methyl (5R,7S,8R)-8-(4-((2-methylquinolin-4-yl)methoxy)benzamido)-1-oxaspiro[4.4]nonane-7-carboxylate | 681284-42-4

• 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: methyl (5R,7S,8R)-8-(4-((2-methylquinolin-4-yl)methoxy)benzamido)-1-oxaspiro[4.4]nonane-7-carboxylate
• CAS: 681284-42-4
• 化学式: C₂₈H₃₀N₂O₅
• 分子量: 474.557
• InChiKey: WFXYMQZBRLEHCG-KSCKTEMCSA-N

物化性质

• 沸点：
  681.3±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  86.75
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (5R,7S,8R)-8-(4-((2-methylquinolin-4-yl)methoxy)benzamido)-1-oxaspiro[4.4]nonane-7-carboxylate 在 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  α,β-Cyclic-β-benzamido hydroxamic acids: Novel oxaspiro[4.4]nonane templates for the discovery of potent, selective, orally bioavailable inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  Two novel oxaspiro[4.4] nonane beta-benzamido hydroxamic scaffolds have been synthesized in enantio- and diasteriomerically pure form. These templates proved to be exceptional platforms that have led to the discovery of potent inhibitors of TACE that are active in a cellular assay measuring suppression of LPS-induced TNF-alpha. Furthermore, these inhibitors are selective against related MMPs, demonstrate permeability in a Caco-2 assay, and display good oral bioavailability. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.030
• 作为产物：
  描述：

  4-[(2-甲基-4-喹啉基)甲氧基]-苯甲酸 、 甲基(5R,7S,8R)-8-氨基-1-氧杂螺[4.4]壬烷-7-羧酸酯 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到methyl (5R,7S,8R)-8-(4-((2-methylquinolin-4-yl)methoxy)benzamido)-1-oxaspiro[4.4]nonane-7-carboxylate
  参考文献：
  名称：

  α,β-Cyclic-β-benzamido hydroxamic acids: Novel oxaspiro[4.4]nonane templates for the discovery of potent, selective, orally bioavailable inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  Two novel oxaspiro[4.4] nonane beta-benzamido hydroxamic scaffolds have been synthesized in enantio- and diasteriomerically pure form. These templates proved to be exceptional platforms that have led to the discovery of potent inhibitors of TACE that are active in a cellular assay measuring suppression of LPS-induced TNF-alpha. Furthermore, these inhibitors are selective against related MMPs, demonstrate permeability in a Caco-2 assay, and display good oral bioavailability. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.030