tert-butyl (2S)-2-[[7-(methanesulfonamido)dibenzothiophen-2-yl]sulfonylamino]-3-methylbutanoate | 1187178-71-7

• 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 (2S)-2-[[7-(methanesulfonamido)dibenzothiophen-2-yl]sulfonylamino]-3-methylbutanoate
• CAS: 1187178-71-7
• 化学式: C₂₂H₂₈N₂O₆S₃
• 分子量: 512.672
• InChiKey: YIBKNWMAEDAXOQ-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[[7-(methanesulfonamido)dibenzothiophen-2-yl]sulfonylamino]-3-methylbutanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-3-methyl-2-(7-(methylsulfonamido)dibenzo[b,d]thiophene-2-sulfonamido)butanoic acid
  参考文献：
  名称：

  Identification of an Orally Efficacious Matrix Metalloprotease 12 Inhibitor for Potential Treatment of Asthma

  摘要：

  MMP-12 plays a significant role in airway inflammation and remodeling. Increased expression and production of MMP-12 have been observed in the lungs of asthmatic patients. Compound 27 was identified as a potent and selective MMP-12 inhibitor possessing good physicochemical properties. In pharmacological studies, the compound was orally efficacious in an MMP-12 induced ear-swelling inflammation model in the mouse with a good dose response. This compound also exhibited oral efficacy in a naturally Ascaris-sensitized sheep asthma model showing significant inhibition of the late phase response to allergen challenge. This compound has been considered for further development as a treatment therapy for asthma.

  DOI：

  10.1021/jm900809r
• 作为产物：
  描述：

  tert-butyl (2S)-2-[(7-aminodibenzothiophen-2-yl)sulfonylamino]-3-methylbutanoate 、 甲基磺酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl (2S)-2-[[7-(methanesulfonamido)dibenzothiophen-2-yl]sulfonylamino]-3-methylbutanoate
  参考文献：
  名称：

  Identification of an Orally Efficacious Matrix Metalloprotease 12 Inhibitor for Potential Treatment of Asthma

  摘要：

  MMP-12 plays a significant role in airway inflammation and remodeling. Increased expression and production of MMP-12 have been observed in the lungs of asthmatic patients. Compound 27 was identified as a potent and selective MMP-12 inhibitor possessing good physicochemical properties. In pharmacological studies, the compound was orally efficacious in an MMP-12 induced ear-swelling inflammation model in the mouse with a good dose response. This compound also exhibited oral efficacy in a naturally Ascaris-sensitized sheep asthma model showing significant inhibition of the late phase response to allergen challenge. This compound has been considered for further development as a treatment therapy for asthma.

  DOI：

  10.1021/jm900809r

文献信息

• Identification of an Orally Efficacious Matrix Metalloprotease 12 Inhibitor for Potential Treatment of Asthma
  作者：Wei Li、Jianchang Li、Yuchuan Wu、Fabio Rancati、Stefania Vallese、Luca Raveglia、Junjun Wu、Rajeev Hotchandani、Nathan Fuller、Kristina Cunningham、Paul Morgan、Susan Fish、Rustem Krykbaev、Xin Xu、Steve Tam、Samuel J. Goldman、William Abraham、Cara Williams、Joseph Sypek、Tarek S. Mansour

  DOI：10.1021/jm900809r

  日期：2009.9.10

  MMP-12 plays a significant role in airway inflammation and remodeling. Increased expression and production of MMP-12 have been observed in the lungs of asthmatic patients. Compound 27 was identified as a potent and selective MMP-12 inhibitor possessing good physicochemical properties. In pharmacological studies, the compound was orally efficacious in an MMP-12 induced ear-swelling inflammation model in the mouse with a good dose response. This compound also exhibited oral efficacy in a naturally Ascaris-sensitized sheep asthma model showing significant inhibition of the late phase response to allergen challenge. This compound has been considered for further development as a treatment therapy for asthma.