1-[(4-ethylthiosemicarbazono)methyl]-2-naphthol | 284683-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(4-ethylthiosemicarbazono)methyl]-2-naphthol
• 英文别名: (E)-N-ethyl-2-((2-hydroxynaphthalen-1-yl)methylene)hydrazinecarbothioamide；N4eT；2-Hydroxy-1-naphthaldehyde N-ethylthiosemicarbazone；1-ethyl-3-[(E)-(2-hydroxynaphthalen-1-yl)methylideneamino]thiourea
• CAS: 284683-88-1
• 化学式: C₁₄H₁₅N₃OS
• 分子量: 273.359
• InChiKey: IDWSYZMSXOBZMW-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1-[(4-ethylthiosemicarbazono)methyl]-2-naphthol 、 copper diacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Increased generation of intracellular reactive oxygen species initiates selective cytotoxicity against the MCF-7 cell line resultant from redox active combination therapy using copper–thiosemicarbazone complexes

  摘要：

  The combination of cytotoxic copper-thiosemicarbazone complexes with phenoxazines results in an up to 50-fold enhancement in the cytotoxic potential of the thiosemicarbazone against the MCF-7 human breast adenocarcinoma cell line over the effect attributable to drug additivity-allowing minimization of the more toxic copper-thiosemicarbazone component of the therapy. The combination of a benzophenoxazine with all classes of copper complex examined in this study proved more effective than combinations of the copper complexes with related isoelectronic azines. The combination approach results in rapid elevation of intracellular reactive oxygen levels followed by apoptotic cell death. Normal fibroblasts representative of non-cancerous cells (MRC-5) did not display a similar elevation of reactive oxygen levels when exposed to similar drug levels. The minimization of the copper-thiosemicarbazone component of the therapy results in an enhanced safety profile against normal fibroblasts.

  DOI：

  10.1007/s00775-016-1350-2
• 作为产物：
  描述：

  4-乙基-3-硫代氨基脲 、 2-羟基-1-萘甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以71%的产率得到1-[(4-ethylthiosemicarbazono)methyl]-2-naphthol
  参考文献：
  名称：

  缩氨基硫脲的体外抗氧化、抗炎和硅分子对接研究

  摘要：

  摘要 5-甲氧基水杨醛/2-羟基-1-萘醛与(un)反应得到了一系列5-甲氧基水杨醛附加氨基硫脲(1-4)和2-羟基-1-萘醛附加氨基硫脲(5-8)。氨基硫脲衍生物的 N 末端位置的取代变化所带来的生物学特性。通过元素分析和各种光谱技术（紫外-可见光、红外光谱、核磁共振和质谱）对化合物进行了全面表征。三种化合物（1、2 和 7）的固态结构通过单晶 X 射线衍射法测定。化合物(1、2和7)采用具有P21/c(1和2)或C2/c(7)空间群的单斜晶系。分别通过体外 DPPH 和溶血试验分析了化合物 (1-8) 的抗氧化和非溶血活性。抗炎潜力通过体外 PLA2 抑制试验和计算机分子对接研究得到验证。体外和计算机研究揭示了缩氨基硫脲衍生物有希望的抗炎潜力。化合物 2、4、6、7 和 8 显示出显着的抗炎活性。

  DOI：

  10.1016/j.molstruc.2017.05.054

文献信息

• Four cytotoxic N4-substituted thiosemicarbazones derived from 2-hydroxynaphthalene-1-carboxaldehyde
  作者：Paul V. Bernhardt、Lorraine M. Caldwell、David B. Lovejoy、Des R. Richardson

  DOI：10.1107/s0108270103021401

  日期：2003.11.1

  The X-ray crystal structures are reported of four novel and potentially O,N,S-tridentate donor ligands that demonstrate antitumour activity. These ligands are 1-[(4-methylthiosemicarbazono)methyl]-2-naphthol, C₁₃H₁₃N₃OS, (III), 1-[(4-ethylthiosemicarbazono)methyl]-2-naphthol, C₁₄H₁₅N₃OS, (IV), 1-[(4-phenylthiosemicarbazono)methyl]-2-naphthol, C₁₈H₁₅N₃OS, (V), and 1-[(4,4-dimethylthiosemicarbazono)methyl]-2-naphthol dimethyl sulfoxide solvate, C₁₄H₁₅N₃OS·C₂H₆OS, (VI). These chelators are N4-substituted thiosemicarbazones, each based on the same parent aldehyde, namely 2-zhydroxynaphthalene-1-carboxaldehyde isonicotinoylhydrazone. Conformational variations within this series are discussed in relation to the optimum conformation for metal-ion binding.

  报告了四种新型和潜在的 O、N、S-三叉供体配体的 X 射线晶体结构，这些配体具有抗肿瘤活性。这些配体是 1-[(4-甲基硫代氨基羰基)甲基]-2-萘酚，C13H13N3OS，(III)；1-[(4-乙基硫代氨基羰基)甲基]-2-萘酚，C14H15N3OS，(IV)、1-[（4-苯基thiOSemicarbazono）甲基]-2-萘酚，C18H15N3OS，（V），以及 1-[（4,4-二甲基thiOSemicarbazono）甲基]-2-萘酚二甲亚砜溶液， OS-C2H6OS，（VI）。这些螯合剂都是 N4 取代的硫代氨基甲酰肼，每一种都基于相同的母醛，即 2-氮羟基萘-1-甲醛异烟酰腙。该系列中的构象变化与金属离子结合的最佳构象有关。
• [EN] NAPHTHYLSEMICARBAZONE, NAPHTHYLHYDRAZONE, NAPHTHYLTHIOSEMICARBAZONE, AND NAPHTHYLTHIOHYDRAZONE COMPOUNDS AND THERAPEUTIC USE THEREOF<br/>[FR] DERIVES DE NAPHTHYL(THIO)SEMICARBAZONE ET LEUR UTILISATION THERAPEUTIQUE
  申请人：UNISEARCH LTD

  公开号：WO2003078386A1

  公开（公告）日：2003-09-25

  The present invention relates to novel naphthyl semicarbazone, naphthylhydrazone, naphthyl thiosemicarbazone, and naphthyl thiohydrazone compounds. The invention also relates to therapeutic uses of such compounds and/or their iron complexes. The invention further relates to methods of treating diseases associated with cell proliferation and diseases associated with microbial infection.
• [EN] METHODS FOR DIAGNOSING IRON-RELATED PATHOLOGIES<br/>[FR] PROCÉDÉS POUR LE DIAGNOSTIC DE PATHOLOGIES ASSOCIÉES AU FER
  申请人：UNIV ARIZONA STATE

  公开号：WO2015142882A1

  公开（公告）日：2015-09-24

  Methods for diagnosing or assisting in the diagnosis of iron-related pathologies are provided. The methods are based on the correlation of the degree of iron-specific hypercoagulability with clinical disease. One embodiment provides a method for diagnosing or assisting in diagnosing a subject having or suspected of having an iron-related pathology by analyzing a blood sample obtained from the subject to obtain viscoelastic parameters of the blood sample as the blood sample coagulates. A variation in the viscoelastic parameters of the blood sample relative to a blood sample from a healthy subject indicates the subject has or will likely develop an iron-related pathology. Subjects having an iron-related pathology have viscoelastic parameters that are indicative of enhanced coagulation and/or diminished fibrinolysis compared to the viscoelastic parameters of the blood sample from the healthy subject.