ethyl 7-{[({2-[(5-bromo-2-thienyl)carbonyl]hydrazino}carbonothioyl)amino]carbonyl}-2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carboxylate | 1239973-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: ethyl 7-{[({2-[(5-bromo-2-thienyl)carbonyl]hydrazino}carbonothioyl)amino]carbonyl}-2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carboxylate
• 英文别名: Ethyl 7-[[(5-bromothiophene-2-carbonyl)amino]carbamothioylcarbamoyl]-2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carboxylate
• CAS: 1239973-39-7
• 化学式: C₁₆H₁₄BrN₃O₆S₃
• 分子量: 520.406
• InChiKey: VJMXQTRBUZTDKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  204
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  硫氰酸铵 、 5-溴噻吩-2-甲酰肼 、 ethyl 7-(chlorocarbonyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carboxylate 在 polyethylene glycol (PEG)-600 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以75%的产率得到ethyl 7-{[({2-[(5-bromo-2-thienyl)carbonyl]hydrazino}carbonothioyl)amino]carbonyl}-2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carboxylate
  参考文献：
  名称：

  New Hydrazides and Thiosemicarbazides Derived from Ethylenedioxythiophene as Potential Anticonvulsants

  摘要：

  A series of ethyl 7-({2-[(substituted)carbonyl]hydrazino}carbonyl)-2,3-dihydrothieno [3,4-b][1,4]dioxine-5-carboxylates (5-13) and ethyl 7-{[({2-[(substituted)carbonyl]hydra-zino}carbonothioyl)amino]carbonyl}-2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carboxy-lates (15-20) were synthesized in good yield by condensing ethyl-7-(chlorocarbonyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carboxylate (4) with suitable hydrazides. The newly synthesized compounds were characterized using FTIR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analyses. The anticonvulsant activity of all the title compounds was investigated against maximal electroshock-induced seizures (MES) and pentylenetetrazole (PTZ)-induced convulsion models. None of the compounds showed toxicity at the maximum dose of 2000 mg/kg. Almost all the compounds showed protection in flexion and extension stage against induced convulsion. Among them, naphthyloxy-substituted derivatives exhibited very good response against induced seizures. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

  DOI：

  10.1080/10426500903051831