(R)-tert-butyl 3-methyl-2-(8-nitrodibenzo[b,d]thiophene-3-sulfonamido)butanoate | 1187178-67-1

• 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
• 英文名称: (R)-tert-butyl 3-methyl-2-(8-nitrodibenzo[b,d]thiophene-3-sulfonamido)butanoate
• CAS: 1187178-67-1
• 化学式: C₂₁H₂₄N₂O₆S₂
• 分子量: 464.563
• InChiKey: GRGCTAMUILRTKP-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  115.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 3-methyl-2-(8-nitrodibenzo[b,d]thiophene-3-sulfonamido)butanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 以88%的产率得到(R)-tert-butyl 2-(8-aminodibenzo[b,d]thiophene-3-sulfonamido)-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
• 作为产物：
  描述：

  8-硝基二苯并[b,d]噻吩-3-磺酰氯 、 D-缬氨酸叔丁基盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到(R)-tert-butyl 3-methyl-2-(8-nitrodibenzo[b,d]thiophene-3-sulfonamido)butanoate
  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