(Z)-N'-(1-pyridin-2-ylethylidene)hydrazinecarbodithioic acid methyl ester | 26151-76-8

• 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: (Z)-N'-(1-pyridin-2-ylethylidene)hydrazinecarbodithioic acid methyl ester
• 英文别名: methyl 2-(1-(pyridin-2-yl)ethylidene)hydrazine-1-carbodithioate；methyl (Z)-2-(1-(pyridin-2-yl)ethylidene)hydrazine-1-carbodithioate；methyl N-[(E)-1-pyridin-2-ylethylideneamino]carbamodithioate；methyl N-[(Z)-1-pyridin-2-ylethylideneamino]carbamodithioate
• CAS: 26151-76-8
• 化学式: C₉H₁₁N₃S₂
• 分子量: 225.338
• InChiKey: IFRMECQLFGLWCS-XFFZJAGNSA-N

物化性质

• 沸点：
  355.5±34.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 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：
  94.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-己基乙二胺 、 (Z)-N'-(1-pyridin-2-ylethylidene)hydrazinecarbodithioic acid methyl ester 以 N,N-二甲基甲酰胺 为溶剂， 以24.7%的产率得到(Z)-2-(1-(2-pyridyl)ethylene)-N-(2-(hexylamino)ethyl)hydrazinothioamide
  参考文献：
  名称：

  取代缩胺硫脲类化合物及其在抗结核杆菌中的应用

  摘要：

  本发明属于药物化学领域，涉及下式(I)缩胺硫脲类化合物，其几何异构体及其药物上可接受的盐和/或其溶剂化物和/或其水合物，及含有此化合物的药物组合物，用于治疗结核杆菌方面的用途。

  公开号：

  CN111362868A
• 作为产物：
  描述：

  2-乙酰基吡啶 、 肼基二硫代甲酸甲酯 以 异丙醇 为溶剂， 生成 (Z)-N'-(1-pyridin-2-ylethylidene)hydrazinecarbodithioic acid methyl ester
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Parasiticidal Thiosemicarbazone Cysteine Protease Inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi

  摘要：

  We have synthesized a library of thiosemicarbazones and screened them against three parasitic cysteine proteases, cruzain, falcipain-2, and rhodesain, and against the respective parasite sources of these three proteases, Trypanosoma cruzi, Plasmodium falciparum, and Trypanosoma brucei. The screens identified compounds that were effective against the enzymes and the parasites but also some compounds that were parasiticidal despite a lack of activity against the proteases. Several compounds were effective in killing all tested parasites. These promising lead compounds were tested for general toxicity in mice, and only one produced observable toxicity after 62 h. Our results suggest that thiosemicarbazones represent validated drug leads that kill several species of protozoan parasites through the inhibition of cysteine proteases as well as other novel targets.

  DOI：

  10.1021/jm030549j

文献信息

• [EN] ANTI-PARASITIC COMPOUNDS AND METHODS OF THEIR USE<br/>[FR] COMPOSES ANTIPARASITAIRES ET LEURS PROCEDES D'UTILISATION
  申请人：UNIV CALIFORNIA

  公开号：WO2005087211A1

  公开（公告）日：2005-09-22

  The present invention provides a novel class of compounds that disrupt the parasitic infectious life cycle and serve as promising agents for anti-parasitic therapy.

  本发明提供了一类新型化合物，可以破坏寄生虫的传染生命周期，并作为抗寄生虫疗法的有希望的药物。
• Copper-Binding Small Molecule Induces Oxidative Stress and Cell-Cycle Arrest in Glioblastoma-Patient-Derived Cells
  作者：Kenichi Shimada、Eduard Reznik、Michael E. Stokes、Lakshmi Krishnamoorthy、Pieter H. Bos、Yuyu Song、Christine E. Quartararo、Nen C. Pagano、Darren R. Carpizo、Ana C. deCarvalho、Donald C. Lo、Brent R. Stockwell

  DOI：10.1016/j.chembiol.2018.02.010

  日期：2018.5

  Transition metals are essential, but deregulation of their metabolism causes toxicity. Here, we report that the compound NSC319726 binds copper to induce oxidative stress and arrest glioblastoma-patient-derived cells at picomolar concentrations. Pharmacogenomic analysis suggested that NSC319726 and 65 other structural analogs exhibit lethality through metal binding. Although NSC319726 has been reported to function as a zinc ionophore, we report here that this compound binds to copper to arrest cell growth. We generated and validated pharmacogenomic predictions: copper toxicity was substantially inhibited by hypoxia, through an hypoxia-inducible-factor-1 alpha-dependent pathway; copper-bound NSC319726 induced the generation of reactive oxygen species and depletion of deoxyribosyl purines, resulting in cell-cycle arrest. These results suggest that metal-induced DNA damage may be a consequence of exposure to some xenobiotics, therapeutic agents, as well as other causes of copper dysregulation, and reveal a potent mechanism for targeting glioblastomas.
• ANTI-PARASITIC COMPOUNDS AND METHODS OF THEIR USE
  申请人：The Regents of the University of California

  公开号：EP1734939A1

  公开（公告）日：2006-12-27
• [EN] TARGETED DELIVERY OF 1, 2, 4, 5-TETRAOXANE COMPOUNDS AND THEIR USES<br/>[FR] ADMINISTRATION CIBLÉE DE COMPOSÉS DE 1,2,4,5-TÉTRAOXANE ET LEURS UTILISATIONS
  申请人：[en]YANG, Dan

  公开号：WO2022161490A1

  公开（公告）日：2022-08-04

  1, 2, 4, 5-tetraoxane compounds and derivatives thereof that have anticancer properties are disclosed. Pharmaceutical compositions and pharmaceutical formulations in unit dosage form suitable for the delivery of the compounds to a subject in need thereof are disclosed. The pharmaceutical compositions or formulations may include one or more active agents in addition to the compounds, such as one or more additional anticancer agents. Methods for treating a cancer, reducing a cancer, or treating or ameliorating one or more symptoms associated with a cancer in a subject are also disclosed. The methods include (i) administering to a subject in need thereof an effective amount of the compound (s). The compound (s) can be administered by oral administration, parenteral administration, inhalation, mucosal administration, or a combination thereof. The compound can selectively kill cancer cells and/or cancer stem cells over non-cancerous cells by triggering ferroptosis in the cancer cells and/or cancer stem cells.
• Synthesis and Structure−Activity Relationships of Parasiticidal Thiosemicarbazone Cysteine Protease Inhibitors against <i>Plasmodium falciparum</i>, <i>Trypanosoma brucei</i>, and <i>Trypanosoma cruzi</i>
  作者：Doron C. Greenbaum、Zachary Mackey、Elizabeth Hansell、Patricia Doyle、Jiri Gut、Conor R. Caffrey、Julia Lehrman、Philip J. Rosenthal、James H. McKerrow、Kelly Chibale

  DOI：10.1021/jm030549j

  日期：2004.6.1

  We have synthesized a library of thiosemicarbazones and screened them against three parasitic cysteine proteases, cruzain, falcipain-2, and rhodesain, and against the respective parasite sources of these three proteases, Trypanosoma cruzi, Plasmodium falciparum, and Trypanosoma brucei. The screens identified compounds that were effective against the enzymes and the parasites but also some compounds that were parasiticidal despite a lack of activity against the proteases. Several compounds were effective in killing all tested parasites. These promising lead compounds were tested for general toxicity in mice, and only one produced observable toxicity after 62 h. Our results suggest that thiosemicarbazones represent validated drug leads that kill several species of protozoan parasites through the inhibition of cysteine proteases as well as other novel targets.