5,12-diaza-6,13-dithiapentacene | 68844-44-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5,12-diaza-6,13-dithiapentacene
• 英文别名: Diquino-1,4-dithiin；2,13-dithia-4,15-diazapentacyclo[12.8.0.03,12.05,10.016,21]docosa-1(22),3,5,7,9,11,14,16,18,20-decaene
• CAS: 68844-44-0
• 化学式: C₁₈H₁₀N₂S₂
• 分子量: 318.423
• InChiKey: FATSIXYTRDHHES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,12-diaza-6,13-dithiapentacene 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 2,3'-dimethylthio-2',3-diquinolinyl sulfide
  参考文献：
  名称：

  Nowak, Malgorzata; Pluta, Krystian; Kloc, Christian, Heterocycles, 2003, vol. 60, # 9, p. 2045 - 2056

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴-2-氯喹啉 在 硫脲 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 5,12-diaza-6,13-dithiapentacene
  参考文献：
  名称：

  Nowak, Malgorzata; Pluta, Krystian; Kloc, Christian, Heterocycles, 2003, vol. 60, # 9, p. 2045 - 2056

  摘要：

  DOI：

文献信息

• Synthesis of Quinobenzo-1,4-thiazines from Diquino-1,4-dithiin and 2,2’-Dichloro-3,3’-diquinolinyl Disulfide
  作者：Krystian Pluta、Małgorzata Jeleń

  DOI：10.3987/com-09-11736

  日期：——

  10-substituted quinobenzo-1,4-thiazines (benzo[b]-1-azaphenothiazines) (5) and (10), has been worked out from diquino-1,4-dithiin (5,12-diaza-6,13-dithiapentacene) (2) as fusion reactions with aniline hydrochlorides (8)·HCl via the 1,4-dithiin ring opening and the 1,4-thiazine ring closure. The better results were obtained when 2,2'-dichloro-3,3'-diquinolinyl disulfide (9) reacted with anilines (8) in MEDG

  合成新型四环氮杂吩噻嗪，6-, 8-, 9- 和 10-取代的 quinobenzo-1,4-thiazines (benzo[b]-1-azaphenothiazines) (5) 和 (10), 从diquino-1,4-dithiin (5,12-diaza-6,13-​​dithiapentacene) (2) 通过 1,4-dithiin 开环和 1,4-thiazine 与盐酸苯胺 (8)·HCl 发生融合反应闭环。当 2,2'-二氯-3,3'-二喹啉基二硫化物 (9) 与苯胺 (8) 在 MEDG 中反应时，获得了更好的结果。选择的 6H-quinobenzo-1,4-thiazines (5a) (5c) 和 (5g) 通过使用烷基卤化物的 N-烷基化转化为 6-烷基衍生物 (10a-10n)。6-甲基衍生物（10a）的同核NOE实验证实产物结构为醌[3,2-b]苯并[1,4]噻嗪。
• Synthesis of new pentacyclic diquinothiazines
  作者：Małgorzata Nowak、Krystian Pluta、Kinga Suwińska、Leo Straver

  DOI：10.1002/jhet.5570440307

  日期：2007.5

  Reactions of 2,2′-dichloro-3,3′-diquinolinyl sulfide 1 with ammonia derivatives and various primary alkylamines and arylamines proceeded as a thiazine ring closure to form linear annulated pentacyclic 6H-diquinothiazine 2H and 6-substituted derivatives 2 with alkyl, alkylaryl, aryl and heteroaryl substituents in moderate to good yields. Reaction with 2-chloroethylamine did not stop at the formation

  2,2'-二氯-3,3'-二喹啉基硫化物1与氨衍生物以及各种伯烷基胺和芳基胺的反应以噻嗪环封闭方式进行，形成线性环化的五环6 H-二喹噻嗪2H和6-取代的衍生物2与烷基，烷基芳基，芳基和杂芳基取代基的产率中等至良好。与2-氯乙胺的反应并未停止于半芥末衍生物2k的形成，而是生成了亚乙基二喹硫唑鎓盐11。6 ħ -Diquinothiazine 2H是Ñ烷基化和Ñ -arylated，得到6-取代的衍生物2。关键的底物1是通过1，4-二硫杂环丁烷的开环和进一步的转化从其他杂戊烯3和4 获得的。对-硝基苯基二喹噻嗪2i的X射线分析显示出意外的平面噻嗪环。
• Synthesis of novel heteropentacenes containing nitrogen, sulfur and oxygen or selenium
  作者：Małgorzata Nowak、Krystian Pluta、Kinga Suwińska

  DOI：10.1039/b202107m

  日期：——

  to form six linear annelated pentacyclic heterocycles with a sulfur-containing central ring (1,4-dithiin, 1,4-thiazine, 1,4-thiaselenin, 1,4-oxathiin and thiopyran) in moderate to good yields. The X-ray study of selected heteropentacenes revealed that heteropentacenes, in contrast to homopentacene, are non-planar and folded along the central sulfur-heteroatom axis. The central six-membered ring is

  2,2'-二氯-3,3'-二喹啉基硫与选定的S-，O-，Se-，C-和N-亲核试剂的反应以杂环封闭方式进行，从而形成六个带有硫的线性退火五环杂环含中心环（1,4-二硫精， 1,4-噻嗪， 1,4-硫代木素， 1,4-草胺素 和 硫吡喃）以中等到良好的产量。选定的杂戊烯的X射线研究表明，与高并五苯相反，杂戊烯是非平面的，并沿中心硫-杂原子轴折叠。中央的六元环呈船形。
• Synthesis of quinoline/naphthalene-containing azaphenothiazines and their potent in vitro antioxidant properties
  作者：Małgorzata Jeleń、Eugenia I. Bavavea、Maria Pappa、Angeliki P. Kourounakis、Beata Morak-Młodawska、Krystian Pluta

  DOI：10.1007/s00044-014-1247-y

  日期：2015.4

  New tetracyclic and pentacyclic azaphenothiazines containing one or two quinoline rings instead of benzene rings were obtained in the original reactions of isomeric diquinodithiins, dichlorodiquinolinyl sulfides, and disulfide with aromatic amines. The type of ring fusion in the azaphenothiazine system was concluded from the H-1 NMR spectra. The obtained azaphenothiazines were evaluated in vitro for their antioxidant activity on rat hepatic microsomal membranes for protection of non-enzymatic lipid peroxidation promoted by the Fe2+/ascorbic acid redox system. Most compounds exhibited a very significant antioxidant activity with IC50 values between 1 and 23 mu M. The degree of antioxidant activity depends on the lipophilicity and molecular size as well as the (non)substitution of the thiazine nitrogen atom and type of ring system fusion. It is the first time to our knowledge that azaphenothiazines are shown to exhibit such potent antioxidant activity.
• Reaction of thionyl chloride with 3,4-dihydro-2(1H)-quinolinone
  作者：Barry A. Dreikorn、A. Frederick Elsasser、Glen P. Jourdan

  DOI：10.1021/jo01319a056

  日期：1979.3