N-octadecylaminocarbonylpiperazine | 540527-76-2

• 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: N-octadecylaminocarbonylpiperazine
• 英文别名: N-octadecylpiperazine-1-carboxamide
• CAS: 540527-76-2
• 化学式: C₂₃H₄₇N₃O
• 分子量: 381.646
• InChiKey: ZSYRGCOOJOHMSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  44.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-octadecylaminocarbonylpiperazine 、 4-氯甲基苯甲酰氯 以 二氯甲烷 为溶剂， 以88%的产率得到1-(4-chloromethylbenzoyl)-4-octadecylaminocarbonylpiperazine
  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：

  哌嗪 、 异氰酸十八酯 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到N-octadecylaminocarbonylpiperazine
  参考文献：
  名称：

  Novel inhibitor compounds specific of secreted non-pancreatic human a2phospholipase of group II

  摘要：

  本发明涉及以下式（I）的化合物以及含有该化合物的药物组合物：其中D、Y、A、B、p、q、W和R的含义与规范中定义的含义相同。

  公开号：

  US20050075345A1

文献信息

• Novel inhibitor compounds specific of secreted non-pancreatic human a<sb>2</sb>phospholipase of group II
  申请人：Heymans Francoise

  公开号：US20050075345A1

  公开（公告）日：2005-04-07

  The present invention relates to a compound of the following formula (I) and pharmaceutical compositions containing the compound of formula (I): wherein D, Y, A, B, p, q, W and R have the same meanings as defined in the specification.

  本发明涉及以下式（I）的化合物以及含有该化合物的药物组合物：其中D、Y、A、B、p、q、W和R的含义与规范中定义的含义相同。
• DERIVES DE PIPERAZINE ET LEUR UTILISATION COMME INHIBITEURS DE PHOSPHOLIPASE
  申请人：Yang Ji Chemical Company Ltd.

  公开号：EP1456186A1

  公开（公告）日：2004-09-15
• [EN] NOVEL INHIBITOR COMPOUNDS SPECIFIC OF SECRETED NON-PANCREATIC HUMAN A2 PHOSPHOLIPASE OF GROUP II<br/>[FR] DERIVES DE PIPERAZINE ET LEUR UTILISATION COMME INHIBITEURS DE PHOSPHOLIPASE
  申请人：YANG JI CHEMICAL COMPANY LTD

  公开号：WO2003048139A1

  公开（公告）日：2003-06-12

  Les composés de formule générale (I) dans laquelle D signifie le groupe Z-HET, -HET étant un hétérocycle à 5 chaînons tel que l'oxadiazolone (II) ou la thiazolidine dione (III) de formules (II et III) et -Z étant choisi dans le groupe constitué par -(CR1R2)n- et -(CR1=CR2)n; ou D signifie le groupe Z=HET, -Z- représentant, avec l'hétérocycle, un groupement -Z=HET de formule (IV) ou (V) dans laquelle -Z= représente -CR1=; sont utiles comme inhibiteurs spécifiques de la phospholipase A2 sécrétée non pancréatique humaine (PLA2-snph) de groupe (II), notamment en thérapie de pathologies inflammatoires.
• 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
  作者：Nadia Meddad-Belhabich、Darina Aoun、Atimé Djimdé、Catherine Redeuilh、Georges Dive、France Massicot、François Chau、Françoise Heymans、Aazdine Lamouri

  DOI：10.1016/j.bmc.2010.03.049

  日期：2010.5

  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.