3-(1H-indol-3-yl)-N-(3-(4-(2-methoxyphenyl)piperazinyl)propyl)propanamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-(1H-indol-3-yl)-N-(3-(4-(2-methoxyphenyl)piperazinyl)propyl)propanamide
• 英文别名: 3-(1H-indol-3-yl)-N-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]propanamide
• 化学式: C₂₅H₃₂N₄O₂
• 分子量: 420.555
• InChiKey: BBFIPEKVGBSHCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl (3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)carbamate 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-(1H-indol-3-yl)-N-(3-(4-(2-methoxyphenyl)piperazinyl)propyl)propanamide
  参考文献：
  名称：

  Novel naftopidil-related derivatives and their biological effects as alpha1-adrenoceptors antagonists and antiproliferative agents

  摘要：

  Eleven novel naftopidil-related compounds that contain amide and indole groups were designed and synthesized. The biological effects of these compounds on three alpha(1)-adrenoceptor subtypes and cancerous human prostate cell lines (PC-3, DU-145, and LNCaP) were determined. Compounds 2, 3, 5, 11, and 12 exhibited an alpha(1)-adrenoceptor antagonistic activity, whereas compounds 9, 10, and 12 displayed moderate antiproliferative activities. Compound 3 exhibited a significant alpha(1D/1A) blocking activity in isolated rat tissues (97.7- and 64.6-fold selective for alpha(1D) and alpha(1A) compared with alpha(1B)) but not a relevant cytotoxic activity. Compound 12 demonstrated a potent and selective alpha(1D/1A) antagonistic activity (47.9- and 19.1-fold for alpha(1D) and alpha(1A), compared with alpha(1B)) and a potent antiproliferative activity in PC-3 cells (IC50 = 15.70 mu M). Further testing confirmed that compound 12 inhibited the growth of PC-3 cells by inducing apoptosis and GO/G1 cell cycle arrest, which was mediated by alpha(1)-adrenoceptor. Therefore, compound 12 is a potential multipotent agent that can act as an effective alpha(1)-adrenoceptor subtype antagonist for treating benign prostatic hyperplasia and a preventive medication against human prostate cancer. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.005

文献信息

• Novel naftopidil-related derivatives and their biological effects as alpha1-adrenoceptors antagonists and antiproliferative agents
  作者：Junjun Huang、Fei He、Minyi Huang、Xiawen Liu、Yan Xiong、Yajian Huang、Liu Zhu、Ya Yang、Xingjie Xu、Mu Yuan

  DOI：10.1016/j.ejmech.2015.04.005

  日期：2015.5

  Eleven novel naftopidil-related compounds that contain amide and indole groups were designed and synthesized. The biological effects of these compounds on three alpha(1)-adrenoceptor subtypes and cancerous human prostate cell lines (PC-3, DU-145, and LNCaP) were determined. Compounds 2, 3, 5, 11, and 12 exhibited an alpha(1)-adrenoceptor antagonistic activity, whereas compounds 9, 10, and 12 displayed moderate antiproliferative activities. Compound 3 exhibited a significant alpha(1D/1A) blocking activity in isolated rat tissues (97.7- and 64.6-fold selective for alpha(1D) and alpha(1A) compared with alpha(1B)) but not a relevant cytotoxic activity. Compound 12 demonstrated a potent and selective alpha(1D/1A) antagonistic activity (47.9- and 19.1-fold for alpha(1D) and alpha(1A), compared with alpha(1B)) and a potent antiproliferative activity in PC-3 cells (IC50 = 15.70 mu M). Further testing confirmed that compound 12 inhibited the growth of PC-3 cells by inducing apoptosis and GO/G1 cell cycle arrest, which was mediated by alpha(1)-adrenoceptor. Therefore, compound 12 is a potential multipotent agent that can act as an effective alpha(1)-adrenoceptor subtype antagonist for treating benign prostatic hyperplasia and a preventive medication against human prostate cancer. (C) 2015 Elsevier Masson SAS. All rights reserved.