2-cyclohexyloxy-5-nitro-N-butylbenzamide | 96206-50-7

• 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: 2-cyclohexyloxy-5-nitro-N-butylbenzamide
• 英文别名: N-butyl-2-cyclohexyloxy-5-nitro-benzamide；N-butyl-2-cyclohexyloxy-5-nitrobenzamide
• CAS: 96206-50-7
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: DVONMSGWOSRYDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  483.1±35.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  2-cyclohexyloxy-5-nitro-N-butylbenzamide 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 5-(2-bromoacetamido)-N-butyl-2-(cyclohexyloxy)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 2-cyclohexyloxy-5-nitro-N-butylbenzamide
  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 substituted benzamides as anti-inflammatory agents that inhibit preferentially cyclooxygenase 1 but do not cause gastric damage
  作者：G Caliendo

  DOI：10.1016/s0223-5234(01)01251-x

  日期：2001.6

  Parsalmide (5-amino-N-butyl-2-(2-propynyloxy) benzamide) (5a), is a non-steroidal anti-inflammatory drug (NSAID), commercialised in Italy until 1985 with the brand name of Synovial(R), that has been widely used to treat arthritic patient. In addition, it was shown to spare gastric mucosa. Here we have synthesised a series of novel substituted benzamides, related to Parsalmide, and have evaluated their activity in vitro on COX-1 and COX-2 as well as in vivo in the carrageenin-induced rat paw edema, a classical in vivo anti-inflammatory assay. Compounds 5b, 11a and 11b, which showed a favourable profile in vitro and in vivo, were screened in comparison with Parsalmide for gastrointestinal (GI) tolerability in vivo in the rat. Results obtained showed that Parsalmide and compound 11b inhibited both COX-1 and COX-2 in vitro as well as they were active in vivo. Both compounds were devoid of gastric effect at the efficacious dose. In addition, both prevented indomethacin-induced gastric damage. Thus, these compounds may guide the definition of a new leading structure with anti-inflammatory activity that may allow designing new safer NSAIDs. (C) 2001 Editions scientifiques et medicales Elsevier SAS.
• NISATO, D.;SACILOTTO, R.;FRIGERIO, M.;BOVERI, S.;PALMISANO, G.;LESMA, G., ORG. PREP. AND PROCED. INT., 1985, 17, N 1, 75-80
  作者：NISATO, D.、SACILOTTO, R.、FRIGERIO, M.、BOVERI, S.、PALMISANO, G.、LESMA, G.

  DOI：——

  日期：——
• 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.