2,2’-dichloro-3,3’-diquinolinyl disulfide | 68844-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,2’-dichloro-3,3’-diquinolinyl disulfide
• 英文别名: 2,2′-dichloro-3,3′-diquinolinyl disulfide；2,2'-dichloro-3,3'-diquinolinyl disulfide；2,2'-dichloro-3,3'-diquinolinyldisulfide；2,2'-dichloro-3,3'-disulfanediyl-bis-quinoline；3,3'-Dithiobis-(2-chlorchinolin)；2-Chloro-3-[(2-chloroquinolin-3-yl)disulfanyl]quinoline
• CAS: 68844-39-3
• 化学式: C₁₈H₁₀Cl₂N₂S₂
• 分子量: 389.329
• InChiKey: IFQQBADRCPWEOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• 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：

  2,2’-dichloro-3,3’-diquinolinyl disulfide 在 sodium tetrahydroborate 作用下， 以 正丁醇 为溶剂， 生成 5,12-diaza-6,13-dithiapentacene
  参考文献：
  名称：

  Reaction of thionyl chloride with 3,4-dihydro-2(1H)-quinolinone

  摘要：

  DOI：

  10.1021/jo01319a056
• 作为产物：
  描述：

  3,4-二氢-2(1H)-喹啉酮 、 N,N-二甲基甲酰胺 以18%的产率得到
  参考文献：
  名称：

  DREIKORN B. A.; ELSASSER A. F.; JOURDAN G. P., J. ORG. CHEM., 1979, 44, NO 5, 877-880

  摘要：

  DOI：

文献信息

• Evaluation of angularly condensed diquinothiazines as potential anticancer agents
  作者：Małgorzata Jeleń、Krystian Pluta、Małgorzata Latocha、Beata Morak-Młodawska、Kinga Suwińska、Dariusz Kuśmierz

  DOI：10.1016/j.bioorg.2019.04.005

  日期：2019.6

  We present efficient synthesis of isomeric types of angularly fused diquinothiazines in the reactions of 2,2'-dichloro-3,3'-diquinolinyl disulfide and diquinodithiin with 3-, 5-, 6- and 8-aminoquinolines. The pentacyclic diquinothiazine ring systems were identified as diquino[3,2-b;3',4'-e][1,4]thiazine, diquino[3,2-b;5',6'-e][1,4]thiazine, diquino[3,2-b;6',5'-e][1,4]thiazine and diquino[3,2-b;8',7'-e][1

  我们目前在2,2'-dichloro-3,3'-二喹啉基二硫化物和diquinodithiin与3-，5-，6-和8-氨基喹啉的反应中，高效合成了有角度融合的二喹噻嗪的异构体类型。五环二喹噻嗪环系统被确定为diquino [3,2-b; 3'，4'-e] [1,4]噻嗪，diquino [3,2-b; 5'，6'-e] [1， 4]噻嗪，二喹啉[3,2-b; 6'，5'-e] [1,4]噻嗪和二喹啉[3,2-b; 8'，7'-e] [1,4]噻嗪N-甲基衍生物的先进二维1H和13C NMR技术（COSY，ROESY，HSQC和HMBC）。通过选择的N-烷基衍生物的X射线衍射分析证实了五环系统的鉴定。X射线分析揭示了环系统的不同空间结构（平面的和折叠的）。NH-二喹噻嗪进一步被转化为N-烷基和N-二烷基氨基烷基衍生物。大部分二喹噻嗪类药物对人胶质母细胞瘤SNB-19，结直肠癌Caco-2，乳
• 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 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.
• The Structures of 8- and 10-Trifluoromethylquino[3,2-b]benzo[1,4]thiazines and Their Benzyl Derivatives
  作者：Krystian Pluta、Małgorzata Jeleń、Kinga Suwińska、Céline Besnard、Beata Morak-Młodawska

  DOI：10.3987/com-12-12528

  日期：——

  The modification of the phenothiazine structure via the substitution of the benzene ring with the quinoline ring may proceed through the Ullmann cyclization or the Smiles rearrangement of the appropriate sulfides followed by cyclization. Reactions of 2,2'-dichloro-3,3'-diquinolinyl disulfide or pentacyclic diquinodithiin with m-trifluoromethylaniline led to two isomeric tetracyclic trifluoromethylquinobenzothiazines. The product structures as the appropriate 6H-X-trifluoromethylquino[3,2-b]benzo[1,4]thiazines (X = 8, 10) were finally confirmed by X-ray analysis (one product was transformed into N-benzyl derivative). These results exclude the possibility of the reverse Smiles rearrangement and the existence of 5H-tautomers in these conditions. Although both compounds have the same quinobenzothiazine system, they differ in the spatial structures and geometric data. Molecule 6b is unexpectedly almost planar that is the result of larger than usual the C-S-C and C-N-C angles in the thiazine ring. Molecule 14 is folded along the S-N axis with the thiazine ring in boat conformation and the benzyl group in equatorial position.