6-((10H-phenothiazin-10-yl)methyl)-2-(4-chlorophenyl)-5,6,7,8-tetrahydro-2H-tetrazolo[5,1-f][1,2]azaborinin-4-ium-5-uide | 1256974-11-4

• 英文名称: 6-((10H-phenothiazin-10-yl)methyl)-2-(4-chlorophenyl)-5,6,7,8-tetrahydro-2H-tetrazolo[5,1-f][1,2]azaborinin-4-ium-5-uide
• CAS: 1256974-11-4
• 化学式: C₂₃H₂₁BClN₅S
• 分子量: 445.783
• InChiKey: PPUSLWQWUIBACB-UHFFFAOYSA-N

物化性质

• 熔点：
  166-168 °C(Solvent: Hexane; Diethyl ether)

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  6-((10H-phenothiazin-10-yl)methyl)-2-(4-chlorophenyl)-5,6,7,8-tetrahydro-2H-tetrazolo[5,1-f][1,2]azaborinin-4-ium-5-uide 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 以0.66 g的产率得到4-(2-(4-chlorophenyl)-2H-tetrazol-5-yl)-1-(10H-phenothiazin-10-yl)butan-2-ol
  参考文献：
  名称：

  Selective hydroboration of dieneamines. Formation of hydroxyalkylphenothiazines as MDR modulators

  摘要：

  N-dienylphenothiazines synthesized from tetrazolo[1,5-a]pyridinium salts by treatment with phenothiazine were subjected to catalytic hydrogenation to yield N-butylphenothiazines, whereas transformation of these dienes with borane dimethyl sulfide (BH3 x Me2S) resulted in selective hydroboration of one double bond and full reduction of the other double bond to give 2-hydroxybutylphenothiazines. Position of the hydroxyl group was supported by NMR spectroscopy and verified by X-ray analysis. Comparison of MDR modulatory activity of the new derivatives revealed that the hydroxybutyl compounds are promising candidates for development of novel MDR inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.065
• 作为产物：
  描述：

  10-((1E,3Z)-4-(2-(4-chlorophenyl)-2H-tetrazol-5-yl)buta-1,3-dien-1-yl)-10H-phenothiazine 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 6-((10H-phenothiazin-10-yl)methyl)-2-(4-chlorophenyl)-5,6,7,8-tetrahydro-2H-tetrazolo[5,1-f][1,2]azaborinin-4-ium-5-uide
  参考文献：
  名称：

  Selective hydroboration of dieneamines. Formation of hydroxyalkylphenothiazines as MDR modulators

  摘要：

  N-dienylphenothiazines synthesized from tetrazolo[1,5-a]pyridinium salts by treatment with phenothiazine were subjected to catalytic hydrogenation to yield N-butylphenothiazines, whereas transformation of these dienes with borane dimethyl sulfide (BH3 x Me2S) resulted in selective hydroboration of one double bond and full reduction of the other double bond to give 2-hydroxybutylphenothiazines. Position of the hydroxyl group was supported by NMR spectroscopy and verified by X-ray analysis. Comparison of MDR modulatory activity of the new derivatives revealed that the hydroxybutyl compounds are promising candidates for development of novel MDR inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.065

文献信息

• Formation of a new ring system: Tetrazolo[5,1-f][1,2]azaborinin
  作者：Daniella Takács、Péter Király、Ildikó Nagy、Petra Bombicz、Orsolya Egyed、Zsuzsanna Riedl、György Hajós

  DOI：10.1016/j.jorganchem.2010.08.049

  日期：2010.11

  of the olefinic bond underwent reduction and, furthermore, borane addition at the double bond took place to yield derivatives of tetrazolo[5,1-f][1,2]azaborinin as a new fused ring system involving a bridge-head nitrogen atom. The new products have been synthesized and characterized by X-ray analysis, solution and solid-state NMR.

  由四氮杂吡啶鎓盐和吩噻嗪衍生物制得的吩噻嗪基二烯经THF中的硼烷-二甲基硫醚还原。产物的结构阐明表明，其中一个烯键进行了还原，此外，在双键处发生了硼烷加成反应，生成了四唑并[5,1- f ] [1,2]天青素的衍生物，作为新的稠环系统。涉及桥头氮原子。这些新产品已经合成，并通过X射线分析，溶液和固态NMR进行了表征。