tert-butyl ((4'-(((5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)methyl)-3-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)sulfonyl)-D-valinate | 959975-22-5

• 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
• 英文名称: tert-butyl ((4'-(((5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)methyl)-3-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)sulfonyl)-D-valinate
• CAS: 959975-22-5
• 化学式: C₃₃H₃₆F₃NO₆S
• 分子量: 631.713
• InChiKey: HWWHNEXAQIRELC-SSEXGKCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  98.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((4'-(((5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)methyl)-3-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)sulfonyl)-D-valinate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2R)-3-methyl-2-[[4-[4-[(5-oxo-7,8-dihydro-6H-naphthalen-2-yl)oxymethyl]phenyl]-2-(trifluoromethyl)phenyl]sulfonylamino]butanoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of ((4-keto)-phenoxy)methyl biphenyl-4-sulfonamides: A class of potent aggrecanase-1 inhibitors

  摘要：

  The prevention of aggrecan (a key component of cartilage) cleavage via the inhibition of aggrecanase-1 may provide a unique opportunity to stop the progression of cartilage degradation in osteoarthritis. The evaluation of a series of biphenylsulfonamides resulted in the identification of the ((4-keto)-phenoxy) methyl biphenyl-4-sulfonamides analogs (19-21 and 24) with improved Agg-1 inhibition and MMP-2, MMP-13 activity. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.056
• 作为产物：
  描述：

  tert-butyl ((4'-(bromomethyl)-3-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)sulfonyl)-D-valinate 、 6-羟基-1-四氢萘酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 tert-butyl ((4'-(((5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)methyl)-3-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)sulfonyl)-D-valinate
  参考文献：
  名称：

  Synthesis and biological evaluation of ((4-keto)-phenoxy)methyl biphenyl-4-sulfonamides: A class of potent aggrecanase-1 inhibitors

  摘要：

  The prevention of aggrecan (a key component of cartilage) cleavage via the inhibition of aggrecanase-1 may provide a unique opportunity to stop the progression of cartilage degradation in osteoarthritis. The evaluation of a series of biphenylsulfonamides resulted in the identification of the ((4-keto)-phenoxy) methyl biphenyl-4-sulfonamides analogs (19-21 and 24) with improved Agg-1 inhibition and MMP-2, MMP-13 activity. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.056