2-(2-羟基乙基硫代)-3-甲基萘-1,4-二酮 | 59147-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(2-羟基乙基硫代)-3-甲基萘-1,4-二酮
• 英文名称: 2-(2-hydroxyethyl)thio-3-methyl-1,4-naphthoquinone
• 英文别名: 2-(2-hydroxyethyl)thio-3-methylnaphthoquinone；NSC 672121；2-((2-Hydroxyethyl)thio)-3-methylnaphthalene-1,4-dione；2-(2-hydroxyethylsulfanyl)-3-methylnaphthalene-1,4-dione
• CAS: 59147-84-1
• 化学式: C₁₃H₁₂O₃S
• 分子量: 248.302
• InChiKey: MZIOEPIEDDJOPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090
• 储存条件：
  存储条件：2-8°C，密封保存，并保持干燥。

反应信息

• 作为反应物：
  描述：

  2-(2-羟基乙基硫代)-3-甲基萘-1,4-二酮 在 溶剂黄146 、 锌 作用下， 以 乙醚 为溶剂， 反应 0.08h， 以94%的产率得到2-(2-mercaptoethanol)-3-methyl-1,4-naphthohydroquinone
  参考文献：
  名称：

  Thioalkyl Derivatives of Vitamin K3 and Vitamin K3 Oxide Inhibit Growth of Hep3B and HepG2 Cells

  摘要：

  A new hypothesis regarding the effect of vitamin K-3 On hepatoma cell growth is presented. In brief, exploration of cell growth activity has been identified with the action of p34(cdc2) kinase and its associated protein tyrosine phosphatase. After exploring a series of substituted derivatives of vitamin K and vitamin K-3 oxide, we suggest a mechanism involving alkylation at the active-site cysteine for the inhibition of the protein tyrosine phosphatase which controls the activity of the p34(cdc2) kinase. (C) 1995 Academic Press, Inc.

  DOI：

  10.1006/bioo.1995.1008
• 作为产物：
  描述：

  2,3-环氧-2,3-二氢-2-甲基-1,4-萘醌 、 2-巯基乙醇 在 咪唑 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以85%的产率得到2-(2-羟基乙基硫代)-3-甲基萘-1,4-二酮
  参考文献：
  名称：

  Thioalkyl Derivatives of Vitamin K3 and Vitamin K3 Oxide Inhibit Growth of Hep3B and HepG2 Cells

  摘要：

  A new hypothesis regarding the effect of vitamin K-3 On hepatoma cell growth is presented. In brief, exploration of cell growth activity has been identified with the action of p34(cdc2) kinase and its associated protein tyrosine phosphatase. After exploring a series of substituted derivatives of vitamin K and vitamin K-3 oxide, we suggest a mechanism involving alkylation at the active-site cysteine for the inhibition of the protein tyrosine phosphatase which controls the activity of the p34(cdc2) kinase. (C) 1995 Academic Press, Inc.

  DOI：

  10.1006/bioo.1995.1008

文献信息

• Discovery of the First Vitamin K Analogue as a Potential Treatment of Pharmacoresistant Seizures
  作者：Xiaoyang Li、Richard A. Himes、Lyndsey C. Prosser、Charleston F. Christie、Emma Watt、Sharon F. Edwards、Cameron S. Metcalf、Peter J. West、Karen S. Wilcox、Sherine S. L. Chan、C. James Chou

  DOI：10.1021/acs.jmedchem.0c00168

  日期：2020.6.11

  Despite the availability of more than 25 antiseizure drugs on the market, approximately 30% of patients with epilepsy still suffer from seizures. Thus, the epilepsy therapy market has a great need for a breakthrough drug that will aid pharmacoresistant patients. In our previous study, we discovered a vitamin K analogue, 2h, which displayed modest antiseizure activity in zebrafish and mouse seizure

  尽管市场上有超过25种抗癫痫药，但仍有大约30％的癫痫患者患有癫痫病。因此，癫痫治疗市场非常需要一种突破性的药物来帮助对药物耐药的患者。在我们先前的研究中，我们发现了维生素K类似物2h，在斑马鱼和小鼠癫痫发作模型中显示出适度的抗癫痫发作活性。但是，由于该化合物的药代动力学特征，因此存在局限性。在这项研究中，我们通过修改2h的结构开发了一系列新的维生素K类似物。其中，化合物3d在具有有限的旋转脚马达毒性和良好的药代动力学特性的啮齿动物药物性癫痫发作模型中显示出完全的保护作用。此外，脑/血浆浓度比为3d表示其极佳的渗透性。所得数据表明3d可在临床中进一步发展为潜在的抗癫痫药。
• Oxidative radical coupling of hydroquinones and thiols using chromic acid: one-pot synthesis of quinonyl alkyl/aryl thioethers
  作者：T. P. Adarsh Krishna、Sakthivel Pandaram、Suresh Chinnasamy、Andivelu Ilangovan

