tert-butyl N-[(2S)-1-(5-fluorospiro[3H-1-benzofuran-2,4'-piperidine]-1'-yl)-3-[(2-oxo-1H-quinolin-8-yl)oxy]propan-2-yl]carbamate | 1528746-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl N-[(2S)-1-(5-fluorospiro[3H-1-benzofuran-2,4'-piperidine]-1'-yl)-3-[(2-oxo-1H-quinolin-8-yl)oxy]propan-2-yl]carbamate
• CAS: 1528746-92-0
• 化学式: C₂₉H₃₄FN₃O₅
• 分子量: 523.604
• InChiKey: QRZNHFFRECLPLP-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-(5-fluorospiro[3H-1-benzofuran-2,4'-piperidine]-1'-yl)-3-[(2-oxo-1H-quinolin-8-yl)oxy]propan-2-yl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 8-{[(2S)-2-amino-3-(5-fluoro-1'H,3H-spiro[1-benzofuran-2,4'-piperidin]-1'-yl)propyl]oxy}quinolin-2(1H)-one
  参考文献：
  名称：

  Structure activity relationships of fused bicyclic and urea derivatives of spirocyclic compounds as potent CCR1 antagonists

  摘要：

  A series of fused bicyclic and urea derivatives of spirocyclic compounds were designed, synthesised and evaluated in vitro as potent CCR1 antagonists. In particular, 4 (7 nM), 44 (1.3 nM), 48 (0.89 nM) and 50 (0.63 nM) were the most potent hCCR1 antagonists in this series of compounds. Moreover, some of these substances demonstrated good rodent cross-over, especially 46 which exhibited very high rat CCR1 binding affinity with an IC50 value of 16 nM. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.062
• 作为产物：
  描述：

  (R)-N-叔丁氧羰基-3-碘代丙氨酸甲酯 在 锂硼氢 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 132.0h， 生成 tert-butyl N-[(2S)-1-(5-fluorospiro[3H-1-benzofuran-2,4'-piperidine]-1'-yl)-3-[(2-oxo-1H-quinolin-8-yl)oxy]propan-2-yl]carbamate
  参考文献：
  名称：

  Structure activity relationships of fused bicyclic and urea derivatives of spirocyclic compounds as potent CCR1 antagonists

  摘要：

  A series of fused bicyclic and urea derivatives of spirocyclic compounds were designed, synthesised and evaluated in vitro as potent CCR1 antagonists. In particular, 4 (7 nM), 44 (1.3 nM), 48 (0.89 nM) and 50 (0.63 nM) were the most potent hCCR1 antagonists in this series of compounds. Moreover, some of these substances demonstrated good rodent cross-over, especially 46 which exhibited very high rat CCR1 binding affinity with an IC50 value of 16 nM. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.062

文献信息

• Structure activity relationships of fused bicyclic and urea derivatives of spirocyclic compounds as potent CCR1 antagonists
  作者：Nafizal Hossain、Marguérite Mensonides-Harsema、Martin E. Cooper、Tomas Eriksson、Svetlana Ivanova、Lena Bergström

  DOI：10.1016/j.bmcl.2013.11.062

  日期：2014.1

  A series of fused bicyclic and urea derivatives of spirocyclic compounds were designed, synthesised and evaluated in vitro as potent CCR1 antagonists. In particular, 4 (7 nM), 44 (1.3 nM), 48 (0.89 nM) and 50 (0.63 nM) were the most potent hCCR1 antagonists in this series of compounds. Moreover, some of these substances demonstrated good rodent cross-over, especially 46 which exhibited very high rat CCR1 binding affinity with an IC50 value of 16 nM. (C) 2013 Elsevier Ltd. All rights reserved.