4,4'-dichloro-3,3'-diquinolinyl sulfide | 156153-01-4

• 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: 4,4'-dichloro-3,3'-diquinolinyl sulfide
• 英文别名: 4-Chloro-3-(4-chloroquinolin-3-yl)sulfanylquinoline
• CAS: 156153-01-4
• 化学式: C₁₈H₁₀Cl₂N₂S
• 分子量: 357.263
• InChiKey: OWJMPPKYHQTIEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  472.2±45.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 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：

  4,4'-dichloro-3,3'-diquinolinyl sulfide 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 生成 3,3'-Thio-bis-(1,4-dihydrochinolin-4-thion)
  参考文献：
  名称：

  硫桥接二磷酸酯的制备及反应行为

  摘要：

  从甲苯磺酰化的烯胺酮 5 开始，可以用乙酸、磺酰氯和亚硫酰氯制备新的喹诺酮衍生物 3、8、9 和 10。硫桥联双喹啉酮 8 烷基化得到 N-烷基产物 11 和 12。8 脱水生成新的杂环 13。化合物 8 与 POCl3 生成 4-氯喹啉衍生物 14，亚砜 15 可从准备好了。化合物 14 与硫脲反应形成异硫脲盐 16。这可以通过加热或通过硫酮 17 在 H2S 消除后转化为二硫代二喹啉 18。

  DOI：

  10.1002/ardp.19953280104
• 作为产物：
  描述：

  4,4'-dimethylthio-3,3'-diquinolinyl sulfide 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以70%的产率得到4,4'-dichloro-3,3'-diquinolinyl sulfide
  参考文献：
  名称：

  Pluta, Krystian; Maslankiewicz, Andrzej; Zieba, Andrzej, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 2, p. 447 - 452

  摘要：

  DOI：

文献信息

• 14-Substituted Diquinothiazines as a New Group of Anticancer Agents
  作者：Małgorzata Jeleń、Krystian Pluta、Małgorzata Szmielew、Beata Morak-Młodawska、Kinga Herman、Klaudia Giercuszkiewicz、Anna Kasprzycka、Magdalena Skonieczna

  DOI：10.3390/molecules28073248

  日期：——

  A series of novel double-angularly condensed diquinothiazines with aminoalkyl, amidoalkyl, sulfonamidoalkyl, and substituted phenyl groups was designed, synthesized, and evaluated for their anticancer activity against four selected human tumor cell lines (HTC116, SH-SY5Y, A549, and H1299). The cytotoxicity of the novel diquinothiazines was investigated against BEAS-2B cells. The activities of the compounds

  设计、合成了一系列具有氨基烷基、酰氨基烷基、磺酰氨基烷基和取代苯基的新型双角缩合二喹噻嗪，并评估了它们对四种选定的人类肿瘤细胞系（HTC116、SH-SY5Y、A549 和 H1299）的抗癌活性. 研究了新型二喹噻嗪对 BEAS-2B 细胞的细胞毒性。将化合物的活性与依托泊苷进行比较。其中，具有氨基烷基和苯基的化合物表现出优异的广谱抗癌活性。活性最强的 14-(甲基硫代苯基)二喹噻嗪 3c 对 BEAS-2B 细胞表现出低细胞毒性，对肿瘤细胞系 HTC116、SH-SY5Y、A549 和 H1299 表现出高活性，IC50 值为 2.3 µM、2.7 µM、17.2 µM和 2.7 µM，分别（依托泊苷分别为 8.6 µM、3.9 µM、44.8 µM 和 0.6）。还使用起始分子 M0 对细胞存活进行了实时的长期显微镜观察。流式细胞术显示了所研究的二喹噻嗪的促凋亡作用。观察到 S 期细胞周期受到抑制，这与核酸损伤有关，并与
• <i>N,N</i>-DIALKYLAMINOALKYL SUBSTITUTED QUINOBENZO[1,4]THIAZINES AND DIQUINO[1,4]THIAZINES#
  作者：K. Pluta、A. Maślankiewicz、M. Szmielew

  DOI：10.1080/10426500008043652

  日期：2000.4.1

  12-(N, N-Dialkylaminoalkyl)quino[1,4]benzothiazines 2c-2g were obtained by alkylation of 12H-quino[1,4]benzothiazines 2a and 2b with N,N-dialkylaminoalkyl chlorides in dioxane. 14H-Diquino[1,4]thiazine 4a was unreactive in the same conditions. 14-(N,N-Dialkylaminoalkyl)diquino[1,4]thiazines 4b-4d were synthesized in the annulation of 4,4'-dichloro-3,3'-diquinolinyl sulfide 3 with alkanediamines in hot phenol.
• 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.
• Pluta, Krystian; Maslankiewicz, Andrzej; Zieba, Andrzej, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 2, p. 447 - 452
  作者：Pluta, Krystian、Maslankiewicz, Andrzej、Zieba, Andrzej

  DOI：——

  日期：——
• SYNTHESIS AND PROPERTIES OF 14-SUBSTITUTED 1,4- THIAZINODIQUINOLINES
  作者：Krystian Pluta

  DOI：10.1080/10426509708043554

  日期：1997.7.1

  4,4'-Dichloro-3,3'-diquinolinyl sulfide 1 reacted with aryl-, heteroaryl- and alkylamines in MEDG or phenol to Ii-substituted thiazino[2,3-c;6,5-c']diquinolines 2. Reaction with ammonia, ammonium carbonate or benzylamine led to unsubstituted thiazine 2a. Alkylation of thiazine 2a with alkyl halides gave 14-alkyl-I,4-thiazinodiquinolines 2b, 2c and 2f. The nature of the 14-substituent has a significant effect on H-1 NMR and MS spectral properties.