  DOI：10.1039/d0ra01519a

  日期：——

  An efficient, simple and practical protocol for one-pot sequential oxidative radical C–H/S–H cross-coupling of thiols with hydroquinones (HQs) and oxidation leading to the formation of quinonyl alkyl/aryl thioethers using H2CrO4 was developed. This cross-coupling of thiyl and aryl radicals offers mono thioethers in good to moderate yield and works well with a wide variety of thiols. Similarly, this

  开发了一种高效、简单且实用的方案，用于硫醇与氢醌 (HQ) 的一锅顺序氧化自由基 C–H/S–H 交叉偶联和氧化，从而使用 H 2 CrO 4形成醌基烷基/芳基硫醚。硫基和芳基的这种交叉偶联以良好至中等的产率提供单硫醚，并且与多种硫醇配合良好。同样，该方法适用于 2-氨基苯硫酚和 HQ 的偶联形成吩噻嗪-3-酮5a–c 。首次使用铬试剂观察到通过硫醚合成形成 C-S 键。对化合物5a–c药代动力学特性的理论研究表明，由于具有药物样特性，化合物5b与阿尔茨海默病 (AD) 相关的 AChE 靶位点强烈结合。
• [EN] NAPHTHAQUINONE METHYLTRANSFERASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE NAPHTAQUINONE MÉTHYLTRANSFÉRASE ET LEURS UTILISATIONS
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2015172076A1

  公开（公告）日：2015-11-12

  Provided herein are compounds of (I), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, and prodrugs thereof. Also provided are pharmaceutical compositions and methods involving the inventive compounds for the treatment of proliferative diseases (e.g., cancer (e.g., leukemia, breast cancer, melanoma, metastatic cancer) and diseases associated with inappropriate SET8 activity. Also provided are methods for inhibiting SET8 and methods for labelling SET8.

  本文提供了化合物(I)及其药用可接受的盐、溶剂合物、水合物、多型体、共晶体、互变异构体、立体异构体和其前药。还提供了涉及创新化合物用于治疗增殖性疾病（例如，癌症（例如，白血病、乳腺癌、黑色素瘤、转移性癌症）和与不当的SET8活性相关的疾病）的药物组合物和方法。还提供了用于抑制SET8的方法和用于标记SET8的方法。
• Maleiimide anti-tumor phosphatase inhibitors
  申请人：Michejda J. Christopher

  公开号：US20080039518A1

  公开（公告）日：2008-02-14

  The present invention features maleiimide compounds, pharmaceutical compositions of maleiimide compounds and methods of treating a patient suffering from cancer, the method comprising administering to a patient one or more maleiimide compounds of the invention.

  本发明涉及maleiimide化合物、maleiimide化合物的药物组成物以及治疗患有癌症的患者的方法，该方法包括向患者施用本发明中的一个或多个maleiimide化合物。
• Site-Specific Binding of Quinones to Proteins through Thiol Addition and Addition−Elimination Reactions
  作者：Wen-Wu Li、Jürgen Heinze、Wolfgang Haehnel

  DOI：10.1021/ja050974x

  日期：2005.5.1

  Model thioether quinone conjugates showed unexpected reactivity to cysteine of proteins as their parent quinones by thiol addition-elimination reaction. Cyclic voltammetry studies of the model compounds showed only minor differences in their redox potentials as compared to their parent quinones. Thioether ligation provides a general, simple, and fast method to construct model quinone protein systems

  Ubiquinone-0、menaquinone-0 和 2,3,5-trimethyl-1,4-benzoquinone 通过硫醚键形成与蛋白质的游离半胱氨酸（酵母 iso-1 细胞色素 c 作为模型蛋白质）进行位点特异性结合。模型硫醚醌缀合物通过硫醇加成消除反应显示出对作为其母体醌的蛋白质的半胱氨酸的出乎意料的反应性。模型化合物的循环伏安法研究表明，与其母体醌相比，它们的氧化还原电位只有很小的差异。硫醚连接提供了一种通用、简单且快速的方法来构建模型醌蛋白质系统。此外，这些研究也有助于了解醌类和硫醚醌加合物的生物活性、毒性和抗癌机制。