(4R,5R)-2,2-dimethyl-5-[(2R)-2-phenylpyrrolidine-1-carbonyl]-N-(2-thiophen-2-ylethyl)-1,3-dioxolane-4-carboxamide | 871719-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4R,5R)-2,2-dimethyl-5-[(2R)-2-phenylpyrrolidine-1-carbonyl]-N-(2-thiophen-2-ylethyl)-1,3-dioxolane-4-carboxamide
• CAS: 871719-77-6
• 化学式: C₂₃H₂₈N₂O₄S
• 分子量: 428.552
• InChiKey: IFKCJHDQQQWJIK-VAMGGRTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  96.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2,2-dimethyl-5-[(2R)-2-phenylpyrrolidine-1-carbonyl]-N-(2-thiophen-2-ylethyl)-1,3-dioxolane-4-carboxamide 在 水 、 三氟乙酸 作用下， 生成 (2R,3R)-2,3-dihydroxy-4-oxo-4-((R)-2-phenylpyrrolidin-1-yl)-N-(2-(thiophen-2-yl)ethyl)butanamide
  参考文献：
  名称：

  The discovery of novel tartrate-based TNF-α converting enzyme (TACE) inhibitors

  摘要：

  A novel series of TNF-alpha convertase (TACE) inhibitors which are non-hydroxamate have been discovered. These compounds are bis-amides of L-tartaric acid (tartrate) and coordinate to the active site zinc in a tridentate manner. They are selective for TACE over other MMP's. We report the first X-ray crystal structure for a tartrate-based TACE inhibitor. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.004
• 作为产物：
  描述：

  2-苯基吡咯烷 、 (4R,5R)-2,2-dimethyl-5-(2-thiophen-2-ylethylcarbamoyl)-1,3-dioxolane-4-carboxylic acid 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 生成 (4R,5R)-2,2-dimethyl-5-[(2R)-2-phenylpyrrolidine-1-carbonyl]-N-(2-thiophen-2-ylethyl)-1,3-dioxolane-4-carboxamide 、 (4R,5R)-2,2-dimethyl-5-[(2S)-2-phenylpyrrolidine-1-carbonyl]-N-(2-thiophen-2-ylethyl)-1,3-dioxolane-4-carboxamide
  参考文献：
  名称：

  The discovery of novel tartrate-based TNF-α converting enzyme (TACE) inhibitors

  摘要：

  A novel series of TNF-alpha convertase (TACE) inhibitors which are non-hydroxamate have been discovered. These compounds are bis-amides of L-tartaric acid (tartrate) and coordinate to the active site zinc in a tridentate manner. They are selective for TACE over other MMP's. We report the first X-ray crystal structure for a tartrate-based TACE inhibitor. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.004

文献信息

• Compounds for the treatment of inflammatory disorders
  申请人：Siddiqui Arshad M.

  公开号：US20060178366A1

  公开（公告）日：2006-08-10

  This invention relates to compounds of the Formula (I): or a pharmaceutically acceptable salt, solvate or isomer thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, aggrecanase, ADMP, LpxC, ADAMs, TACE, TNF-α or combinations thereof.

  本发明涉及式（I）的化合物：或其药学上可接受的盐、溶剂或异构体，可用于治疗由MMPs、aggrecanase、ADMP、LpxC、ADAMs、TACE、TNF-α或其组合介导的疾病或病况。
• Compounds for the treatment of inflammatory disorders and microbial diseases
  申请人：Siddiqui Arshad M.

  公开号：US20070167426A1

  公开（公告）日：2007-07-19

  This invention relates to compounds of the Formula (I): or a pharmaceutically acceptable salt, solvate or isomer thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, aggrecanase, ADMP, LpxC, ADAMs, TACE, TNF-α or combinations thereof.

  本发明涉及式(I)的化合物：或其药学上可接受的盐、溶剂或异构体，可用于治疗由MMPs、aggrecanase、ADMP、LpxC、ADAMs、TACE、TNF-α或其组合介导的疾病或病况。
• COMPOUNDS FOR THE TREATMENT OF INFLAMMATORY DISORDERS
  申请人：Guo Zhuyan

  公开号：US20100145048A1

  公开（公告）日：2010-06-10

  This invention relates to compounds of the Formula (I): or a pharmaceutically acceptable salt, solvate or isomer thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, ADAMs, TACE, TNF-α or combinations thereof.

  本发明涉及公式(I)的化合物：或其药学上可接受的盐、溶剂化合物或异构体，可用于治疗由MMPs、ADAMs、TACE、TNF-α或其组合介导的疾病或病症。
• US7638513B2
  申请人：——

  公开号：US7638513B2

  公开（公告）日：2009-12-29
• US7652020B2
  申请人：——

  公开号：US7652020B2

  公开（公告）日：2010-01-26