N-[(E)-[(E)-3-(furan-2-yl)prop-2-enylidene]amino]-1,3-benzodioxole-5-carboxamide

• 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-[(E)-[(E)-3-(furan-2-yl)prop-2-enylidene]amino]-1,3-benzodioxole-5-carboxamide
• 化学式: C₁₅H₁₂N₂O₄
• 分子量: 284.271
• InChiKey: RZAKTCOQPMIUHL-JLALNBPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  73.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(E)-[(E)-3-(furan-2-yl)prop-2-enylidene]amino]-1,3-benzodioxole-5-carboxamide 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以92%的产率得到
  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
• 作为产物：
  描述：

  甲基 1,3-苯并二恶唑-5-羧酸酯 在 盐酸 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 N-[(E)-[(E)-3-(furan-2-yl)prop-2-enylidene]amino]-1,3-benzodioxole-5-carboxamide
  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

• Novel furfurylidene <i>N</i>-acylhydrazones derived from natural safrole: discovery of LASSBio-1215, a new potent antiplatelet prototype
  作者：Ana Paula C. Rodrigues、Luciana M.M. Costa、Bruna L.R. Santos、Rodolfo C. Maia、Ana L.P. Miranda、Eliezer J. Barreiro、Carlos A.M. Fraga

  DOI：10.3109/14756366.2011.578575

  日期：2012.2.1

  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).