 2-pyridineformamide- and 2-benzoylpyridine-derived thiosemicarbazones and PPh3: NMR and electrochemical studies of cis–trans-isomerization
  作者：Angelica E. Graminha、Alzir A. Batista、Isolda C. Mendes、Letícia R. Teixeira、Heloisa Beraldo

  DOI：10.1016/j.saa.2007.07.005

  日期：2008.4

  disfavored by the sterical effect of two bulky groups close to each other whereas the trans isomer is disfavored by the electronic effect of competition of two phosphorous for pi-bonding d orbitals of the metal. Our results suggest that, although both factors may be operating simultaneously, in CH(2)Cl(2) solution the balance of these counterpoising effects favors the formation of the trans isomer.

  获得[RuCl（L）（PPh（3））（2）]与2-苯甲酰基吡啶和2-吡啶甲酰胺衍生的硫代半氨基甲酮（HL）的配合物，并进行了充分表征。该络合物形成顺反异构体。顺式异构体由于彼此靠近的两个大基团的空间效应而受到不利影响，而反式异构体由于两种磷对金属的π键d轨道的竞争电子效应而受到不利影响。我们的结果表明，尽管两个因素可能同时起作用，但在CH（2）Cl（2）解决方案中，这些平衡作用的平衡有利于反式异构体的形成。
• Oxorhenium(V) Complexes with Thiosemicarbazones
  作者：Isabel Garcia Santos、Ulrich Abram

  DOI：10.1002/zaac.200400004

  日期：2004.5

  [ReOCl2(L1b)], where HL1b is 2-pyridineformamide-N(4)-ethylthiosemicarbazone and the ligand occupies the equatorial coordination sphere of the complex together with one of the chloro ligands. Oxorhenium(V)—Komplexe mit Thiosemicarbazonen Neutrale Oxorhenium(V)-Komplexe mit 2-Pyridinformamidthiosemicarbazonen, HL1, entstehen bei Reaktionen von [ReOCl3(PPh3)2] mit aquivalenten Mengen der Liganden. Bei

  当 [ReOCl3 (PPh3) 2] 与等摩尔量的配体反应时，会形成与衍生自 2-吡啶甲酰胺 HL1 的缩氨基硫脲的中性氧铼 (V) 配合物。当使用过量的缩氨基硫脲并在沸腾的甲苯中长时间进行反应时，会发生金属的还原和组成为 [Re (L1) 2] + 的铼 (III) 络合物的形成。[ReOCl2 (L1b)] 的 X 射线结构证实了缩氨基硫脲去质子化并充当三齿配体，其中 HL1b 是 2-吡啶甲酰胺-N (4)-乙缩氨基硫脲，配体占据配合物的赤道配位球与氯配体之一一起。Oxorhenium (V) 与 thiosemicarbazones 的复合物 中性 oxorhenium (V) 与 2-pyridinformamide thiosemicarbazones, HL1, 产生于 [ReOCl3 (PPh3) 2] 与等量配体的反应。当在沸腾的甲苯中使用过量的配体和更长的反应时间时，金属被还原并形成组成为
• 2-Pyridinoformamide-derived thiosemicarbazones and their iron(III) complexes: Potential antineoplastic activity
  作者：Angelica E. Graminha、Felipe S. Vilhena、Alzir A. Batista、Sonia R.W. Louro、Roberta L. Ziolli、Letícia R. Teixeira、Heloisa Beraldo

  DOI：10.1016/j.poly.2007.10.008

  日期：2008.2

  The iron(III) complexes [Fe(2Am4DH)(2)]Cl (1), [Fe(2Am4Me)(2)]Cl (2) and [Fe(2Am4Et)(2)]Cl (3) with 2-pyridineformamide thiosemicarbazone (H2Am4DH) and its N(4)-methyl (H2Am4Me) and N(4)-ethyl (H2Am4Et) derivatives were obtained and characterized by means microanalyses, infrared and EPR spectra. The electrochemical behavior of the complexes was investigated. The thiosemicarbazones and complexes (1) and (2) presented toxicity against Artemia salina at low concentrations. Since this bioassay has a good correlation with cytotoxic activity in human solid tumors, the studied compounds present potential pharmacological applications. (c) 2007 Elsevier Ltd. All rights reserved.
• Vanadium complexes with 2-pyridineformamide thiosemicarbazones: In vitro studies of insulin-like activity
  作者：Isolda C. Mendes、Leida M. Botion、Adaliene V.M. Ferreira、Eduardo E. Castellano、Heloisa Beraldo

  DOI：10.1016/j.ica.2008.04.029

  日期：2009.1

  Reaction of VOCl2 with 2-pyridineformamide thiosemicarbazone (H2Am4DH) and its N(4)-methyl (H2Am4Me), N(4)-ethyl (H2Am4Et) and N(4)-phenyl (H2Am4Ph) derivatives in ethanol gave as products [VO(H2Am4DH) Cl-2] (1), [VO(H2Am4Me) Cl-2] center dot 1/2HCl (2), [VO(H2Am4Et) Cl-2] center dot HCl (3) and [VO(2Am4Ph) Cl] (4). Upon the dissolution of 1-4 in water, oxidation immediately occurs with the formation of [VO2(2Am4DH)] (5), [VO2(2Am4Me)] (6), [VO2(2Am4Et)] (7) and [VO2(2Am4Ph)] (8). The crystal and molecular structures of 5 and 6 were determined. Complexes 5-8 inhibited glycerol release in a similar way to that observed with insulin but showed a low enhancing effect on glucose uptake by rat adipocytes. (C) 2008 Elsevier B.V. All rights reserved.
• Tin(IV) complexes with 2-pyridineformamide-derived thiosemicarbazones: Antimicrobial and potential antineoplasic activities
  作者：Isolda C. Mendes、Fernanda B. Costa、Geraldo M. de Lima、José D. Ardisson、Isabel Garcia-Santos、Alfonso Castiñeiras、Heloisa Beraldo

  DOI：10.1016/j.poly.2009.01.028

  日期：2009.4

  Reaction of tin tetrachloride with 2-pyridineformamide thiosemicarbazone (H2Am4DH) and its N(4)-methyl (H2Am4Me), N(4)-ethyl (H2Am4Et) and N(4)-phenyl (H2An-t4Ph) derivatives gave [Sn(2Am4DH)Cl-3] (1), [Sn(2Am4Me)Cl-3] (2), [Sn(2Am4Et)Cl-3] (3) and [Sn(2Am4Ph)Cl-3] (4) as products, in which an anionic thiosemicarbazone coordinates to the metal centre along with three chloride ions. The crystal structures of 1 and 2 were determined. The thiosemicarbazones were moderately active against Candida albicans and Pseudomonas aeruginosa. Upon coordination to tin(IV) the antimicrobial activity of the thiosemicarbazones increases. The studied compounds proved to be toxic to Artemia salina, suggesting that they could present cytotoxic activity against solid tumors. (C) 2009 Elsevier Ltd. All rights resolved.