2,2'-dichloro-3,3'-diquinolinyl sulfide | 68844-43-9

• 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 sulfide
• 英文别名: 2,2'-dichloro-3,3'-diquinolinylsulfide；2,2'-dichloro-3,3'-sulfanediyl-bis-quinoline；3,3'-Thiobis-(2-chlorchinolin)；Quinoline, 3,3'-thiobis[2-chloro-；2-chloro-3-(2-chloroquinolin-3-yl)sulfanylquinoline
• CAS: 68844-43-9
• 化学式: C₁₈H₁₀Cl₂N₂S
• 分子量: 357.263
• InChiKey: RFKCKWRWLQHLJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2'-dichloro-3,3'-diquinolinyl sulfide 在 硒脲 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 1.0h， 以81%的产率得到1,4-thiaselenini[3,2-b;5,6-b']diquinoline
  参考文献：
  名称：

  含氮，硫，氧或硒的新型杂戊烯的合成

  摘要：

  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。

  DOI：

  10.1039/b202107m
• 作为产物：
  描述：

  3-[(2-oxo-1H-quinolin-3-yl)sulfanyl]-1H-quinolin-2-one 在 三氯氧磷 作用下， 反应 1.0h， 以94%的产率得到2,2'-dichloro-3,3'-diquinolinyl sulfide
  参考文献：
  名称：

  含氮，硫，氧或硒的新型杂戊烯的合成

  摘要：

  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。

  DOI：

  10.1039/b202107m

文献信息

• Synthesis of 6-Aminoalkyldiquino-1,4-thiazines and Their Acyl and Sulfonyl Derivatives
  作者：Krystian Pluta、Malgorzata Jelen

  DOI：10.3987/com-07-11269

  日期：——

  primary amines, and 6H-diquino-1,4-thiazine (4) with dialkylaminoalkyl chlorides and phthalimidoalkyl bromides followed by hydrolysis. 6-Aminoalkyldiquinothiazines (11-13) were transformed into acyl and sulfonyl derivatives (15-26). Some of the obtained compounds showed significant anticancer activity.

  在 diquino-1,4-dithiin (2) 和 2 的反应中阐述了各种 6-二烷基氨基烷基二醌-1,4-噻嗪 (5-8) 和 6-氨基烷基二醌-1,4-噻嗪 (11-13) 的合成,2'-二氯-3,3'-二喹啉硫醚 (3) 与伯胺，以及 6H-二喹啉-1,4-噻嗪 (4) 与二烷基氨基烷基氯化物和邻苯二甲酰亚胺烷基溴，然后水解。6-氨基烷基二喹噻嗪 (11-13) 被转化为酰基和磺酰基衍生物 (15-26)。一些获得的化合物显示出显着的抗癌活性。
• 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 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.
• ——
  作者：Krystian Pluta、Małgorzata Nowak、Kinga Suwińska

  DOI：10.1023/a:1011307717972

  日期：——

  The title compound (C24H15N3S) is monoclinic, with a = 10.816(1), b = 8.193(1), c = 10.892(1), beta = 104.20(1)degrees and space group P2(1). The molecule is folded with the central ring, in a boat conformation. It can also be considered as folded around the C-C axis between the thiazine and pyridine rings. The butterfly folding angle between the two quinoline planes is 20.5(1)degrees and between the planes of the two halves of the thiazine ring is 30.6(1)degrees. The phenyl substituent is in an equatorial location with respect to the thiazine ring with the C-N . . .S angle of 163.0(2)degrees. The phenyl plane nearly bisects the pentacyclic ring system and is nearly perpendicular to the C(2), C(3), C(12), C(13) plane.
• DREIKORN B. A.; ELSASSER A. F.; JOURDAN G. P., J. ORG. CHEM., 1979, 44, NO 5, 877-880
  作者：DREIKORN B. A.、 ELSASSER A. F.、 JOURDAN G. P.

  DOI：——

  日期：——