1-[(4,4-dimethylthiosemicarbazono)methyl]-2-naphthol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(4,4-dimethylthiosemicarbazono)methyl]-2-naphthol
• 英文别名: N44mT；(E)-2-((2-Hydroxynaphthalen-1-yl)methylene)-N,N-dimethylhydrazine-1-carbothioamide；3-[(E)-(2-hydroxynaphthalen-1-yl)methylideneamino]-1,1-dimethylthiourea
• 化学式: C₁₄H₁₅N₃OS
• 分子量: 273.359
• InChiKey: GXWCRFKQRHUBRZ-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  80
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(4,4-dimethylthiosemicarbazono)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：

  4,4-二甲基-3-氨基硫脲单水合物 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 生成 1-[(4,4-dimethylthiosemicarbazono)methyl]-2-naphthol
  参考文献：
  名称：

  Four cytotoxic N4-substituted thiosemicarbazones derived from 2-hydroxynaphthalene-1-carboxaldehyde

  摘要：

  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，C14H15N3OS-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。

  DOI：

  10.1107/s0108270103021401

文献信息

• [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.