5-(2-(pyrrolidin-1-yl)acetamido)-N-butyl-2-(adamantanyloxy)benzamide | 1395396-78-7

• 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: 5-(2-(pyrrolidin-1-yl)acetamido)-N-butyl-2-(adamantanyloxy)benzamide
• 英文别名: 2-(1-adamantyloxy)-N-butyl-5-[(2-pyrrolidin-1-ylacetyl)amino]benzamide
• CAS: 1395396-78-7
• 化学式: C₂₇H₃₉N₃O₃
• 分子量: 453.625
• InChiKey: CTVGQJICLUMHNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-butyl-2-(adamantan-1-yloxy)-5-nitrobenzamide 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 7.5h， 生成 5-(2-(pyrrolidin-1-yl)acetamido)-N-butyl-2-(adamantanyloxy)benzamide
  参考文献：
  名称：

  Synthesis of benzamide derivatives and their evaluation as antiprion agents

  摘要：

  A new set of 5-(2-(pyrrolidin-1-yl)acetamido)-N-butyl-2-(substituted) benzamide and 5-(2-(piperidin-1-yl)acetamido)-N-butyl-2-(substituted) benzamide derivatives were synthesized in which as structural features the 2-(1-pyrrolidinyl)- or 2-(1-piperidyl) acetylamino group or a diphenylether moiety are associated to a benzamide scaffold. Their binding affinity for human PrPC and inhibition of its conversion into PrPSc were determined in vitro; moreover, the antiprion activity was assayed by inhibition of PrPSc accumulation in scrapie-infected mouse neuroblastoma cells (ScN2a) and scrapie mouse brain (SMB) cells. The results clearly indicate the benzamide derivatives as attractive lead compounds for the development of potential therapeutic agents against prion disease. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.026

文献信息

• Synthesis of benzamide derivatives and their evaluation as antiprion agents
  作者：Ferdinando Fiorino、Martin Eiden、Armin Giese、Beatrice Severino、Antonella Esposito、Martin H. Groschup、Elisa Perissutti、Elisa Magli、Giuseppina Maria Incisivo、Antonio Ciano、Francesco Frecentese、Hans A. Kretzschmar、Jens Wagner、Vincenzo Santagada、Giuseppe Caliendo

  DOI：10.1016/j.bmc.2012.06.026

  日期：2012.8

  A new set of 5-(2-(pyrrolidin-1-yl)acetamido)-N-butyl-2-(substituted) benzamide and 5-(2-(piperidin-1-yl)acetamido)-N-butyl-2-(substituted) benzamide derivatives were synthesized in which as structural features the 2-(1-pyrrolidinyl)- or 2-(1-piperidyl) acetylamino group or a diphenylether moiety are associated to a benzamide scaffold. Their binding affinity for human PrPC and inhibition of its conversion into PrPSc were determined in vitro; moreover, the antiprion activity was assayed by inhibition of PrPSc accumulation in scrapie-infected mouse neuroblastoma cells (ScN2a) and scrapie mouse brain (SMB) cells. The results clearly indicate the benzamide derivatives as attractive lead compounds for the development of potential therapeutic agents against prion disease. (C) 2012 Elsevier Ltd. All rights reserved.