(E)-N'-(benzo[d][1,3]dioxol-5-ylmethylene)thiophene-2-carbohydrazide

• 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: (E)-N'-(benzo[d][1,3]dioxol-5-ylmethylene)thiophene-2-carbohydrazide
• 英文别名: piperonal-[(thiophene-2-carbonyl)-hydrazone]；Piperonal-[(thiophen-2-carbonyl)-hydrazon]；N'-(1,3-benzodioxol-5-ylmethylene)-2-thiophenecarbohydrazide；N-[(E)-1,3-benzodioxol-5-ylmethylideneamino]thiophene-2-carboxamide
• 化学式: C₁₃H₁₀N₂O₃S
• 分子量: 274.3
• InChiKey: ZUPWGVRDMIWQIZ-VGOFMYFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  噻吩-2-羧酸甲酯 在 盐酸 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 4.5h， 生成 (E)-N'-(benzo[d][1,3]dioxol-5-ylmethylene)thiophene-2-carbohydrazide
  参考文献：
  名称：

  Antihypertensive profile of 2-thienyl-3,4-methylenedioxybenzoylhydrazone is mediated by activation of the A2A adenosine receptor

  摘要：

  Several N-acylhydrazone derivatives synthesized from safrole have been found to promote intense vasodilation and antihypertensive activity. The present work describes the synthesis and antihypertensive profile of 2-thienyl-3,4-methylenedioxybenzoylhydrazone (LASSBio-1027), a new analogue of the lead compound 3,4-methylenedioxybenzoyl-2-thienylhydrazone. Thoracic aortas from Wistar-Kyoto (WKY) rats and spontaneously hypertensive rats (SHR) were prepared for isometric tension recording. Noninvasive blood pressure measurements were made during 14 days of intraperitoneal (10 mg/kg) or oral (20 mg/kg) administration of LASSBio-1027. LASSBio-1027 exhibited partially endothelium-dependent vasorelaxant activity, which was attenuated in the presence of L-NAME, glibenclamide, or ZM 241385. LASSBio-1027 exhibited an antihypertensive effect in SHR during 14 days of intraperitoneal or oral administration, but did not induce a hypotensive effect in normotensive WKY rats. LASSBio-1027-induced vascular relaxation of aortas from WKY rats was mediated by the activation of A(2A) adenosine receptors. Docking studies and binding assays suggested that LASSBio-1027 has affinity for A(2A) and A(3) adenosine receptors. This new N-acylhydrazone derivative represents a potential strategy for the treatment of arterial hypertension. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.056

文献信息

• Buu-Hoi et al., Journal of the Chemical Society, 1953, p. 547
  作者：Buu-Hoi et al.

  DOI：——

  日期：——
• Antihypertensive profile of 2-thienyl-3,4-methylenedioxybenzoylhydrazone is mediated by activation of the A2A adenosine receptor
  作者：Carla Moreira Leal、Sharlene Lopes Pereira、Arthur Eugen Kümmerle、Daniella Moreira Leal、Roberta Tesch、Carlos M.R. de Sant’Anna、Carlos Alberto M. Fraga、Eliezer Jesus Barreiro、Roberto Takashi Sudo、Gisele Zapata-Sudo

  DOI：10.1016/j.ejmech.2012.06.056

  日期：2012.9

  Several N-acylhydrazone derivatives synthesized from safrole have been found to promote intense vasodilation and antihypertensive activity. The present work describes the synthesis and antihypertensive profile of 2-thienyl-3,4-methylenedioxybenzoylhydrazone (LASSBio-1027), a new analogue of the lead compound 3,4-methylenedioxybenzoyl-2-thienylhydrazone. Thoracic aortas from Wistar-Kyoto (WKY) rats and spontaneously hypertensive rats (SHR) were prepared for isometric tension recording. Noninvasive blood pressure measurements were made during 14 days of intraperitoneal (10 mg/kg) or oral (20 mg/kg) administration of LASSBio-1027. LASSBio-1027 exhibited partially endothelium-dependent vasorelaxant activity, which was attenuated in the presence of L-NAME, glibenclamide, or ZM 241385. LASSBio-1027 exhibited an antihypertensive effect in SHR during 14 days of intraperitoneal or oral administration, but did not induce a hypotensive effect in normotensive WKY rats. LASSBio-1027-induced vascular relaxation of aortas from WKY rats was mediated by the activation of A(2A) adenosine receptors. Docking studies and binding assays suggested that LASSBio-1027 has affinity for A(2A) and A(3) adenosine receptors. This new N-acylhydrazone derivative represents a potential strategy for the treatment of arterial hypertension. (C) 2012 Elsevier Masson SAS. All rights reserved.