3-(naphhthalen-1-ylcarbmoyl)benzoic acid | 287483-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphhthalen-1-ylcarbmoyl)benzoic acid
• 英文别名: 3-(Naphthalen-1-ylcarbamoyl)benzoic acid
• CAS: 287483-73-2
• 化学式: C₁₈H₁₃NO₃
• 分子量: 291.306
• InChiKey: IBGIDLMEYRZWOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  iso-phthalic acid monobenzyl ester 在 palladium on activated charcoal 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 17.5h， 生成 3-(naphhthalen-1-ylcarbmoyl)benzoic acid
  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

• 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.