2,3-dihydronaphtho[2,3-b][1,4]dithiine-5,10-dione | 10251-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-dihydronaphtho[2,3-b][1,4]dithiine-5,10-dione
• 英文别名: 2,3-Dihydronaphtho(2,3-b)(1,4)dithiine-5,10-dione；2,3-dihydrobenzo[g][1,4]benzodithiine-5,10-dione
• CAS: 10251-80-6
• 化学式: C₁₂H₈O₂S₂
• 分子量: 248.326
• InChiKey: IVQJELKILULDFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2,3-dihydronaphtho[2,3-b][1,4]dithiine-5,10-dione 在 吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 55.0h， 生成 [10-(Dicyanomethylidene)-2,3-dihydrobenzo[g][1,4]benzodithiin-5-ylidene]cyanamide
  参考文献：
  名称：

  New electron acceptors: synthesis, electrochemistry, and radical anions of N,7,7-tricyanoquinomethanimines and x-ray crystal structures of the trimethyl and tetramethyl derivatives

  摘要：

  The reaction of a range of quinones 3 with malononitrile in the presence of titanium tetrachloride/pyridine yields dicyanoquinomethides 4, which on reaction with N,N'-bis(trimethylsilyl)carbodiimide are converted into the corresponding N,7,7-tricyanoquinomethanimines 6. The solution electrochemical redox properties of compounds 6 have been studied by cyclic voltammetry; they are strong acceptors which readily form radical anions and dianions. The radical anions of N,7,7-tricyanoquinodimethanimine 6a and the tetra-, tri- and dimethyl derivatives 6c, 6d, and 6e, respectively, have been studied by ESR and ENDOR spectroscopy. X-ray crystal structure analysis reveals that trimethyl derivative 6d is planar, whereas the tetramethyl derivative 6c is strongly deformed with the ring existing in a boat conformation, similar to that found previously for tetrasubstituted TCNQ derivatives.

  DOI：

  10.1021/jo00032a017
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 1,2-乙二硫醇 以 甲醇 为溶剂， 生成 2,3-dihydronaphtho[2,3-b][1,4]dithiine-5,10-dione
  参考文献：
  名称：

  合成萘醌衍生物作为卵巢癌抗癌剂：细胞毒性测定和可能的生物学作用机制研究

  摘要：

  在这项研究中，使用简单、快速和低成本的方法合成了八种萘醌衍生物，产率在 52% 到 96% 之间。筛选了所有萘醌衍生物对 OVCA A2780 癌细胞系的体外抗增殖活性。在所有分析的化合物中，衍生物3 – 5具有最突出的细胞毒性潜力。带有含硫基团的萘醌3和4被确定为具有产生 ROS 的高潜力，特别是超氧阴离子。此外，3和4化合物导致 G0/G1 期细胞群减少，并诱导超过 90% 的细胞群发生凋亡。化合物5在这些过程中没有任何作用。最后，测试了化合物3 – 5对 PI3K 和 MAPK 的抑制能力。化合物3和4不抑制 PI3K 酶。另一方面，萘醌-多酚5只能抑制表达 pERK 的细胞百分比。

  DOI：

  10.1002/cbdv.202200807

文献信息

• 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。
• Synthesis and biological evaluation of novel 1,4-naphthoquinone derivatives as antibacterial and antiviral agents
  作者：Vishnu K. Tandon、Dharmendra B. Yadav、Ravindra V. Singh、Meenu Vaish、Ashok K. Chaturvedi、Praveen K. Shukla

  DOI：10.1016/j.bmcl.2005.04.075

  日期：2005.7

  A series of 1,4-naphthoquinone derivatives were synthesized and evaluated for antibacterial and antiviral activities. The structure-activity relationships of these compounds were also studied. The results suggest that compounds 9-22 showed in vitro marked antibacterial activity. Compounds 4c and 7a showed inhibitory effect against RNA dependent RNA polymerase induced poliovirus type 2 infected HeLa cells. (c) 2005 Elsevier Ltd. All rights reserved.
• Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones
  作者：Mark D. Cannatelli、Arthur J. Ragauskas

  DOI：10.1016/j.molcatb.2015.05.016

  日期：2015.9

  Laccases (benzenediol:oxygen oxidoreductase EC 1.10.3.2) belong to the family of multicopper oxidases. These environmentally friendly enzymes require O-2 as their only co-substrate and produce H2O as their sole by-product. As a result, they have acquired increasing use in biotechnological applications, particularly in the field of organic synthesis. In the current study, laccases have been employed to successfully couple 1,2-ethanedithiol to various substituted hydroquinones to produce novel 2,3-ethylenedithio-1,4-quinones in good yields via an oxidation-addition-oxidation-addition-oxidation mechanism. The reactions proceeded in one-pot under mild conditions (room temperature, pH 5.0). This study further supports the use of laccases as green tools in organic chemistry. Furthermore, it provides evidence that laccase-catalyzed cross-coupling reactions involving small thiols are possible, in spite of research that suggests small thiols are potent inhibitors of laccases. (C) 2015 Elsevier B.V. All rights reserved.
• Synthesis, Antitumor Activity and Docking of 2,3-(Substituted)-1,4-Naphthoquinone Derivatives Containing Nitrogen, Oxygen and Sulfur
  作者：Maicon Delarmelina、Renata D. Daltoé、Murilo F. Cerri、Klesia P. Madeira、Leticia B. A. Rangel、Valdemar Lacerda Júnior、Wanderson Romão、Alex G. Taranto、Sandro J. Greco

  DOI：10.5935/0103-5053.20150157

  日期：——

  Eleven 2,3-(substituted)-1,4-naphthoquinone derivatives were synthesized in yields ranging from 52-89%. These derivatives were evaluated for their cytotoxic effects on human lungs (H460), triple-negative breast (MDA-MB-231) and ovarian (A2780) cancer cell lines. Compounds 5f and 8 showed IC50 values of 3.048 x 10(-5) mol L-1 and 4.24 x 10(-6) mol L-1 for H460; 5c and 8 showed IC50 values of 2.16 x 10(-5) mol L-1 and 1.60 x 10(-5) mol L-1 for MDA-MB-231, and 5g and 8 showed IC50 values of 2.68 x 10(-6) mol L-1 and 3.89 x 10(-6) mol L-1 for A2780. Additionally, we conducted a docking study with the four most active compounds and the therapeutic targets PI3K and topoisomerase II showing the pharmacophoric conformation of these compounds.
• CHEMICAL AGENTS FOR THE PREVENTION OF INHIBITION OR TUMOR METASTASIS
  申请人：Bresnick Anne R.

  公开号：US20130090355A1

  公开（公告）日：2013-04-11

  The present invention provides methods of preventing or inhibiting tumor metastasis in a subject by administering a therapeutically effective amount of (1) a compound from a group of enumerated compounds, or a pharmaceutically acceptable salt thereof; (2) an agent that covalently modifies at least one cysteine residue of S100A4 protein; or (3) an agent that inhibits the interaction between S100A4 and myosin-IIA.