N'-furfurylidene-N-methyl-3,4-methylenedioxybenzoylhydrazine | 1189062-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N'-furfurylidene-N-methyl-3,4-methylenedioxybenzoylhydrazine
• 英文别名: LASSBio-1003；N-[(E)-furan-2-ylmethylideneamino]-N-methyl-1,3-benzodioxole-5-carboxamide
• CAS: 1189062-69-8
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: XYSLDNQABSATIS-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基 1,3-苯并二恶唑-5-羧酸酯 在 盐酸 、 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 7.0h， 生成 N'-furfurylidene-N-methyl-3,4-methylenedioxybenzoylhydrazine
  参考文献：
  名称：

  Novel furfurylidene N-acylhydrazones derived from natural safrole: discovery of LASSBio-1215, a new potent antiplatelet prototype

  摘要：

  We describe herein the discovery of (E)-N-methyl-N'-((5-nitrofuran-2-yl) methylene) benzo[d][1,3]dioxole-5-carbohydrazide (9e), named LASSBio-1215, as a novel antiplatelet agent belonging to the N-methyl-N-acylhydrazone class, which exert their antiaggregating actions on human and rabbit platelets induced by different agonists, through cyclooxygenase-1 (COX-1) or thromboxane synthase inhibition. This compound was elected after screening of a series of functionalized furyl N-acylhydrazone derivatives, synthesized from natural safrole 10. In vitro assays showed that compound 9e presents platelet-aggregating activity in rabbit platelet-rich plasma (PRP) induced by arachidonic acid (IC50 = 0.7 mu M) and collagen (IC50 = 4.5 mu M). Moreover, LASSBio-1215 also inhibited almost completely the second wave of adenosine diphosphate-induced platelet aggregation in human PRP, and this effect was correlated with their ability to block the production of pro-aggregating autacoid thromboxane A(2).

  DOI：

  10.3109/14756366.2011.578575

文献信息

• Studies towards the identification of putative bioactive conformation of potent vasodilator arylidene N-acylhydrazone derivatives
  作者：Arthur E. Kümmerle、Juliana M. Raimundo、Carla M. Leal、Givanildo S. da Silva、Tatiane L. Balliano、Mariano A. Pereira、Carlos A. de Simone、Roberto T. Sudo、Gisele Zapata-Sudo、Carlos A.M. Fraga

  DOI：10.1016/j.ejmech.2009.04.044

  日期：2009.10

  In this report we disclose the synthesis, vasodilatory activity, and identification of bioactive conformation of new N-acylhydrazone and N-methyl-N-acylhydrazone derivatives, structurally designed by bioisosteric replacements of previously described cardioactive compounds LASSBio-294 and its N-methyl derivative LASSBio-785. Some of these novel derivatives presented improved vasorelaxant properties, being new cardiovascular drug candidates. (C) 2009 Elsevier Masson SAS. All rights reserved.