1-acetyl-N-(3-(4-(benzyl(ethyl)carbamoyl)piperidin-1-yl)propyl)-N-(3-chlorophenyl)piperidine-4-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-acetyl-N-(3-(4-(benzyl(ethyl)carbamoyl)piperidin-1-yl)propyl)-N-(3-chlorophenyl)piperidine-4-carboxamide
• 英文别名: 1-[3-(N-(1-acetylpiperidine-4-carbonyl)-3-chloro-anilino)propyl]-N-benzyl-N-ethyl-piperidine-4-carboxamide；1-[3-(N-(1-acetylpiperidine-4-carbonyl)-3-chloroanilino)propyl]-N-benzyl-N-ethylpiperidine-4-carboxamide
• 化学式: C₃₂H₄₃ClN₄O₃
• 分子量: 567.171
• InChiKey: HDYHDOVZUHZOKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-乙基苄胺 在 盐酸 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 68.0h， 生成 1-acetyl-N-(3-(4-(benzyl(ethyl)carbamoyl)piperidin-1-yl)propyl)-N-(3-chlorophenyl)piperidine-4-carboxamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel piperidine-4-carboxamide derivatives as potent CCR5 inhibitors

  摘要：

  Based on a putative 'Y shape' pharmacophore model of CCR5 inhibitors, a series of novel piperidine-4-carboxamide derivatives were designed and synthesized using a group-reverse strategy. Among synthesized target compounds, 16g (IC50 = 25.73 nM) and 16i (IC50 = 25.53 nM) showed equivalent inhibitory activity against CCR5 to that of the positive control maraviroc (IC50 = 25.43 nM) in calcium mobilization assay. Selected compounds were further tested for their antiviral activity in HIV-1 single cycle assay. Two compounds, 16g and 16i, displayed antiviral activity with IC50 values of 73.01 nM and 94.10 nM, respectively. Additionally, the pharmacokinetic properties and inhibitory potency against hERG of 16g were evaluated, providing a foundation for ongoing optimization. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.013

文献信息

• Design, synthesis, and biological evaluation of novel piperidine-4-carboxamide derivatives as potent CCR5 inhibitors
  作者：Suwen Hu、Quan Gu、Zhilong Wang、Zhiyong Weng、Yunrui Cai、Xiaowu Dong、Yongzhou Hu、Tao Liu、Xin Xie

  DOI：10.1016/j.ejmech.2013.11.013

  日期：2014.1

  Based on a putative 'Y shape' pharmacophore model of CCR5 inhibitors, a series of novel piperidine-4-carboxamide derivatives were designed and synthesized using a group-reverse strategy. Among synthesized target compounds, 16g (IC50 = 25.73 nM) and 16i (IC50 = 25.53 nM) showed equivalent inhibitory activity against CCR5 to that of the positive control maraviroc (IC50 = 25.43 nM) in calcium mobilization assay. Selected compounds were further tested for their antiviral activity in HIV-1 single cycle assay. Two compounds, 16g and 16i, displayed antiviral activity with IC50 values of 73.01 nM and 94.10 nM, respectively. Additionally, the pharmacokinetic properties and inhibitory potency against hERG of 16g were evaluated, providing a foundation for ongoing optimization. (C) 2013 Elsevier Masson SAS. All rights reserved.