1-[2-(2-oxobenzo[d]thiazol-3(2H)-yl)acetyl]thiosemicarbazide | 1445855-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 1-[2-(2-oxobenzo[d]thiazol-3(2H)-yl)acetyl]thiosemicarbazide
• 英文别名: [[2-(2-Oxo-1,3-benzothiazol-3-yl)acetyl]amino]thiourea
• CAS: 1445855-39-9
• 化学式: C₁₀H₁₀N₄O₂S₂
• 分子量: 282.347
• InChiKey: NQRIUCXEIXDXNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-(2-oxobenzo[d]thiazol-3(2H)-yl)acetyl]thiosemicarbazide 、 2'-溴-4-氯苯乙酮 以 乙醇 为溶剂， 反应 3.0h， 以75%的产率得到N′-(4-(4-chlorophenyl)thiazol-2-yl)-2-(2-oxobenzo[d]thiazol-3(2H)-yl)acetohydrazide
  参考文献：
  名称：

  Synthesis and biological evaluation of some thiazole derivatives as new cholinesterase inhibitors

  摘要：

  In the present study, some thiazole derivatives were synthesized via the ring closure reaction of 1-[2-(2-oxobenzo[d] thiazol-3(2H)-yl)acetyl]thiosemicarbazide with various phenacyl bromides. The chemical structures of the compounds were elucidated by H-1 NMR, C-13 NMR and mass spectral data and elemental analyses. Each derivative was evaluated for its ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) using a modification of Ellman's spectrophotometric method. The compounds were also investigated for their cytotoxic properties using MTT assay. The most potent AChE inhibitor was found as compound 4e (IC50 = 25.5 +/- 2.12 mu g/mL) followed by compounds 4i (IC50 = 38.50 +/- 2.12 mu g/mL), 4c (IC50 = 58.42 +/- 3.14 mu g/mL) and 4g (IC50 = 68 +/- 2.12 mu g/mL) when compared with eserine (IC50 = 0.025 +/- 0.01 mu g/mL). Effective compounds on AChE exhibited weak inhibition on BuChE (IC50 > 80 mu g/mL). MTT assay indicated that the cytotoxic dose (IC50 = 71.67 +/- 7.63 mu g/mL) of compound 4e was higher than its effective dose.

  DOI：

  10.3109/14756366.2011.653355
• 作为产物：
  描述：

  2-(2-氧代-1,3-苯并噻唑-3-基)乙酸乙酯 在 盐酸 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 1-[2-(2-oxobenzo[d]thiazol-3(2H)-yl)acetyl]thiosemicarbazide
  参考文献：
  名称：

  Synthesis and biological evaluation of some thiazole derivatives as new cholinesterase inhibitors

  摘要：

  In the present study, some thiazole derivatives were synthesized via the ring closure reaction of 1-[2-(2-oxobenzo[d] thiazol-3(2H)-yl)acetyl]thiosemicarbazide with various phenacyl bromides. The chemical structures of the compounds were elucidated by H-1 NMR, C-13 NMR and mass spectral data and elemental analyses. Each derivative was evaluated for its ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) using a modification of Ellman's spectrophotometric method. The compounds were also investigated for their cytotoxic properties using MTT assay. The most potent AChE inhibitor was found as compound 4e (IC50 = 25.5 +/- 2.12 mu g/mL) followed by compounds 4i (IC50 = 38.50 +/- 2.12 mu g/mL), 4c (IC50 = 58.42 +/- 3.14 mu g/mL) and 4g (IC50 = 68 +/- 2.12 mu g/mL) when compared with eserine (IC50 = 0.025 +/- 0.01 mu g/mL). Effective compounds on AChE exhibited weak inhibition on BuChE (IC50 > 80 mu g/mL). MTT assay indicated that the cytotoxic dose (IC50 = 71.67 +/- 7.63 mu g/mL) of compound 4e was higher than its effective dose.

  DOI：

  10.3109/14756366.2011.653355