甲基(5R,7S,8R)-8-氨基-1-氧杂螺[4.4]壬烷-7-羧酸酯 | 461665-28-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 甲基(5R,7S,8R)-8-氨基-1-氧杂螺[4.4]壬烷-7-羧酸酯
• 英文名称: (5R,7S,8R)-Methyl 8-amino-1-oxaspiro[4.4]nonane-7-carboxylate
• 英文别名: methyl (5R,7S,8R)-8-amino-1-oxaspiro[4.4]nonane-7-carboxylate
• CAS: 461665-28-1
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: ZYLSZIUORYXFTC-QXFUBDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 以99%的产率得到甲基(5R,7S,8R)-8-氨基-1-氧杂螺[4.4]壬烷-7-羧酸酯
  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

文献信息

• 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)
  作者：Gregory R. Ott、Naoyuki Asakawa、Rui-Qin Liu、Maryanne B. Covington、Mingxin Qian、Krishna Vaddi、Robert C. Newton、James M. Trzaskos、David D. Christ、Laurine Galya、Thomas Scholz、Will Marshall、James J.-W. Duan

  DOI：10.1016/j.bmcl.2008.01.030

  日期：2008.2

  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.