5-(4,5-dibromo-1H-pyrrol-2-yl)-1,3,4-oxadiazole-2-thiol | 1408118-12-6

• 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-(4,5-dibromo-1H-pyrrol-2-yl)-1,3,4-oxadiazole-2-thiol
• 英文别名: 5-(4,5-dibromo-1H-pyrrol-2-yl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 1408118-12-6
• 化学式: C₆H₃Br₂N₃OS
• 分子量: 324.983
• InChiKey: FZBBDCVYOQGMJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  81.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4,5-dibromo-1H-pyrrol-2-yl)-1,3,4-oxadiazole-2-thiol 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以40%的产率得到2-(4,5-dibromo-1H-pyrrol-2-yl)-5-methylsulfanyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and evaluation of novel 1,3,4-oxadiazole derivatives of marine bromopyrrole alkaloids as antimicrobial agent

  摘要：

  In an attempt to identify new potential lead as antimicrobial agent, twenty hybrids of marine bromopyrrole alkaloids with 1,3,4-oxadiazole were designed based on molecular hybridization technique and synthesized. Synthesized molecules were evaluated for their antibacterial, antifungal and antitubercular activities. Hybrids 5d, 5i, 5j and 5k exhibited equivalent antibacterial activity (MIC of 1.56 mu g/mL) compared with standard drug ciprofloxacin against Staphylococcus aureus and Escherichia coli. Equal antifungal activity (MIC of 1.56 mu g/mL) was shown by of hybrids 5j, 5k and 7d compared with standard Amphotericin-B. The inhibition of Mycobacterium tuberculosis at concentrations as low as 1.6 and 1.5 mu g/mL by compounds 5f and 7d respectively indicates that these compounds can act as leads for development of newer anti-TB compounds. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.061
• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 在 溴 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 15.0h， 生成 5-(4,5-dibromo-1H-pyrrol-2-yl)-1,3,4-oxadiazole-2-thiol
  参考文献：
  名称：

  Synthesis and evaluation of novel 1,3,4-oxadiazole derivatives of marine bromopyrrole alkaloids as antimicrobial agent

  摘要：

  In an attempt to identify new potential lead as antimicrobial agent, twenty hybrids of marine bromopyrrole alkaloids with 1,3,4-oxadiazole were designed based on molecular hybridization technique and synthesized. Synthesized molecules were evaluated for their antibacterial, antifungal and antitubercular activities. Hybrids 5d, 5i, 5j and 5k exhibited equivalent antibacterial activity (MIC of 1.56 mu g/mL) compared with standard drug ciprofloxacin against Staphylococcus aureus and Escherichia coli. Equal antifungal activity (MIC of 1.56 mu g/mL) was shown by of hybrids 5j, 5k and 7d compared with standard Amphotericin-B. The inhibition of Mycobacterium tuberculosis at concentrations as low as 1.6 and 1.5 mu g/mL by compounds 5f and 7d respectively indicates that these compounds can act as leads for development of newer anti-TB compounds. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.061

文献信息

• Synthesis and evaluation of novel 1,3,4-oxadiazole derivatives of marine bromopyrrole alkaloids as antimicrobial agent
  作者：Rajesh A. Rane、Shweta D. Gutte、Niteshkumar U. Sahu

  DOI：10.1016/j.bmcl.2012.08.061

  日期：2012.10

  In an attempt to identify new potential lead as antimicrobial agent, twenty hybrids of marine bromopyrrole alkaloids with 1,3,4-oxadiazole were designed based on molecular hybridization technique and synthesized. Synthesized molecules were evaluated for their antibacterial, antifungal and antitubercular activities. Hybrids 5d, 5i, 5j and 5k exhibited equivalent antibacterial activity (MIC of 1.56 mu g/mL) compared with standard drug ciprofloxacin against Staphylococcus aureus and Escherichia coli. Equal antifungal activity (MIC of 1.56 mu g/mL) was shown by of hybrids 5j, 5k and 7d compared with standard Amphotericin-B. The inhibition of Mycobacterium tuberculosis at concentrations as low as 1.6 and 1.5 mu g/mL by compounds 5f and 7d respectively indicates that these compounds can act as leads for development of newer anti-TB compounds. (c) 2012 Elsevier Ltd. All rights reserved.