2-methyl-3-(4-chlorophenylthio)-1,4-naphthalenedione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyl-3-(4-chlorophenylthio)-1,4-naphthalenedione
• 英文别名: 2-((4-chlorophenyl)thio)-3-methylnaphthalene-1,4-dione；2-(4-chloro-phenylsulfanyl)-3-methyl-[1,4]naphthoquinone；2-(4-Chlor-phenylmercapto)-3-methyl-[1,4]naphthochinon；2-(4-Chlorophenyl)sulfanyl-3-methylnaphthalene-1,4-dione；2-(4-chlorophenyl)sulfanyl-3-methylnaphthalene-1,4-dione
• 化学式: C₁₇H₁₁ClO₂S
• 分子量: 314.792
• InChiKey: XLAQIYKLJOWHJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-环氧-2,3-二氢-2-甲基-1,4-萘醌 、 4-氯苯硫酚 在 potassium hydroxide 作用下， 以 异丙醇 为溶剂， 生成 2-methyl-3-(4-chlorophenylthio)-1,4-naphthalenedione
  参考文献：
  名称：

  Characteristic solid-state color properties and crystal structures of 2-methyl-3-chlorophenylthio-1,4-naphthalenedione

  摘要：

  The novel compounds 2-methyl-3-(2-chlorophenylthio)-1,4-naphthalenedione and 2-methyl-3-(3-chlorophenylthio)-1,4-naphthalenedione were successfully synthesized. Although the color of three types of 2-methyl-3-[2-chloro (or 3-chloro or 4-chloro)phenylthio]-1,4-naphthalenedione in solution are similar, the solid-state color of these compounds could be easily changed according to the position of the chloro group in the phenylthio ring. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.10.001

文献信息

• [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。
• Visible Light-Mediated Thiolation of Substituted 1,4-Naphthoquinones Using Eosin Y as a Photoredox Catalyst
  作者：Bhawana Nagar、Basab Bijayi Dhar

  DOI：10.1021/acs.joc.1c02924

  日期：2022.3.4

  (isolated yield of ≥75%) for thiolation of substituted 1,4-naphthoquinones using various aromatic and aliphatic thiols at room temperature is described herein. The rate-determining step of the reaction is thiyl radical generation, and the radical was characterized by high-resolution mass spectrometry. Cost effectiveness, operational simplicity, a short reaction time, high atom economy, and a very good yield

  在伊红 Y 存在下，本文描述了在室温下使用各种芳香族和脂肪族硫醇对取代的 1,4-萘醌进行硫醇化的可见光诱导的一步程序（分离产率≥75%）。该反应的限速步骤是硫自由基的产生，该自由基通过高分辨质谱进行表征。成本效益、操作简单、反应时间短、原子经济性高和非常好的产率使得这种光氧化还原介导的过程成为过渡金属（例如，Cu、Ag 和 Pd）催化的醌与硫醇或二硫化物。
• Control of relationship between conformational and color polymorphs of achiral 2-methyl-3-arylthio-1,4-naphthalenediones
  作者：Takafumi Kinuta、Tomohiro Sato、Takunori Harada、Nobuo Tajima、Reiko Kuroda、Yoshio Matsubara、Yoshitane Imai

  DOI：10.1016/j.molstruc.2010.07.032

  日期：2010.10

  The achiral compound 2-methyl-3-(4-bromophenylthio)-1,4-naphthalenedione shows conformational and color polymorphism. The relationship between the conformational and color polymorphs (chirality and color) of 2-methyl-3-arylthio-1,4-naphthalenediones can change according to the type of arylthio group. (C) 2010 Elsevier B.V. All rights reserved.
• Naphthoquinone Antimalarials. XXIII. Bz-Substituted Derivatives
  作者：Louis F. Fieser、Russell H. Brown

  DOI：10.1021/ja01179a010

  日期：1949.11.19