5-bromo-2-(thietan-3-yl)-2,4-dihydro-3H-1,2,4-triazole-3-one

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-bromo-2-(thietan-3-yl)-2,4-dihydro-3H-1,2,4-triazole-3-one
• 英文别名: 5-bromo-2,4-dihydro-2-(thietan-3-yl)-1,2,4-triazol-3-one；5-Bromo-2-(thietan-3-yl)-1,2,4-triazol-3-one；5-bromo-2-(thietan-3-yl)-4H-1,2,4-triazol-3-one
• 化学式: C₅H₆BrN₃OS
• 分子量: 236.092
• InChiKey: SYVNPILLHOZREP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(thietan-3-yl)-2,4-dihydro-3H-1,2,4-triazole-3-one 、 1-碘己烷 在 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以65%的产率得到5-bromo-4-n-hexyl-2,4-dihydro-2-(thietan-3-yl)-1,2,4-triazol-3-one
  参考文献：
  名称：

  Synthesis and Antidepressant Activity of 4-Alkyl-5-Bromo-2,4-Dihydro-2-(Thietan-3-YL)-1,2,4-Triazol-3-Ones

  摘要：

  一系列4-烷基-5-溴-2,4-二氢-2-(噻吩-3-基)-1,2,4-三唑-3-酮(IIa-g)通过5-溴-2,4-二氢-2-(噻吩-3-基)-1,2,4-三唑-3-酮(I)与烷基卤化物和二甲基硫酸盐反应合成。合成化合物的结构通过IR、PMR和13C NMR光谱数据得到确认。在非近交系雄性小鼠中使用尾部悬吊和强迫游泳测试研究了合成化合物的抗抑郁活性。化合物I和IIa,c,f,g在一次腹腔注射后在筛选测试中产生了抗抑郁效果，并且在开放场地测试中没有引起镇静和/或精神刺激效果。化合物I产生的抗抑郁效果与氟西汀相当，具有低毒性(IV级毒性)，并且在疗程后在治疗指数和抗抑郁效果的强度方面优于氟西汀。计算的物理化学性质和毒性风险表明所有合成化合物完全符合Lipinski的五规则。最活跃的化合物I的计算药物得分和预测的毒性风险缺失表明它有望创造一种新的具有抗抑郁活性的药物物质。

  DOI：

  10.1007/s11094-021-02394-0
• 作为产物：
  描述：

  3-bromo-5-hydrazino-1-(thietan-3-yl)-1H-1,2,4-triazole 在 水 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 生成 、 、 5-bromo-2-(thietan-3-yl)-2,4-dihydro-3H-1,2,4-triazole-3-one 、
  参考文献：
  名称：

  Investigation of the Solution Phase Chemi-Luminescence of 1,2,4-triazole Derivatives

  摘要：

  We discovered and studied the chemiluminescence occurring during the oxidation of 3-bromo-5-hydrazino-1-(thietan-3-yl)-1H-1,2,4-triazole with superoxide anion. The chemiluminescence wavelength interval was 400-590 nm with the maxima (at 436 and 540 nm) matching the peak fluorescence wavelengths of the reaction products. The possible reaction products were determined by NMR spectroscopy, mass spectrometry, IR and UV spectroscopy. The quantum yield of chemiluminescence was 10(-9) E/mol.

  DOI：

  10.1007/s10593-014-1553-9

文献信息

• Synthesis and Antidepressant Activity of 4-Alkyl-5-Bromo-2,4-Dihydro-2-(Thietan-3-YL)-1,2,4-Triazol-3-Ones
  作者：F. A. Khaliullin、I. L. Nikitina、E. E. Klen、A. F. Miftakhova、N. N. Makarova、R. A. Gabidullin、A. G. Gilmanova

  DOI：10.1007/s11094-021-02394-0

  日期：2021.5

  A series of 4-alkyl-5-bromo-2,4-dihydro-2-(thietan-3-yl)-1,2,4-triazol-3-ones (IIa-g) were synthesized by reacting 5-bromo-2,4-dihydro-2-(thietan-3-yl)-1,2,4-triazol-3-one (I) with alkyl halides and dimethyl sulfate. The structures of the synthesized compounds were confirmed by IR, PMR, and 13C NMR spectroscopic data. The antidepressant activity of the synthesized compounds in non-inbred male mice was investigated using tail-suspension and forced-swim tests. Compounds I and IIa,c,f,g after a single intraperitoneal injection produced antidepressant effects in screening tests and did not cause sedative and/or psychostimulatory effects in the open-field test. Compound I produced an antidepressant effect comparable to that of fluoxetine, had low toxicity (class IV toxicity), and was superior to fluoxetine in therapeutic index and strength of the antidepressant effect after a course of administration. The calculated physicochemical properties and toxic risks showed that all synthesized compounds complied fully with Lipinski’s rule of five. The calculated drug score and absence of predicted toxic risks for the most active compound I suggested that it was promising for creating a new pharmaceutical substance with antidepressant activity.

  一系列4-烷基-5-溴-2,4-二氢-2-(噻吩-3-基)-1,2,4-三唑-3-酮(IIa-g)通过5-溴-2,4-二氢-2-(噻吩-3-基)-1,2,4-三唑-3-酮(I)与烷基卤化物和二甲基硫酸盐反应合成。合成化合物的结构通过IR、PMR和13C NMR光谱数据得到确认。在非近交系雄性小鼠中使用尾部悬吊和强迫游泳测试研究了合成化合物的抗抑郁活性。化合物I和IIa,c,f,g在一次腹腔注射后在筛选测试中产生了抗抑郁效果，并且在开放场地测试中没有引起镇静和/或精神刺激效果。化合物I产生的抗抑郁效果与氟西汀相当，具有低毒性(IV级毒性)，并且在疗程后在治疗指数和抗抑郁效果的强度方面优于氟西汀。计算的物理化学性质和毒性风险表明所有合成化合物完全符合Lipinski的五规则。最活跃的化合物I的计算药物得分和预测的毒性风险缺失表明它有望创造一种新的具有抗抑郁活性的药物物质。
• Investigation of the Solution Phase Chemi-Luminescence of 1,2,4-triazole Derivatives
  作者：R. R. Kayumova、R. R. Muslukhov、M. F. Abdullin、E. E. Klen、F. A. Khaliullin、G. F. Magadeeva、A. V. Mamykin、S. L. Khursan

  DOI：10.1007/s10593-014-1553-9

  日期：2014.10

  We discovered and studied the chemiluminescence occurring during the oxidation of 3-bromo-5-hydrazino-1-(thietan-3-yl)-1H-1,2,4-triazole with superoxide anion. The chemiluminescence wavelength interval was 400-590 nm with the maxima (at 436 and 540 nm) matching the peak fluorescence wavelengths of the reaction products. The possible reaction products were determined by NMR spectroscopy, mass spectrometry, IR and UV spectroscopy. The quantum yield of chemiluminescence was 10(-9) E/mol.