6-((2-chloro-10H-phenothiazin-10-yl)methyl)-2-(4-methoxyphenyl)-5,6,7,8-tetrahydro-2H-tetrazolo[5,1-f][1,2]azaborinin-4-ium-5-uide | 1387626-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 6-((2-chloro-10H-phenothiazin-10-yl)methyl)-2-(4-methoxyphenyl)-5,6,7,8-tetrahydro-2H-tetrazolo[5,1-f][1,2]azaborinin-4-ium-5-uide
• CAS: 1387626-94-9
• 化学式: C₂₄H₂₃BClN₅OS
• 分子量: 475.81
• InChiKey: NTBPQWBFQUBDAE-UHFFFAOYSA-N

物化性质

• 熔点：
  153-157 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  47.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3-(4-methoxyphenyl)-tetrazolo[1,5-a]pyridin-4-ium tetrafluoroborate 在 dimethyl sulfide borane 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 72.33h， 生成 6-((2-chloro-10H-phenothiazin-10-yl)methyl)-2-(4-methoxyphenyl)-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