(R)-amino-(1-tert-butoxycarbonyl-piperidin-4-yl)-acetic acid methyl ester | 357413-60-6

• 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)-amino-(1-tert-butoxycarbonyl-piperidin-4-yl)-acetic acid methyl ester
• 英文别名: (R)-tert-Butyl 4-(1-amino-2-methoxy-2-oxoethyl)piperidine-1-carboxylate；tert-butyl 4-[(1R)-1-amino-2-methoxy-2-oxoethyl]piperidine-1-carboxylate
• CAS: 357413-60-6
• 化学式: C₁₃H₂₄N₂O₄
• 分子量: 272.345
• InChiKey: KCWQYYUIIOHOLI-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-amino-(1-tert-butoxycarbonyl-piperidin-4-yl)-acetic acid methyl ester 在 lithium hydroxide 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (R)-(1-tert-butoxycarbonyl-piperidin-4-yl)-(4'-methoxy-biphenyl-4-sulfonylamino)-acetic acid
  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：

  [(9H-fluoren-9-ylmethoxycarbonylamino)]-(1-tert-butoxycarbonyl-piperidin-4-yl)-acetic acid methyl ester 在 palladium on activated charcoal 三甲基硅烷化重氮甲烷 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 反应 24.0h， 生成 (R)-amino-(1-tert-butoxycarbonyl-piperidin-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