ethyl 4-{[(2H-1,3-benzodioxole-5-yl)methyl]amino}benzoate | 64288-20-6

• 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: ethyl 4-{[(2H-1,3-benzodioxole-5-yl)methyl]amino}benzoate
• 英文别名: 4-piperonylamino-benzoic acid ethyl ester；4-Piperonylamino-benzoesaeure-aethylester；4-(((1,3-benzodioxol-5-yl)methyl)amino)benzoic acid ethyl ester；Ethyl 4-[(1,3-benzodioxol-5-ylmethyl)amino]benzoate；ethyl 4-(1,3-benzodioxol-5-ylmethylamino)benzoate
• CAS: 64288-20-6
• 化学式: C₁₇H₁₇NO₄
• mdl: MFCD00402157
• 分子量: 299.326
• InChiKey: NDVOXAWNJXIRLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-{[(2H-1,3-benzodioxole-5-yl)methyl]amino}benzoate 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 4-{N-[(2H-1,3-benzodioxole-5-yl)methyl][1,1’-biphenyl]-4-sulfonamido}benzoic acid
  参考文献：
  名称：

  Discovery of a benzenesulfonamide-based dual inhibitor of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase that favorably modulates lipid mediator biosynthesis in inflammation

  摘要：

  Leukotrienes (LTs) and prostaglandin (PG)E-2, produced by 5-lipoxygenase (5-LO) and microsomal prostaglandin E-2 synthase-1 (mPGES-1), respectively, are key players in inflammation, and pharmacological suppression of these lipid mediators (LM) represents a strategy to intervene with inflammatory disorders. Previous studies revealed that the benzenesulfonamide scaffold displays efficient 5-LO-inhibitory properties. Here, we structurally optimized benzenesulfonamides which led to an N-phenyl-benzenesulfonamide derivative (compound 47) with potent inhibitory activities (IC50 = 2.3 and 0.4 mu M for isolated 5-LO and 5-LO in intact cells, respectively). Compound 47 prevented the interaction of 5-LO with its activating protein (FLAP) at the nuclear envelope in transfected HEK293 cells as shown by in situ proximity ligation assay. Comprehensive assessment of the LM profile produced by human macrophages revealed the ability of 47 to selectively down-regulate pro-inflammatory LMs (i.e. LTs and PGE(2)) in M1 but to enhance the formation of pro-resolving LMs (i.e. resolvins and maresins) in M2 macrophages. Moreover, 47 strongly inhibited LT formation and cell infiltration in two in vivo models of acute inflammation (i.e., peritonitis and air pouch sterile inflammation in mice). Together, 47 represents a novel LT biosynthesis inhibitor with an attractive pharmacological profile as anti-inflammatory drug that also promotes the biosynthesis of pro-resolving LM. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.031
• 作为产物：
  描述：

  4-piperonylidenamino-benzoic acid ethyl ester 在 三氯化铝 、 kieselguhr 、 乙醇 、 镍 作用下， 生成 ethyl 4-{[(2H-1,3-benzodioxole-5-yl)methyl]amino}benzoate
  参考文献：
  名称：

  DE716668

  摘要：

  公开号：

文献信息

• Hypolipidemic compositions and method employing derivatives of
  申请人：The Dow Chemical Company

  公开号：US04133890A1

  公开（公告）日：1979-01-09

  This invention relates to compositions of 4-(((1,3-benzodioxol-5-yl)methyl)amino)benzoic acid the corresponding pharmaceutically-acceptable salts and the esters thereof. The invention also relates to methods for reducing plasma lipid levels in mammals using the compounds and compositions.

  本发明涉及4-(((1,3-苯并二氧杂环[5,6]）-5-基)甲基)氨基)苯甲酸及其相应的药学上可接受的盐和酯的组合物。本发明还涉及使用这些化合物和组合物降低哺乳动物血浆脂质水平的方法。
• US4133890A
  申请人：——

  公开号：US4133890A

  公开（公告）日：1979-01-09
• US4206145A
  申请人：——

  公开号：US4206145A

  公开（公告）日：1980-06-03
• US4362892A
  申请人：——

  公开号：US4362892A

  公开（公告）日：1982-12-07