1-[2-oxo-2-(10H-phenothiazin-10-yl)ethyl]-4-dimethylaminopyridinium chloride | 1030630-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 1-[2-oxo-2-(10H-phenothiazin-10-yl)ethyl]-4-dimethylaminopyridinium chloride
• 英文别名: 2-[4-(dimethylamino)pyridin-1-ium-1-yl]-1-phenothiazin-10-ylethanone;chloride
• CAS: 1030630-79-5
• 化学式: C₂₁H₂₀N₃OS*Cl
• 分子量: 397.928
• InChiKey: UHLSSBMUEOLOAD-UHFFFAOYSA-M

物化性质

• 熔点：
  228-230 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-oxo-2-(10H-phenothiazin-10-yl)ethyl]-4-dimethylaminopyridinium chloride 、 丙炔酸乙酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以45%的产率得到Ethyl 7-(dimethylamino)-3-(phenothiazine-10-carbonyl)indolizine-1-carboxylate
  参考文献：
  名称：

  Synthesis and anticancer activity of analogues of phenstatin, with a phenothiazine A-ring, as a new class of microtubule-targeting agents

  摘要：

  A new family of microtubule-targeting agents with a phenothiazine A-ring was synthesized and evaluated for anti-proliferative activity and interaction with tubulin. These new derivatives showed significant activities against cellular proliferation and tubulin polymerization, rather similar to those of phenstatin. Phenothiazine derivative 21 proved to be the most potent compound synthesized with GI(50) values ranging from 29 to 93 nM on different cell lines. The same compound showed a better inhibition of COLO 205, A498, and MCF7 cell lines than the parent phenstatin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.135
• 作为产物：
  描述：

  4-二甲氨基吡啶 、 10-(氯乙酰基)-10H-吩噻嗪 以 乙酸乙酯 为溶剂， 反应 24.0h， 以93%的产率得到1-[2-oxo-2-(10H-phenothiazin-10-yl)ethyl]-4-dimethylaminopyridinium chloride
  参考文献：
  名称：

  Synthesis and anticancer activity of analogues of phenstatin, with a phenothiazine A-ring, as a new class of microtubule-targeting agents

  摘要：

  A new family of microtubule-targeting agents with a phenothiazine A-ring was synthesized and evaluated for anti-proliferative activity and interaction with tubulin. These new derivatives showed significant activities against cellular proliferation and tubulin polymerization, rather similar to those of phenstatin. Phenothiazine derivative 21 proved to be the most potent compound synthesized with GI(50) values ranging from 29 to 93 nM on different cell lines. The same compound showed a better inhibition of COLO 205, A498, and MCF7 cell lines than the parent phenstatin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.135

文献信息

• Synthesis and biological evaluation of a new series of phenothiazine-containing protein farnesyltransferase inhibitors
  作者：Cristina-Maria Abuhaie、Alina Ghinet、Amaury Farce、Joëlle Dubois、Philippe Gautret、Benoît Rigo、Dalila Belei、Elena Bîcu

  DOI：10.1016/j.ejmech.2012.11.008

  日期：2013.1

  Two new families of human farnesyltransferase inhibitors 13a-m and 14a-d, based on a phenothiazine scaffold, were synthesized. Compounds 14a and 14b were the most promising inhibitors of human farnesyltransferase with IC50 values of 0.7 and 0.6 mu M, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and anticancer activity of analogues of phenstatin, with a phenothiazine A-ring, as a new class of microtubule-targeting agents
  作者：Cristina-Maria Abuhaie、Elena Bîcu、Benoît Rigo、Philippe Gautret、Dalila Belei、Amaury Farce、Joëlle Dubois、Alina Ghinet

  DOI：10.1016/j.bmcl.2012.10.135

  日期：2013.1

  A new family of microtubule-targeting agents with a phenothiazine A-ring was synthesized and evaluated for anti-proliferative activity and interaction with tubulin. These new derivatives showed significant activities against cellular proliferation and tubulin polymerization, rather similar to those of phenstatin. Phenothiazine derivative 21 proved to be the most potent compound synthesized with GI(50) values ranging from 29 to 93 nM on different cell lines. The same compound showed a better inhibition of COLO 205, A498, and MCF7 cell lines than the parent phenstatin. (C) 2012 Elsevier Ltd. All rights reserved.