rac-Ethyl 4-[1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl]benzoate hydrochloride

• 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: rac-Ethyl 4-[1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl]benzoate hydrochloride
• 英文别名: ethyl 4-[1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]benzoate
• 化学式: C₂₅H₄₃N₄O₆Pol
• 分子量: 483.6
• InChiKey: JIFAMUYNXPIZSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  rac-Ethyl 4-[1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl]benzoate hydrochloride 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以67 mg的产率得到ethyl 4-[1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl]benzoate hydrochloride
  参考文献：
  名称：

  Discovery of orally available spirodiketopiperazine-based CCR5 antagonists

  摘要：

  Using the previously reported novel spirodiketopiperazine scaffold, the design and synthesis of orally available CCR5 antagonists was undertaken. Compounds possessing a carboxylic acid function in the appropriate position showed improved oral exposure (AUC) relative to the initial chemical leads without reduction in the antagonist activity. The optimized compound 40 was found to show potent anti-HIV activity. Full details of structure-activity relationship (SAR) study are presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.057
• 作为产物：
  描述：

  对氟苯甲酸乙酯 、 1-butyl-3-(cyclohexylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione hydrochloride 在 potassium carbonate 作用下， 以 乙腈 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 rac-Ethyl 4-[1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl]benzoate hydrochloride
  参考文献：
  名称：

  Discovery of orally available spirodiketopiperazine-based CCR5 antagonists

  摘要：

  Using the previously reported novel spirodiketopiperazine scaffold, the design and synthesis of orally available CCR5 antagonists was undertaken. Compounds possessing a carboxylic acid function in the appropriate position showed improved oral exposure (AUC) relative to the initial chemical leads without reduction in the antagonist activity. The optimized compound 40 was found to show potent anti-HIV activity. Full details of structure-activity relationship (SAR) study are presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.057

文献信息

• Discovery of orally available spirodiketopiperazine-based CCR5 antagonists
  作者：Rena Nishizawa、Toshihiko Nishiyama、Katsuya Hisaichi、Keisuke Hirai、Hiromu Habashita、Yoshikazu Takaoka、Hideaki Tada、Kenji Sagawa、Shiro Shibayama、Kenji Maeda、Hiroaki Mitsuya、Hisao Nakai、Daikichi Fukushima、Masaaki Toda

  DOI：10.1016/j.bmc.2010.05.057

  日期：2010.7

  Using the previously reported novel spirodiketopiperazine scaffold, the design and synthesis of orally available CCR5 antagonists was undertaken. Compounds possessing a carboxylic acid function in the appropriate position showed improved oral exposure (AUC) relative to the initial chemical leads without reduction in the antagonist activity. The optimized compound 40 was found to show potent anti-HIV activity. Full details of structure-activity relationship (SAR) study are presented. (C) 2010 Elsevier Ltd. All rights reserved.