(R)-(1-tert-butoxycarbonyl-piperidin-4-yl)-(4'-methoxy-biphenyl-4-sulfonylamino)-acetic acid methyl ester | 357413-61-7

• 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)-(1-tert-butoxycarbonyl-piperidin-4-yl)-(4'-methoxy-biphenyl-4-sulfonylamino)-acetic acid methyl ester
• 英文别名: tert-butyl 4-[(1R)-2-methoxy-1-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-2-oxoethyl]piperidine-1-carboxylate
• CAS: 357413-61-7
• 化学式: C₂₆H₃₄N₂O₇S
• 分子量: 518.631
• InChiKey: VDYMRLBQHPQREI-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-(1-tert-butoxycarbonyl-piperidin-4-yl)-(4'-methoxy-biphenyl-4-sulfonylamino)-acetic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以46%的产率得到(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 碳酸氢钠 、 三甲基硅烷化重氮甲烷 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 反应 24.0h， 生成 (R)-(1-tert-butoxycarbonyl-piperidin-4-yl)-(4'-methoxy-biphenyl-4-sulfonylamino)-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

文献信息

• Potent and Selective Carboxylic Acid-Based Inhibitors of Matrix Metalloproteinases
  作者：Stanislaw Pikul、Norman E. Ohler、Greg Ciszewski、Michael C. Laufersweiler、Neil G. Almstead、Biswanath De、Michael G. Natchus、Lily C. Hsieh、Michael J. Janusz、Sean X. Peng、Todd M. Branch、Selane L. King、Yetunde O. Taiwo、Glen E. Mieling

  DOI：10.1021/jm015531s

  日期：2001.8.1

  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.