tert-butyl [3-({4-[(5S)-2-isopropyl-1,3-dioxo-2,7-diazaspiro[4.5]dec-7-yl]-piperidin-1-yl}carbonyl)-6-methylthieno[2,3-b]pyridin-2-yl]carbamate | 1380610-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: tert-butyl [3-({4-[(5S)-2-isopropyl-1,3-dioxo-2,7-diazaspiro[4.5]dec-7-yl]-piperidin-1-yl}carbonyl)-6-methylthieno[2,3-b]pyridin-2-yl]carbamate
• CAS: 1380610-35-4
• 化学式: C₃₀H₄₁N₅O₅S
• 分子量: 583.752
• InChiKey: LMRXSSRFNGAXJA-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  41.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  112.15
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl [3-({4-[(5S)-2-isopropyl-1,3-dioxo-2,7-diazaspiro[4.5]dec-7-yl]-piperidin-1-yl}carbonyl)-6-methylthieno[2,3-b]pyridin-2-yl]carbamate 在 三氟乙酸 作用下， 反应 1.0h， 以76%的产率得到(5S)-7-{1-[(2-amino-6-methylthieno[2,3-b]pyridin-3-yl)carbonyl]piperidin-4-yl}-2-isopropyl-2,7-diazaspiro[4.5]decane-1,3-dione
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of novel spiro-piperidines as acetyl-CoA carboxylase inhibitors

  摘要：

  Spiro-lactone (S)-1 is a potent acetyl-CoA carboxylase (ACC) inhibitor and was found to be metabolically liable in human hepatic microsomes. To remove one of the risk factors in human study by improving the metabolic stability, we focused on modifying the spiro-lactone ring and the benzothiophene portion of the molecule. Spiro-imide derivative 8c containing a 6-methylthieno[2,3-b]pyridine core exhibited potent ACC inhibitory activity and favorable pharmacokinetic profiles in rats. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.047
• 作为产物：
  描述：

  3-bromo-6-methylthieno[2,3-b]pyridine-2-carboxylic acid 在 正丁基锂 、 叠氮磷酸二苯酯 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 tert-butyl [3-({4-[(5S)-2-isopropyl-1,3-dioxo-2,7-diazaspiro[4.5]dec-7-yl]-piperidin-1-yl}carbonyl)-6-methylthieno[2,3-b]pyridin-2-yl]carbamate
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of novel spiro-piperidines as acetyl-CoA carboxylase inhibitors

  摘要：

  Spiro-lactone (S)-1 is a potent acetyl-CoA carboxylase (ACC) inhibitor and was found to be metabolically liable in human hepatic microsomes. To remove one of the risk factors in human study by improving the metabolic stability, we focused on modifying the spiro-lactone ring and the benzothiophene portion of the molecule. Spiro-imide derivative 8c containing a 6-methylthieno[2,3-b]pyridine core exhibited potent ACC inhibitory activity and favorable pharmacokinetic profiles in rats. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.047