2-(2-oxobenzo[d]thiazol-3(2H)-yl)acetohydrazide | 97420-38-7

• 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: 2-(2-oxobenzo[d]thiazol-3(2H)-yl)acetohydrazide
• 英文别名: 2-(2-oxo-1,3-benzothiazol-3(2H)-yl)acetohydrazide；2-(2-oxo-1,3-benzothiazol-3-yl)acetohydrazide
• CAS: 97420-38-7
• 化学式: C₉H₉N₃O₂S
• 分子量: 223.255
• InChiKey: XGSZDHKEBSXMHV-UHFFFAOYSA-N

物化性质

• 熔点：
  213-214 °C(Solv: acetonitrile (75-05-8))
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-oxobenzo[d]thiazol-3(2H)-yl)acetohydrazide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 N′-(4-phenylthiazol-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-羟基苯并噻唑 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 13.0h， 生成 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

文献信息

• Rad51/BRCA2 disruptors inhibit homologous recombination and synergize with olaparib in pancreatic cancer cells
  作者：Marinella Roberti、Fabrizio Schipani、Greta Bagnolini、Domenico Milano、Elisa Giacomini、Federico Falchi、Andrea Balboni、Marcella Manerba、Fulvia Farabegoli、Francesca De Franco、Janet Robertson、Saverio Minucci、Isabella Pallavicini、Giuseppina Di Stefano、Stefania Girotto、Roberto Pellicciari、Andrea Cavalli

  DOI：10.1016/j.ejmech.2019.01.008

  日期：2019.3

  double-strand break repair. Here, we have computationally designed, synthesized, and tested over 40 novel derivatives. Additionally, we designed and conducted novel biological assays to characterize how they disrupt the Rad51-BRCA2 interaction and inhibit double-strand break repair. These compounds synergized with olaparib to target pancreatic cancer cells with functional BRCA2. This supports the idea that

  OlaPARib是一种PARP抑制剂（PARPi）。对于携带BRCA1或BRCA2突变的患者，奥拉帕尼被批准用于治疗卵巢癌，并在临床试验中被批准用于治疗乳腺癌和胰腺癌。在BRCA2缺陷患者中，PARPi抑制DNA单链断裂修复，而BRCA2突变阻碍双链断裂修复。最近，我们发现了一系列三唑衍生物，它们通过破坏Rad51-BRCA2的相互作用从而模拟双链断裂修复来模拟BRCA2突变。在这里，我们已经通过计算设计，合成和测试了40多种新型衍生物。此外，我们设计并进行了新颖的生物学分析，以表征它们如何破坏Rad51-BRCA2相互作用并抑制双链断裂修复。这些化合物与olaPARib协同作用，靶向具有功能性BRCA2的胰腺癌细胞。这支持了有机小分子可以模仿基因突变以改善精密医学用抗癌药物的观点的观点。此外，可以在其他遗传途径中利用这种范例来发现创新的抗癌靶标和候选药物。
• Synthesis of some new hydrazone derivatives containing benzothiazole moiety
  作者：Ahmet Özdemir、Gülhan Turan-Zitouni、Asim Kaplancikli、Dilek Altintop

  DOI：10.2298/jsc110321171o

  日期：——

  Hydrazones are an important class of compounds found in many syn- thetic products. Due to their importance in synthetic chemistry, the present ar- ticle reports the synthesis of a new series of ten compounds based on the coup- ling of 2-oxo-3(2H)-benzothiazoleacetic acid, hydrazide and 2-thioxo-3(2H)- -benzothiazoleacetic acid, hydrazide with different aldehydes. The structures of the synthesized compounds

  dra是在许多合成产品中发现的一类重要的化合物。由于它们在合成化学中的重要性，本论文报道了基于2-oxo-3（2H）-苯并噻唑乙酸，酰肼和2-thioxo-3（ 2H）-苯并噻唑乙酸，酰肼与不同的醛。合成的化合物的结构通过元素分析，IR，1 H-NMR，13 C-NMR和FAB + -MS光谱数据证实。
• D'Amico, John J.; Bollinger, Frederick G., Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1183 - 1190
  作者：D'Amico, John J.、Bollinger, Frederick G.

  DOI：——

  日期：——
• Weng, Jian-Quan; Huang, Hua; Yu, Zhi-Qin, Asian Journal of Chemistry, 2012, vol. 24, # 2, p. 561 - 564
  作者：Weng, Jian-Quan、Huang, Hua、Yu, Zhi-Qin、Zhang, Hong-Min、Tan, Cheng-Xia、Liu, Xing-Hai

  DOI：——

  日期：——
• Synthesis and anticonvulsant activity of some (2/4-substituted)benzaldehyde (2-oxobenzothiazolin-3-yl)acetohydrazones
  作者：Bilge Çakir、Engin Yildirim、Taner Ercanli、Kevser Erol、M.Fethi Sahin

  DOI：10.1016/s0014-827x(99)00110-x

  日期：1999.11

  Fifteen new (2/4-substituted)benzaldehyde (2-oxobenzothiazolin-3-yl)acetohydrazones were synthesized and their structures were elucidated by NMR and elemental analysis. Their anticonvulsant activity was tested by a pentylenetetrazole induced seizure test. Compounds 4e and 4h were found to be the most promising among the others. (C) 1999 Elsevier Science S.A. All rights reserved.