ethyl 2-[3-(4-(tert-butoxycarbonyl)piperazin-1-yl)-4-(methylsulfonylamino)phenyl]propionate | 1354694-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: ethyl 2-[3-(4-(tert-butoxycarbonyl)piperazin-1-yl)-4-(methylsulfonylamino)phenyl]propionate
• CAS: 1354694-65-7
• 化学式: C₂₁H₃₃N₃O₆S
• 分子量: 455.576
• InChiKey: QKIUUILIEABKPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105.25
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-[3-(4-(tert-butoxycarbonyl)piperazin-1-yl)-4-(methylsulfonylamino)phenyl]propionate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 、 二氯甲烷 为溶剂， 反应 4.0h， 以93%的产率得到2-[3-(4-(tert-butoxycarbonyl)piperazin-1-yl)-4-(methylsulfonylamino)phenyl]propionic acid
  参考文献：
  名称：

  N-4-t-Butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamide TRPV1 antagonists: Structure–activity relationships in the A-region

  摘要：

  Structure-activity relationships for the A-region in a series of N-4-t-butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamides as TRPV1 antagonists have been investigated. Among them, the 3-fluoro analogue 54 showed high binding affinity and potent antagonism for both rTRPV1 and hTRPV1 in CHO cells. Its stereospecific activity was demonstrated with marked selectivity for the (S)-configuration (54S versus 54R). A docking study of 54S with our hTRPV1 homology model highlighted crucial hydrogen bonds between the ligand and the receptor contributing to its potency. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.008
• 作为产物：
  描述：

  ethyl 2-(3-(4-(tert-butoxycarbonyl)piperazin-1-yl)-4-nitrophenyl)propionate 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.17h， 生成 ethyl 2-[3-(4-(tert-butoxycarbonyl)piperazin-1-yl)-4-(methylsulfonylamino)phenyl]propionate
  参考文献：
  名称：

  N-4-t-Butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamide TRPV1 antagonists: Structure–activity relationships in the A-region

  摘要：

  Structure-activity relationships for the A-region in a series of N-4-t-butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamides as TRPV1 antagonists have been investigated. Among them, the 3-fluoro analogue 54 showed high binding affinity and potent antagonism for both rTRPV1 and hTRPV1 in CHO cells. Its stereospecific activity was demonstrated with marked selectivity for the (S)-configuration (54S versus 54R). A docking study of 54S with our hTRPV1 homology model highlighted crucial hydrogen bonds between the ligand and the receptor contributing to its potency. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.008