3-(2-chloro-10H-phenothiazin-10-yl)-N-methyl-N-(4-(3-(piperidin-1-yl)propoxy)benzyl)-propan-1-amine | 1116338-61-4

• 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: 3-(2-chloro-10H-phenothiazin-10-yl)-N-methyl-N-(4-(3-(piperidin-1-yl)propoxy)benzyl)-propan-1-amine
• 英文别名: ST-713；[3-(2-Chloro-phenothiazin-10-yl)-propyl]-methyl-[4-(3-piperidin-1-yl-propoxy)-benzyl]-amine；3-(2-chlorophenothiazin-10-yl)-N-methyl-N-[[4-(3-piperidin-1-ylpropoxy)phenyl]methyl]propan-1-amine
• CAS: 1116338-61-4
• 化学式: C₃₁H₃₈ClN₃OS
• 分子量: 536.181
• InChiKey: UCQNMJXTWOYVNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(3-(piperidin-1-yl)propoxy)benzaldehyde 、 去甲氯丙嗪 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 3-(2-chloro-10H-phenothiazin-10-yl)-N-methyl-N-(4-(3-(piperidin-1-yl)propoxy)benzyl)-propan-1-amine
  参考文献：
  名称：

  Potential utility of histamine H3 receptor antagonist pharmacophore in antipsychotics

  摘要：

  Histamine H-3 receptor (H3R) antagonists have some antipsychotic properties although the clear molecular mechanism is still unknown. As actually the most effective and less side effective antipsychotics are drugs with multiple targets we have designed typical and atypical neuroleptics with an additional histamine H-3 pharmacophore. The 4-(3-piperidinopropoxy) phenyl pharmacophore moiety has been linked to amitriptyline, maprotiline, chlorpromazine, chlorprothixene, fluphenazine, and clozapine. Amide, amine and ester elements have been used generally to maintain or slightly shift af. nity at dopamine D-2- like receptors (D-2 and D-3), to decrease af. nity at histamine H-1 receptors, and to obtain H3R ligands with low nanomolar or subnanomolar af. nity. Change of effects at D-1-like receptors (D-1 and D-5) were heterogeneous. With these newly pro. led compounds different antipsychotic properties might be achieved. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.012

文献信息

• Potential utility of histamine H3 receptor antagonist pharmacophore in antipsychotics
  作者：Y. von Coburg、T. Kottke、L. Weizel、X. Ligneau、H. Stark

  DOI：10.1016/j.bmcl.2008.09.012

  日期：2009.1

  Histamine H-3 receptor (H3R) antagonists have some antipsychotic properties although the clear molecular mechanism is still unknown. As actually the most effective and less side effective antipsychotics are drugs with multiple targets we have designed typical and atypical neuroleptics with an additional histamine H-3 pharmacophore. The 4-(3-piperidinopropoxy) phenyl pharmacophore moiety has been linked to amitriptyline, maprotiline, chlorpromazine, chlorprothixene, fluphenazine, and clozapine. Amide, amine and ester elements have been used generally to maintain or slightly shift af. nity at dopamine D-2- like receptors (D-2 and D-3), to decrease af. nity at histamine H-1 receptors, and to obtain H3R ligands with low nanomolar or subnanomolar af. nity. Change of effects at D-1-like receptors (D-1 and D-5) were heterogeneous. With these newly pro. led compounds different antipsychotic properties might be achieved. (C) 2008 Elsevier Ltd. All rights reserved.