N-((benzyloxycarbamoyl)methyl)-N-(4-methoxybenzenesulfonyl)aminoacetic acid | 914380-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((benzyloxycarbamoyl)methyl)-N-(4-methoxybenzenesulfonyl)aminoacetic acid
• CAS: 914380-15-7
• 化学式: C₁₈H₂₀N₂O₇S
• 分子量: 408.432
• InChiKey: NTDHVIBMPXCNQR-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-((benzyloxycarbamoyl)methyl)-N-(4-methoxybenzenesulfonyl)aminoacetic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、150.0 kPa 条件下， 反应 4.0h， 以90%的产率得到N-[(hydroxycarbamoyl)methyl]-N-(4-methoxyphenylsulfonyl)aminoacetic acid
  参考文献：
  名称：

  Design, synthesis and molecular modeling study of iminodiacetyl monohydroxamic acid derivatives as MMP inhibitors

  摘要：

  As the matrix metalloproteinases (MMPs) can be massively up-regulated in degenerative tissues and degrade the extracellular matrix, these key enzymes are promising targets for the therapy of cancer and other degenerative diseases. Here, we are presenting a series of new non-peptidic hydroxamate-based matrix metalloproteinase inhibitors, MMPIs, incorporating the iminodiacetic (IDA) hydroxamic acid scaffold, as mimics of truncated peptidic MMPIs. A series of alkylaryl and sulfonylaryl groups, on the IDA basic scaffold, was investigated with the aim of improving potency and selectivity against MMPs involved in degenerative diseases. The sulfonamide based IDA derivatives studied (compounds B1-B3) showed to be potent (nM range) against deep S1' pocket MMPs enzymes (i.e., MMP-2). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.011
• 作为产物：
  描述：

  N-(4-methoxybenzenesulfonyl)iminodiacetic acid dipotassium salt 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-((benzyloxycarbamoyl)methyl)-N-(4-methoxybenzenesulfonyl)aminoacetic acid
  参考文献：
  名称：

  Design, synthesis and molecular modeling study of iminodiacetyl monohydroxamic acid derivatives as MMP inhibitors

  摘要：

  As the matrix metalloproteinases (MMPs) can be massively up-regulated in degenerative tissues and degrade the extracellular matrix, these key enzymes are promising targets for the therapy of cancer and other degenerative diseases. Here, we are presenting a series of new non-peptidic hydroxamate-based matrix metalloproteinase inhibitors, MMPIs, incorporating the iminodiacetic (IDA) hydroxamic acid scaffold, as mimics of truncated peptidic MMPIs. A series of alkylaryl and sulfonylaryl groups, on the IDA basic scaffold, was investigated with the aim of improving potency and selectivity against MMPs involved in degenerative diseases. The sulfonamide based IDA derivatives studied (compounds B1-B3) showed to be potent (nM range) against deep S1' pocket MMPs enzymes (i.e., MMP-2). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.011