N-((4'-chlorobenzyl)-(3-(2-chlorophenothiazine-10-yl)-propyl)-N,N-dimethyl-ammonium chloride) | 298688-56-9

• 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: N-((4'-chlorobenzyl)-(3-(2-chlorophenothiazine-10-yl)-propyl)-N,N-dimethyl-ammonium chloride)
• 英文别名: 3-(2-Chlorophenothiazin-10-yl)propyl-[(4-chlorophenyl)methyl]-dimethylazanium;chloride
• CAS: 298688-56-9
• 化学式: C₂₄H₂₅Cl₂N₂S*Cl
• 分子量: 479.901
• InChiKey: IVVQIHBAABRMMX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氯丙嗪 、 4-氯氯苄 以 丙酮 为溶剂， 生成 N-((4'-chlorobenzyl)-(3-(2-chlorophenothiazine-10-yl)-propyl)-N,N-dimethyl-ammonium chloride)
  参考文献：
  名称：

  Synthesis and antitubercular activity of quaternized promazine and promethazine derivatives

  摘要：

  Quaternized chlorpromazine, triflupromazine, and promethazine derivatives were synthesized and examined as antitubercular agents against both actively growing and non-replicating Mycohacterium tuberculosis H37Rv. Impressively, several compounds inhibited non-replicating M. tuberculosis at concentrations equal to or double their MICs against the actively growing strain. All active compounds were non-toxic toward Vero cells (IC50 > 128 mu M). N-Allylchlorpromazinium bromide was only weakly antitubercular, but replacing allyl with benzyl or substituted benzyl improved potency. An electron-withdrawing substituent on the phenothiazine ring was also essential. Branching at the carbon chain decreased antitubercular activity. The optimum antitubercular structures possessed N-(4- or 3-chlorobenzyl) substitution on triflupromazine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.091

文献信息

• Synthesis and antitubercular activity of quaternized promazine and promethazine derivatives
  作者：Aaron B. Bate、Jay H. Kalin、Eric M. Fooksman、Erica L. Amorose、Cristofer M. Price、Heather M. Williams、Michael J. Rodig、Miguel O. Mitchell、Sang Hyun Cho、Yuehong Wang、Scott G. Franzblau

  DOI：10.1016/j.bmcl.2006.11.091

  日期：2007.3

  Quaternized chlorpromazine, triflupromazine, and promethazine derivatives were synthesized and examined as antitubercular agents against both actively growing and non-replicating Mycohacterium tuberculosis H37Rv. Impressively, several compounds inhibited non-replicating M. tuberculosis at concentrations equal to or double their MICs against the actively growing strain. All active compounds were non-toxic toward Vero cells (IC50 > 128 mu M). N-Allylchlorpromazinium bromide was only weakly antitubercular, but replacing allyl with benzyl or substituted benzyl improved potency. An electron-withdrawing substituent on the phenothiazine ring was also essential. Branching at the carbon chain decreased antitubercular activity. The optimum antitubercular structures possessed N-(4- or 3-chlorobenzyl) substitution on triflupromazine. (c) 2006 Elsevier Ltd. All rights reserved.