salicylaldehyde N(4)-phenylthiosemicarbazone | 1185908-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: salicylaldehyde N(4)-phenylthiosemicarbazone
• 英文别名: (E)-2-(2-hydroxybenzylidene)-N-phenylhydrazine-1-carbothioamide；2-((2-Hydroxyphenyl)methylene)-N-phenylhydrazinecarbothioamide；1-[(E)-(2-hydroxyphenyl)methylideneamino]-3-phenylthiourea
• CAS: 1185908-30-8
• 化学式: C₁₄H₁₃N₃OS
• 分子量: 271.343
• InChiKey: BKJAPBJJTOJXEZ-XNTDXEJSSA-N

物化性质

• 沸点：
  429.6±47.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  88.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  salicylaldehyde N(4)-phenylthiosemicarbazone 在 氘代甲醇 作用下， 生成
  参考文献：
  名称：

  Novak, Predrag; Piculjan, Katarina; Biljan, Tomislav, Croatica Chemica Acta, 2007, vol. 80, # 3-4, p. 575 - 581

  摘要：

  DOI：
• 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 salicylaldehyde N(4)-phenylthiosemicarbazone
  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

• Modifying aroylhydrazone prochelators for hydrolytic stability and improved cytoprotection against oxidative stress
  作者：Qin Wang、Katherine J. Franz

  DOI：10.1016/j.bmc.2018.11.004

  日期：2018.12

  BSIH ((E)-N′-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)isonicotinohydrazide) is a prodrug version of the metal chelator SIH ((E)-N′-(2-hydroxybenzylidene)isonicotinohydrazide) in which a boronate group prevents metal chelation until reaction with hydrogen peroxide releases SIH, which is then available for sequestering iron(III) and inhibiting iron-catalyzed oxidative damage. While BSIH

  BSIH（（（E）-N '-（2-（4,4,5,5-tetramethyl-1,3,2-dioxaboroboro-2--2-yl）苄叉基）异烟肼）是金属螯合剂SIH（（E）-N'-（2-羟基亚苄基）异二十二酰肼）中的硼酸酯基团防止金属螯合，直到与过氧化氢反应释放出SIH，然后可用于螯合铁（III）和抑制铁催化的氧化损伤。虽然BSIH已显示出在氧化应激条件下有条件地靶向细胞螯合铁的前景，但由于BSIH以其水解产物异烟肼和2-甲酰基苯基硼酸作为平衡混合物存在于细胞培养基中的事实限制了SIH的产量。在当前的研究中，评估了几种BSIH类似物的水解稳定性，与H 2 O 2的反应结果以及螯合剂到螯合剂的转化效率。值得注意的是，对甲氧基衍生物（p-OMe）BSIH（（E）-N '-（5-甲氧基-2-（4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基）亚苄基）异烟肼基）和间位- ，第-double取代的（MD）BSIH（（ë）
• Novel thiosemicarbazone derivatives as potential antitumor agents: Synthesis, physicochemical and structural properties, DNA interactions and antiproliferative activity
  作者：Ivica Đilović、Mirta Rubčić、Višnja Vrdoljak、Sandra Kraljević Pavelić、Marijeta Kralj、Ivo Piantanida、Marina Cindrić

  DOI：10.1016/j.bmc.2008.03.006

  日期：2008.5

  The paper describes synthesis of several novel thiosemicarbazone derivatives. Furthermore, crystal and molecular structure of 4-diethylamino-salicylaldehyde 4-phenylthiosemicarbazone revealed planarity of conjugated aromatic system, which suggested the possibility of DNA binding by intercalation, especially for here studied naphthalene derivatives. However, here presented DNA binding studies excluded

  该论文描述了几种新型硫代半碳酰胺衍生物的合成。此外，4-二乙基氨基-水杨醛4-苯基硫代半脲的晶体和分子结构揭示了共轭芳族体系的平面性，这暗示了通过嵌入特别是对于本文研究的萘衍生物而言，DNA结合的可能性。但是，这里提出的DNA结合研究排除了这种作用方式。将新型衍生物的理化和结构性质与先前研究的类似物（作为参考化合物）进行比较，揭示出明显的差异。此外，新的硫代半脲衍生物（1、2和5-8）在五个肿瘤细胞系上的抗增殖活性明显高于参考化合物3和4，这支持了它们作为潜在抗肿瘤剂的进一步研究。
• Thiosemicarbazone-based selective proliferation inactivators inhibit gastric cancer cell growth, invasion, and migration
  作者：Biao Hu、Bo Wang、Bing Zhao、Qian Guo、Zhong-Hua Li、Xin-Hui Zhang、Guang-Yao Liu、Ying Liu、Ying Tang、Fan Luo、Ya Du、Ya-Xin Chen、Li-Ying Ma、Hong-Min Liu

  DOI：10.1039/c7md00353f

  日期：——

  A series of novel thiosemicarbazone derivatives were synthesized and evaluated for their antiproliferative activity against several tumor cell lines by MTT assay.

  一系列新颖的硫代半胱氨酮衍生物被合成，并通过MTT测定评估其对几种肿瘤细胞系的抗增殖活性。
• Chemistry of cyclopropenones: synthesis of new pyrrolo[2,1-b]-1,3,4-oxadiazoles
  作者：Ashraf A. Aly、Alaa A. Hassan、Mohamed A. Ameen、Alan B. Brown

  DOI：10.1016/j.tetlet.2008.04.066

  日期：2008.6

  2,3-Diphenylcyclopropenone (1) reacts with ylidene-N-phenylhydrazine-carbothioamides 2a–e to form the pyrrolo[2,1-b]-1,3,4-oxadiazoles 5a–e.

  2,3-二苯基环丙烯酮（1）与亚烷基-N-苯基肼-碳硫酰胺2a - e反应形成吡咯并[2,1- b ] -1,3,4-恶二唑5a - e。
• Metal complexes useful in metathesis and other reactions
  申请人：Walter Francis

  公开号：US20050043541A1

  公开（公告）日：2005-02-24

  This invention provides metal complexes being useful as catalyst components in metathesis reactions and in reactions involving the transfer of an atom or group to an ethylenically or acetylenically unsaturated compound or another reactive substrate and, with respect to a sub-class thereof, for the polymerisation of α-olefins and optionally conjugated dienes, with high activity at moderate tempera-tures. It also provides methods for obtaining polymers with very narrow molecular weight distribution by means of a living reaction. It also provides methods for making said metal complexes and novel intermediates involved in such methods. It further provides derivatives of said metal complexes which are suitable for covalent bonding to a carrier, the product of such covalent bonding being useful as a supported catalyst for heterogeneous catalytic reactions. It also provides a direct one-step synthesis of pyrrole, furan and thiophene compounds from diallyl compounds.

  本发明提供了金属配合物，可用作交换反应中的催化剂组分，以及涉及将原子或基团转移至乙烯基或乙炔基不饱和化合物或其他反应底物的反应中，并且针对其亚类别，用于α-烯烃和可选的共轭二烯的聚合，具有在中等温度下高活性。它还提供了通过活性反应获得非常窄的分子量分布的聚合物的方法。它还提供了制备该金属配合物和涉及这种方法的新型中间体的方法。它还提供了该金属配合物的衍生物，适用于与载体进行共价键合，该共价键合的产物可用作异相催化反应的支持催化剂。它还提供了从双烯基化合物直接合成吡咯、呋喃和噻吩化合物的一步法。