Benzoic acid, 4-[(benzo[1,3]dioxol-5-ylmethylene)amino]-, ethyl ester | 64436-32-4

• 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: Benzoic acid, 4-[(benzo[1,3]dioxol-5-ylmethylene)amino]-, ethyl ester
• 英文别名: ethyl 4-(1,3-benzodioxol-5-ylmethylideneamino)benzoate
• CAS: 64436-32-4
• 化学式: C₁₇H₁₅NO₄
• mdl: MFCD00088898
• 分子量: 297.31
• InChiKey: ZFAGEEKCOVAUTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  109 °C
• 沸点：
  456.1±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzoic acid, 4-[(benzo[1,3]dioxol-5-ylmethylene)amino]-, ethyl ester 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以1.8 g的产率得到ethyl 4-{[(2H-1,3-benzodioxole-5-yl)methyl]amino}benzoate
  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：

  胡椒醛 、 苯佐卡因 以 乙醇 为溶剂， 生成 Benzoic acid, 4-[(benzo[1,3]dioxol-5-ylmethylene)amino]-, ethyl ester
  参考文献：
  名称：

  Synthesis of novel β-amino ketones containing a p-aminobenzoic acid moiety and evaluation of their antidiabetic activities

  摘要：

  报道了使用改进的Mannich反应方案合成了包含对氨基苯甲酸部分的两种系列的β-氨基酮（TM-1和TM-2）。总共23个新目标化合物的分子结构通过1H NMR、13C NMR、ESI-MS和HR-MS进行了表征。随后，它们在体外进行了抗糖尿病活性筛选。化合物1e的α-葡萄糖苷酶抑制（α-GI）活性达到了显著的66.50%水平。六个化合物的过氧化物酶体增殖物激活受体（PPAR）相对激活活性均超过80%，其中特别是2i显示了前所未有的高PPAR值130.91%。建立了这些化合物的结构-活性关系。2i也正在进行更深入的研究。

  DOI：

  10.1007/s11426-012-4816-2

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]芳基)甲基)氨基)苯甲酸及其相应的药学可接受盐和酯类的组合物。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。