Methyl 2-{4-[4-(3-ethoxyphenyl)-3-methylphenyl]piperidin-1-ylsulphonyl}acetate | 227305-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: Methyl 2-{4-[4-(3-ethoxyphenyl)-3-methylphenyl]piperidin-1-ylsulphonyl}acetate
• 英文别名: Methyl 2-[4-[4-(3-ethoxyphenyl)-3-methylphenyl]piperidin-1-yl]sulfonylacetate
• CAS: 227305-45-5
• 化学式: C₂₃H₂₉NO₅S
• 分子量: 431.553
• InChiKey: OUNGSSGQZWVYKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2-{4-[4-(3-ethoxyphenyl)-3-methylphenyl]piperidin-1-ylsulphonyl}acetate 、 碘甲烷 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 Methyl 2-{4-[4-(3-ethoxyphenyl)-3-methylphenyl]piperidin-1-ylsulphonyl}-2-methylpropanoate
  参考文献：
  名称：

  A novel series of highly selective inhibitors of MMP-3

  摘要：

  The design and synthesis of a series of highly selective hydroxamate inhibitors of stromelysin-1 (MMP-3) is described. Substitution of a 4-biaryl piperidine sulfonamide core, which binds at the S1' subsite of MMP-3, was optimised to give potent inhibitors of MMP-3, with greater than 300-fold selectivity over MMP-1, MMP-2, MMP-9 and MMP-14. Compounds 26 and 27 were identified as having the best balance of pharmacology and properties required for topical drug delivery. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.042
• 作为产物：
  描述：

  4-[4-(3-Ethoxyphenyl)-3-methylphenyl]piperidine 、 2-(氯磺酰基)乙酸甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl 2-{4-[4-(3-ethoxyphenyl)-3-methylphenyl]piperidin-1-ylsulphonyl}acetate
  参考文献：
  名称：

  A novel series of highly selective inhibitors of MMP-3

  摘要：

  The design and synthesis of a series of highly selective hydroxamate inhibitors of stromelysin-1 (MMP-3) is described. Substitution of a 4-biaryl piperidine sulfonamide core, which binds at the S1' subsite of MMP-3, was optimised to give potent inhibitors of MMP-3, with greater than 300-fold selectivity over MMP-1, MMP-2, MMP-9 and MMP-14. Compounds 26 and 27 were identified as having the best balance of pharmacology and properties required for topical drug delivery. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.042

文献信息

• HYDROXAMIC ACID DERIVATIVES AS MATRIX METALLOPROTEASE (MMP) INHIBITORS
  申请人：Pfizer Limited

  公开号：EP1036062B1

  公开（公告）日：2004-01-02
• US6495568B1
  申请人：——

  公开号：US6495568B1

  公开（公告）日：2002-12-17
• A novel series of highly selective inhibitors of MMP-3
  作者：Gavin A. Whitlock、Kevin N. Dack、Roger P. Dickinson、Mark L. Lewis

  DOI：10.1016/j.bmcl.2007.10.042

  日期：2007.12

  The design and synthesis of a series of highly selective hydroxamate inhibitors of stromelysin-1 (MMP-3) is described. Substitution of a 4-biaryl piperidine sulfonamide core, which binds at the S1' subsite of MMP-3, was optimised to give potent inhibitors of MMP-3, with greater than 300-fold selectivity over MMP-1, MMP-2, MMP-9 and MMP-14. Compounds 26 and 27 were identified as having the best balance of pharmacology and properties required for topical drug delivery. (c) 2007 Elsevier Ltd. All rights reserved.