6H-diquino[3,4-b;4',3'-e][1,4]thiazine | 212499-86-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6H-diquino[3,4-b;4',3'-e][1,4]thiazine
• 英文别名: 13-Thia-2,10,16-triazapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4,6,8,10,15,17,19,21-decaene
• CAS: 212499-86-0
• 化学式: C₁₈H₁₁N₃S
• 分子量: 301.371
• InChiKey: MYDLIWYFLHYJJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  63.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6H-diquino[3,4-b;4',3'-e][1,4]thiazine 、 碘甲烷 在 sodium hydride 作用下， 生成 14-methyl-1,4-thiazino[2,3-c;6,5-c']diquinoline
  参考文献：
  名称：

  SYNTHESIS AND PROPERTIES OF 14-SUBSTITUTED 1,4- THIAZINODIQUINOLINES

  摘要：

  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.

  DOI：

  10.1080/10426509708043554
• 作为产物：
  描述：

  3,3'-thiobis(4-quinolone) hydrochloride 在 三氯氧磷 作用下， 以 various solvent(s) 为溶剂， 反应 5.0h， 生成 6H-diquino[3,4-b;4',3'-e][1,4]thiazine
  参考文献：
  名称：

  SYNTHESIS AND PROPERTIES OF 14-SUBSTITUTED 1,4- THIAZINODIQUINOLINES

  摘要：

  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.

  DOI：

  10.1080/10426509708043554

文献信息

• 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.