5,7-dichloro-2-hydrazinyl-1,3-benzoxazole | 1267064-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 5,7-dichloro-2-hydrazinyl-1,3-benzoxazole
• 英文别名: 5,7-dichloro-2-hydrazino-1,3-benzoxazole；(5,7-dichloro-1,3-benzoxazol-2-yl)hydrazine
• CAS: 1267064-00-5
• 化学式: C₇H₅Cl₂N₃O
• 分子量: 218.042
• InChiKey: DBFYPNBJOYPFMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-dichloro-2-hydrazinyl-1,3-benzoxazole 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成 6,8-dichloro-2-{[(4-nitrophenyl)amino]methyl}[1,2,4]triazolo[3,4-b][1,3]benzoxazole-3(2H)-thione
  参考文献：
  名称：

  Synthesis, in vitro antioxidant, anthelmintic and molecular docking studies of novel dichloro substituted benzoxazole-triazolo-thione derivatives

  摘要：

  A novel 6,8-dichloro [1,2,4]triazolo [3,4-b] [1,3]benzoxazole-3(2H)-thione 4 and its derivatives 5a and 5b are synthesized from 5,7-dichloro-2-hydrazinyl-1,3-benzoxazole 3, obtained by reaction of hydrazine hydrate with ethyl [(5,7-dichloro-1,3-benzoxazol-2-yl)sulfanyl]acetate 2. The newly synthesized compounds are characterized by analytical (1)H NMR,(13)C NMR, LC-MS mass spectrometry and elemental analysis. All synthesized compounds are screened for in vitro antioxidant and anthelmintic activities. In correlation to anthelmintic activity, compounds are subjected to molecular docking studies for the binding to beta-Tubulin, target protein elite to the parasites.Compounds 3, 4 and Sa exhibited potential radical scavenging capacity with good anthelmintic activity. In molecular docking study also, compounds showed minimum binding energy and have good affinity toward the active pocket thus, they may be considered as good inhibitor of beta-Tubulin. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.017
• 作为产物：
  描述：

  5,7-dichloro-2-(ethylthio)-1,3-benzoxazole 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以70%的产率得到5,7-dichloro-2-hydrazinyl-1,3-benzoxazole
  参考文献：
  名称：

  Synthesis, antimicrobial, analgesic activity, and molecular docking studies of novel 1-(5,7-dichloro-1,3-benzoxazol-2-yl)-3-phenyl-1H-pyrazole-4-carbaldehyde derivatives

  摘要：

  Condensation of 5,7-dichloro-2-hydrazino-1,3-benzoxazole 3 with different aromatic acetophenones in methanol using catalytic amount of glacial acetic acid afforded the corresponding 1-phenylethanone(5,7-dichloro-1,3-benzoxazol-2-yl)hydrazones 5a-e in good yield. The compounds 5a-e, when subjected to Vilsmeier-Haack reaction with POCl3 in DMF yielded (5,7-dichloro-1,3-benzoxazol-2-yl)-3-phenyl-1H-pyrazole-4-carbaldehyde derivatives 6a-e. The structural assignments of the compounds 6a-e are based on their spectral data and elemental analysis. The obtained compounds were tested for antimicrobial and analgesic activities, and subjected to molecular docking studies with respect to antimicrobial activity. The compound 6b showed pronounced antimicrobial and analgesic activity and exhibited an interesting binding profile with very high receptor affinity.

  DOI：

  10.1007/s00044-013-0565-9

文献信息

• New pyrazole derivatives containing 1,2,4-triazoles and benzoxazoles as potent antimicrobial and analgesic agents
  作者：A.M. Vijesh、Arun M. Isloor、Prashanth Shetty、S. Sundershan、Hoong Kun Fun

  DOI：10.1016/j.ejmech.2012.12.057

  日期：2013.4

  their excellent therapeutic properties. Present paper describes about the synthesis of three series of new 1,2,4-triazole and benzoxazole derivatives containing substituted pyrazole moiety (11a–d, 12a–d and 13a–d). The newly synthesized compounds were characterized by spectral studies and also by C, H, N analyses. All the synthesized compounds were screened for their analgesic activity by the tail flick

  唑类化合物以其优异的治疗性能而闻名。本论文描述了含有取代的吡唑部分（11a-d，12a-d和13a-d）的三个系列的新的1,2,4-三唑和苯并恶唑衍生物的合成。通过光谱研究以及C，H，N分析对新合成的化合物进行了表征。通过甩尾法筛选所有合成的化合物的镇痛活性。新衍生物的抗菌活性也通过最小稀释浓度（MIC）通过系列稀释法进行。结果表明，化合物11c 在吡唑部分上具有2，5-二氯噻吩取代基和三唑环的化合物具有显着的止痛和抗菌活性。
• Synthesis, in vitro antioxidant, anthelmintic and molecular docking studies of novel dichloro substituted benzoxazole-triazolo-thione derivatives
  作者：R.V. Satyendra、K.A. Vishnumurthy、H.M. Vagdevi、K.P. Rajesh、H. Manjunatha、A. Shruthi

  DOI：10.1016/j.ejmech.2011.03.017

  日期：2011.7

  A novel 6,8-dichloro [1,2,4]triazolo [3,4-b] [1,3]benzoxazole-3(2H)-thione 4 and its derivatives 5a and 5b are synthesized from 5,7-dichloro-2-hydrazinyl-1,3-benzoxazole 3, obtained by reaction of hydrazine hydrate with ethyl [(5,7-dichloro-1,3-benzoxazol-2-yl)sulfanyl]acetate 2. The newly synthesized compounds are characterized by analytical (1)H NMR,(13)C NMR, LC-MS mass spectrometry and elemental analysis. All synthesized compounds are screened for in vitro antioxidant and anthelmintic activities. In correlation to anthelmintic activity, compounds are subjected to molecular docking studies for the binding to beta-Tubulin, target protein elite to the parasites.Compounds 3, 4 and Sa exhibited potential radical scavenging capacity with good anthelmintic activity. In molecular docking study also, compounds showed minimum binding energy and have good affinity toward the active pocket thus, they may be considered as good inhibitor of beta-Tubulin. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis, antimicrobial, analgesic activity, and molecular docking studies of novel 1-(5,7-dichloro-1,3-benzoxazol-2-yl)-3-phenyl-1H-pyrazole-4-carbaldehyde derivatives
  作者：N. D. Jayanna、H. M. Vagdevi、J. C. Dharshan、R. Raghavendra、Sandeep B. Telkar

  DOI：10.1007/s00044-013-0565-9

  日期：2013.12

  Condensation of 5,7-dichloro-2-hydrazino-1,3-benzoxazole 3 with different aromatic acetophenones in methanol using catalytic amount of glacial acetic acid afforded the corresponding 1-phenylethanone(5,7-dichloro-1,3-benzoxazol-2-yl)hydrazones 5a-e in good yield. The compounds 5a-e, when subjected to Vilsmeier-Haack reaction with POCl3 in DMF yielded (5,7-dichloro-1,3-benzoxazol-2-yl)-3-phenyl-1H-pyrazole-4-carbaldehyde derivatives 6a-e. The structural assignments of the compounds 6a-e are based on their spectral data and elemental analysis. The obtained compounds were tested for antimicrobial and analgesic activities, and subjected to molecular docking studies with respect to antimicrobial activity. The compound 6b showed pronounced antimicrobial and analgesic activity and exhibited an interesting binding profile with very high receptor affinity.