2-(benzo[d][1,3]-dioxol-5-ylmethylene)-N-ethylhydrazinecarbothioamide | 83796-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(benzo[d][1,3]-dioxol-5-ylmethylene)-N-ethylhydrazinecarbothioamide
• 英文别名: pEtTSC；EtpTSC；1-(1,3-Benzodioxol-5-ylmethylideneamino)-3-ethylthiourea
• CAS: 83796-42-3
• 化学式: C₁₁H₁₃N₃O₂S
• 分子量: 251.309
• InChiKey: ZVMPPNWGYTWTBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 2-(benzo[d][1,3]-dioxol-5-ylmethylene)-N-ethylhydrazinecarbothioamide 以 乙醇 为溶剂， 生成 [CuCl₂(2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-ethylhydrazinecarbothioamide)2]
  参考文献：
  名称：

  Anticancer activity and biophysical reactivity of copper complexes of 2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-alkylhydrazinecarbothioamides

  摘要：

  A series of copper complexes were synthesized from benzo[d][1,3]dioxole-5-carbaldehyde (piperonal) thiosemicarbazones (RHpTSC where R = H, CH3, C2H5 or C6H5 (Ph)). The complexes show interesting variations in geometry depending on the thiosemicarbazone; a dinuclear complex [Cu(HpTSC)Cl]2, a mononuclear complex [Cu(RHpTSC)2Cl2] (R = CH3 or C2H5) and another mononuclear complex [Cu(PhHpTSC)(PhpTSC)Cl] was generated. The complexes bind in a moderately strong fashion to DNA with binding constants on the order of 10(4)M(-1). They are also strong binders of human serum albumin with binding constants near 10(4) M-1. The complexes show good in vitro cytotoxic profiles against two human colon cancer cell lines (HT-116 and HT29) and two human breast cancer cell lines (MCF-7 and MDA-MB-231) with IC50 values in the low millimolar concentration range. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2011.10.032
• 作为产物：
  描述：

  胡椒醛 、 4-乙基-3-硫代氨基脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以84%的产率得到2-(benzo[d][1,3]-dioxol-5-ylmethylene)-N-ethylhydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis and characterization of mixed-ligand diimine-piperonal thiosemicarbazone complexes of ruthenium(II): Biophysical investigations and biological evaluation as anticancer and antibacterial agents

  摘要：

  We have used a novel microwave-assisted method developed in our laboratories to synthesize a series of ruthenium-thiosemicarbazone complexes. The new thiosemicarbazone ligands are derived from benzo[d][1,3]dioxole-5-carbaldehyde (piperonal) and the complexes are formulated as [(diimine)(2) Ru(TSC)](PF6)(2) (where the TSC is the bidentate thiosemicarbazone ligand). The diimine in the complexes is either 2,2'-bipyridine or 1,10-phenanthroline. The complexes have been characterized by spectroscopic means (NMR, IR and UV-Vis) as well as by elemental analysis. We have studied the biophysical characteristics of the complexes by investigating their anti-oxidant ability as well as their ability to disrupt the function of the human topoisomerase ll enzyme. The complexes are moderately strong binders of DNA with binding constants of 10(4) M-1. They are also strong binders of human serum albumin having binding constants on the order of 10(4) M-1. The complexes show good in vitro anticancer activity against human colon cancer cells, Caco-2 and HCT-116 and indeed show some cytotoxic selectivity for cancer cells. The IC50 values range from 7 to 159 mu M (after 72 h drug incubation). They also have antibacterial activity against Gram-positive strains of pathogenic bacteria with IC50 values as low as 10 mu M: little activity was seen against Gram-negative strains. It has been established that all the compounds are catalytic inhibitors of human topoisomerase II. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.02.029