N-(naphthalene-1-yl)-3,5-dinitrobenzamide | 36293-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(naphthalene-1-yl)-3,5-dinitrobenzamide
• 英文别名: 3,5-dinitro-benzoic acid-[1]naphthylamide；(3.5-Dinitro-benzoesaeure)-α-naphthylamid；3,5-Dinitro-benzoesaeure-[1]naphthylamid；N-(naphthalen-1-yl)-3,5-dinitrobenzamide；N-naphthalen-1-yl-3,5-dinitrobenzamide
• CAS: 36293-28-4
• 化学式: C₁₇H₁₁N₃O₅
• 分子量: 337.291
• InChiKey: HXNJCSPTZLUSKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,5-二硝基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N-(naphthalene-1-yl)-3,5-dinitrobenzamide
  参考文献：
  名称：

  Development of 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors

  摘要：

  Human 5-lipoxygenase (5-LOX) is a well-validated target for anti-inflammatory therapy. Development of novel 5-LOX inhibitors with higher activities is highly demanded. In previous study, we have built a model for the active conformation of human 5-LOX, and identified naphthalen-1-yl 3,5-dinitrobenzoate (JMC-4) as a 5-LOX inhibitor by virtual screening. In the present work, 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors were developed. Twenty aryl 3,5-dinitrobenzoates, N-aryl 3,5-dinitrobenzamides and analogues were designed and synthesized. Several of them were found with significantly increased activities according to cell-free assay and human whole blood assay. The structure-activity relationship study may provide useful insights for designing effective 5-LOX inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.008

文献信息

• Johnson; Meade, American Chemical Journal, 1906, vol. 36, p. 300
  作者：Johnson、Meade

  DOI：——

  日期：——
• Development of 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors
  作者：Erchang Shang、Ying Liu、Yiran Wu、Wei Zhu、Chong He、Luhua Lai

  DOI：10.1016/j.bmc.2014.03.008

  日期：2014.4

  Human 5-lipoxygenase (5-LOX) is a well-validated target for anti-inflammatory therapy. Development of novel 5-LOX inhibitors with higher activities is highly demanded. In previous study, we have built a model for the active conformation of human 5-LOX, and identified naphthalen-1-yl 3,5-dinitrobenzoate (JMC-4) as a 5-LOX inhibitor by virtual screening. In the present work, 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors were developed. Twenty aryl 3,5-dinitrobenzoates, N-aryl 3,5-dinitrobenzamides and analogues were designed and synthesized. Several of them were found with significantly increased activities according to cell-free assay and human whole blood assay. The structure-activity relationship study may provide useful insights for designing effective 5-LOX inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.