[(4'-methoxy-biphenyl-4-sulfonyl)-(2-methoxy-ethyl)-amino]-[1-(2-methoxy-ethoxycarbonyl)-piperidine-4-yl]-acetic acid methyl ester | 357413-58-2

• 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: [(4'-methoxy-biphenyl-4-sulfonyl)-(2-methoxy-ethyl)-amino]-[1-(2-methoxy-ethoxycarbonyl)-piperidine-4-yl]-acetic acid methyl ester
• 英文别名: 2-Methoxyethyl 4-[2-methoxy-1-[2-methoxyethyl-[4-(4-methoxyphenyl)phenyl]sulfonylamino]-2-oxoethyl]piperidine-1-carboxylate
• CAS: 357413-58-2
• 化学式: C₂₈H₃₈N₂O₉S
• 分子量: 578.684
• InChiKey: MZHDODFOTAXJOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(4'-methoxy-biphenyl-4-sulfonyl)-(2-methoxy-ethyl)-amino]-[1-(2-methoxy-ethoxycarbonyl)-piperidine-4-yl]-acetic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 以81%的产率得到4-{Carboxy-[(4'-methoxy-biphenyl-4-sulfonyl)-(2-methoxy-ethyl)-amino]-methyl}-piperidine-1-carboxylic acid 2-methoxy-ethyl ester
  参考文献：
  名称：

  Potent and Selective Carboxylic Acid-Based Inhibitors of Matrix Metalloproteinases

  摘要：

  A novel series of carboxylic acids containing a substituted piperidine were synthesized and tested for inhibition of selected matrix metalloproteinases. Multiple analogues prepared based on this novel design were found to inhibit the target MMPs (MMP-2, -3, -8, -9, and -13) with unprecedented, low nanomolar potency while, at the same time, sparing MMP-1 and MMP-7. Solubility and plasma protein binding of several members of this new series of carboxylic acids were also investigated.

  DOI：

  10.1021/jm015531s
• 作为产物：
  描述：

  2-氨基-2-(1-Boc-4-哌啶基)乙酸甲酯 在 caesium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 [(4'-methoxy-biphenyl-4-sulfonyl)-(2-methoxy-ethyl)-amino]-[1-(2-methoxy-ethoxycarbonyl)-piperidine-4-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Potent and Selective Carboxylic Acid-Based Inhibitors of Matrix Metalloproteinases

  摘要：

  A novel series of carboxylic acids containing a substituted piperidine were synthesized and tested for inhibition of selected matrix metalloproteinases. Multiple analogues prepared based on this novel design were found to inhibit the target MMPs (MMP-2, -3, -8, -9, and -13) with unprecedented, low nanomolar potency while, at the same time, sparing MMP-1 and MMP-7. Solubility and plasma protein binding of several members of this new series of carboxylic acids were also investigated.

  DOI：

  10.1021/jm015531s