N-丁基-5-硝基-2-(2-丙炔基氧基)苯甲酰胺 | 68505-93-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-丁基-5-硝基-2-(2-丙炔基氧基)苯甲酰胺
• 英文名称: N-Butyl-5-nitro-2-(2-propynyloxy)-benzamide
• 英文别名: N-butyl-2-propargyloxy-5-nitrobenzamide；N-Butyl-5-nitro-2-(2-propynyloxy)benzamide；N-butyl-5-nitro-2-prop-2-ynoxybenzamide
• CAS: 68505-93-1
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: BNNHAQLPTDVJRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-丁基-5-硝基-2-(2-丙炔基氧基)苯甲酰胺 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-(piperidin-1-yl)acetamido)-N-butyl-2-(prop-2-ynyloxy)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
• 作为产物：
  描述：

  2-氯-5-硝基苯甲酸 在 sodium hydride 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.5h， 生成 N-丁基-5-硝基-2-(2-丙炔基氧基)苯甲酰胺
  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 2-Alkoxy-5-nitrobenzamides by Phase-Transfer Catalyzed Nucleophilic Substitution of 2-Chloro-5-nitrobenzamides
  作者：Dino Nisato、Marco Frigerio、Giovanni Boccardi、Giovanni Palmisano

  DOI：10.1055/s-1982-30077

  日期：——
• NISATO, D.;FRIGERIO, M.;BOCCARDI, G.;PALMISANO, G., SYNTHESIS, BRD, 1982, N 12, 1081-1083
  作者：NISATO, D.、FRIGERIO, M.、BOCCARDI, G.、PALMISANO, G.

  DOI：——

  日期：——