2-[amino(pyridin-2-yl)methylidene]-N-phenylhydrazine-1-carbothioamide | 56041-32-8

• 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
• 英文名称: 2-[amino(pyridin-2-yl)methylidene]-N-phenylhydrazine-1-carbothioamide
• 英文别名: N(4)-phenyl-2-pyridineformamide thiosemicarbazone；2-pyridineformamide N(4)-phenylthiosemicarbazone；N(4)-phenyl-2-pyridinoformamide thiosemicarbazone；2-pyridinoformamide thiosemicarbazone；H2Am4DPh；1-[(Z)-[amino(pyridin-2-yl)methylidene]amino]-3-phenylthiourea
• CAS: 56041-32-8
• 化学式: C₁₃H₁₃N₅S
• 分子量: 271.346
• InChiKey: AYSZFCRARGCWCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 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：
  107
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[amino(pyridin-2-yl)methylidene]-N-phenylhydrazine-1-carbothioamide 、 四氯化锡 以 乙醇 为溶剂， 以71%的产率得到trichloro(N(4)-phenyl-2-pyridineformamide-thiosemicarbazonato)tin(IV)
  参考文献：
  名称：

  Tin(IV) complexes with 2-pyridineformamide-derived thiosemicarbazones: Antimicrobial and potential antineoplasic activities

  摘要：

  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.

  DOI：

  10.1016/j.poly.2009.01.028

文献信息

• Design and synthesis of methyl 2-{[4-phenyl-5-(pyridin-2-yl)-4<i>H</i>-1,2,4-triazol-3-yl]sulfanyl}acetate (phpy2NS) as a ligand for complexes of Group 12 elements: structural assessment and hydrogen-bonded supramolecular assembly analysis
  作者：Alfonso Castiñeiras、Isabel García-Santos、Manuel Saa

  DOI：10.1107/s205322961900682x

  日期：2019.7.1

  The reaction of 2‐cyanopyridine with N‐phenylthiosemicarbazide afforded 2‐[amino(pyridin‐2‐yl)methylidene]‐N‐phenylhydrazine‐1‐carbothioamide (Ham4ph) and crystals of 4‐phenyl‐5‐(pyridin‐2‐yl)‐2,4‐dihydro‐3H‐1,2,4‐triazole‐3‐thione (pyph3NS, 1, C13H10N4S). Crystals of methyl 2‐[4‐phenyl‐5‐(pyridin‐2‐yl)‐4H‐1,2,4‐triazol‐3‐yl]sulfanyl}acetate (phpy2NS, 2, C16H14N4O2S), derived from 1, were obtained

  2-氰基吡啶与N-苯基硫代氨基脲反应得到2- [氨基（吡啶-2-基）亚甲基] -N-苯基肼-1-碳硫酰胺（Ham4ph）和4-苯基-5-（吡啶-2-基）晶体）-2,4-二氢-3 H -1,2,4-三唑-3-硫酮（pyph3NS，1，C 13 H 10 N 4 S）。2-[[4-苯基-5-（吡啶-2-基）-甲基] -4 H -1,2,4-三唑-3-基]硫烷基}乙酸甲酯的晶体（phpy2NS，2，C 16 H 14 N 4 O 2 S），源自1可以通过Ham4ph与氯乙酸反应，然后将羧酸与甲醇进行酸催化酯化来获得。双晶（甲醇- κ ø）二（甲基2 - [4-苯基-5-（吡啶-2-基）-4- ħ 1,2,4-三唑-3-基- κ 2 Ñ 1，N 5 ]硫烷基}乙酰基]锌（II）/镉（II）六溴代己二酸酯（II），[Zn 0.76 Cd 0.24（C 16 H 14 N 4 O 2 S）2（CH
• 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。
• 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.
• Copper(II) complexes with 2-pyridineformamide-derived thiosemicarbazones: Spectral studies and toxicity against Artemia salina
  作者：Karina O. Ferraz、Solange M.S.V. Wardell、James L. Wardell、Sonia R.W. Louro、Heloisa Beraldo

  DOI：10.1016/j.saa.2009.02.020

  日期：2009.7

  The copper(II) complexes [Cu(H2Am4DH)Cl-2] (1), [Cu(H2Am4Me)Cl-2] (2), [Cu(H2Am4Et)Cl-2] (3) and [Cu(2Am4Ph)Cl] (4) with 2-pyridineformamide thiosemicarbazone (H2Am4DH) and its N(4)-methyl (H2Am4Me), N(4)-ethyl (H2Arn4Et) and N(4)-phenyl (H2Am4Ph) derivatives were studied by means of infrared and EPR spectral techniques. The crystal structure of 4 was determined. The studied compounds proved to be toxic to Artemia salina, suggesting that they could present cytotoxic activity against solid tumors. Among the free thiosemicarbazones H2Am4Ph presented higher toxicity than all other compounds, which showed comparable effects. In the case of complexes 2 and 3 toxicity is probably attributable to the complex as an entity or to a synergistic effect involving the thiosemicarbazone and copper. H2Am4Ph and complexes 2 and 3 revealed to be the most promising compounds as potential antineoplasic agents. (C) 2009 Elsevier B.V. All rights reserved.