(E)-4-phenyl-1-(pyridin-3-ylmethylene)-thiosemicarbazide | 67526-46-9

• 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: (E)-4-phenyl-1-(pyridin-3-ylmethylene)-thiosemicarbazide
• 英文别名: (E)-N-phenyl-2-(pyridin-3-ylmethylene)hydrazine-1-carbothioamide；3-formylpyridine 4-phenylthiosemicarbazone；pyridine-3-carbaldehyde-(4-phenyl thiosemicarbazone)；Pyridin-3-carbaldehyd-(4-phenyl-thiosemicarbazon)；nicotinaldehyde N-phenylthiosemicarbazone；1-phenyl-3-[(E)-pyridin-3-ylmethylideneamino]thiourea
• CAS: 67526-46-9
• 化学式: C₁₃H₁₂N₄S
• 分子量: 256.331
• InChiKey: XIKULJQYALWOGW-XNTDXEJSSA-N

物化性质

• 熔点：
  219-220 °C
• 沸点：
  412.5±37.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 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：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-phenyl-1-(pyridin-3-ylmethylene)-thiosemicarbazide 在 iron(III) chloride hexahydrate 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以25%的产率得到N-phenyl-5-(pyridin-3-yl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  PESTICIDAL COMPOSITIONS

  摘要：

  根据公式一的分子的使用在本文件中披露。

  公开号：

  US20120053146A1
• 作为产物：
  描述：

  硫代异氰酸苯酯 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (E)-4-phenyl-1-(pyridin-3-ylmethylene)-thiosemicarbazide
  参考文献：
  名称：

  Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents

  摘要：

  In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 mu M, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial-mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112349

文献信息

• Crystal structures of 3/4-pyridyl-based thiosemicarbazones and related Cu and Ni coordination compounds
  作者：Tarlok Singh Lobana、Mani Kaushal、Robin Bhatia、Ritu Bala、Ray J. Butcher、Jerry P. Jasinksi

  DOI：10.1107/s205322962101319x

  日期：2022.1.1

  bis(3-formylpyridine 4-ethylthiosemicarbazonato-κ2N1,S)nickel(II), [Ni(C9H11N4S)2], 4, are reported. In complex 3, the thio-ligand coordinates in a neutral form to the Cu atom through its S-donor atom, and in complex 4, the anionic thio-ligand chelates to the Ni atom through N- and S-donor atoms. The geometry of complex 3 is distorted tetrahedral [bond angles 99.70 (5)–123.23 (5)°], with the P—Cu—P bond angle being

  在这项研究中，硫配体 3-甲酰基吡啶 4-苯基氨基硫代氨基脲 (C 13 H 12 N 4 S, 1 ) 和 4-苯甲酰基吡啶 4-乙基氨基氨基硫脲 (C 15 H 16 N 4 S, 2 ) 的晶体结构和两种新的配位化合物，氯代(3-甲酰基吡啶4-苯基硫代氨基脲-κS )双(三苯基膦-κP )铜(I)乙腈单溶剂化物，[CuCl(C 13 H 12 N 4 S)(C 18 H 15 P) 2 ]·CH 3 CN, 3, 和双(3-甲酰基吡啶4-乙基硫代氨基脲-κ 2 N 1 , S ) 镍(II), [Ni(C 9 H 11 N 4 S) 2 ], 4的报道。在配合物3中，硫配体通过其 S 供体原子以中性形式与 Cu 原子配位，而在配合物4中，阴离子硫配体通过 N 和 S 供体原子与 Ni 原子螯合。配合物3的几何形状是扭曲的四面体 [键角 99.70 (5)–123.23 (5)°]，其中
• Pesticidal compositions
  申请人：Parker Marshall H.

  公开号：US08604211B2

  公开（公告）日：2013-12-10

  Molecules according to Formula One: and their uses are disclosed herein.

  根据化学式一，揭示了分子及其用途。
• Grammaticakis, Bulletin de la Societe Chimique de France, 1956, p. 109,115
  作者：Grammaticakis

  DOI：——

  日期：——
• Vio; Mamolo; Laneve, Il Farmaco, 1989, vol. 44, # 2, p. 165 - 172
  作者：Vio、Mamolo、Laneve

  DOI：——

  日期：——
• VIO, L.;MAMOLO, M. G.;LANEVE, A., FARMACO, 44,(1989) N, C. 165-184
  作者：VIO, L.、MAMOLO, M. G.、LANEVE, A.

  DOI：——

  日期：——