4-[4-(4,5-dihydro-1,2,4-(4H)-5-oxo-oxadiazol-3-ylmethyl)]-N-2,2,2-trichloroethoxycarbonylaniline | 1229613-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[4-(4,5-dihydro-1,2,4-(4H)-5-oxo-oxadiazol-3-ylmethyl)]-N-2,2,2-trichloroethoxycarbonylaniline
• CAS: 1229613-13-1
• 化学式: C₁₂H₁₀Cl₃N₃O₄
• 分子量: 366.588
• InChiKey: VXFYCNPTZBIWKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.22
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[4-(4,5-dihydro-1,2,4-(4H)-5-oxo-oxadiazol-3-ylmethyl)]-N-2,2,2-trichloroethoxycarbonylaniline 、 1-octadecylpiperazine 以 乙腈 为溶剂， 反应 5.0h， 以60%的产率得到1-[4-(4,5-dihydro-1,2,4-(4H)-5-oxo-oxadiazol-3-ylmethyl)phenylaminocarbonyl]-4-octadecylpiperazine
  参考文献：
  名称：

  Design of new potent and selective secretory phospholipase A2 inhibitors. 6-Synthesis, structure–activity relationships and molecular modelling of 1-substituted-4-[4,5-dihydro-1,2,4-(4H)-oxadiazol-5-one-3-yl(methyl)]-functionalized aryl piperazin/one/dione derivatives

  摘要：

  The group IIA human non-pancreatic secretory phospholipase A(2) (hnp-sPLA(2)) is one of the enzymes implied in the inflammatory process. In the course of our work on inhibitors of this enzyme we investigated the influence of rigidity of the piperazine region on the biological activity. Several modifications were explored. Various linkers, such as amide, urea, carbamate, or alkoxyphenyl were inserted between the piperazine and the lipophilic chain. Also, modification of the piperazine core to incorporate carbonyl groups was studied. In an in vitro fluorimetric assay using the human GIIA (HPLA(2)) and porcine pancreatic GIB enzymes, compound 60a (Y = phenoxy, R = C18H37, Z= CH2) had the optimal activity with an IC50 = 30 nM on HPLA(2). By means of molecular modelling we attempted to get informations towards comprehension of differences in activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.049
• 作为产物：
  描述：

  4-(N-hydroxyamidinomethyl)-N-2,2,2-trichloroethoxycarbonylaniline 、 氯甲酸苯酯 在 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 以64%的产率得到4-[4-(4,5-dihydro-1,2,4-(4H)-5-oxo-oxadiazol-3-ylmethyl)]-N-2,2,2-trichloroethoxycarbonylaniline
  参考文献：
  名称：

  Design of new potent and selective secretory phospholipase A2 inhibitors. 6-Synthesis, structure–activity relationships and molecular modelling of 1-substituted-4-[4,5-dihydro-1,2,4-(4H)-oxadiazol-5-one-3-yl(methyl)]-functionalized aryl piperazin/one/dione derivatives

  摘要：

  The group IIA human non-pancreatic secretory phospholipase A(2) (hnp-sPLA(2)) is one of the enzymes implied in the inflammatory process. In the course of our work on inhibitors of this enzyme we investigated the influence of rigidity of the piperazine region on the biological activity. Several modifications were explored. Various linkers, such as amide, urea, carbamate, or alkoxyphenyl were inserted between the piperazine and the lipophilic chain. Also, modification of the piperazine core to incorporate carbonyl groups was studied. In an in vitro fluorimetric assay using the human GIIA (HPLA(2)) and porcine pancreatic GIB enzymes, compound 60a (Y = phenoxy, R = C18H37, Z= CH2) had the optimal activity with an IC50 = 30 nM on HPLA(2). By means of molecular modelling we attempted to get informations towards comprehension of differences in activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.049