5-((1H-benzo[d]imidazol-1-yl)methyl)-1,3,4-oxadiazole-2-thiol | 332128-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-((1H-benzo[d]imidazol-1-yl)methyl)-1,3,4-oxadiazole-2-thiol
• 英文别名: 5-(1H-benzimidazol-1-ylmethyl)-1,3,4-oxadiazole-2-thiol；5-(benzimidazol-1-ylmethyl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 332128-57-1
• 化学式: C₁₀H₈N₄OS
• mdl: MFCD01818158
• 分子量: 232.266
• InChiKey: XVFMCINOUYEXJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-((1H-benzo[d]imidazol-1-yl)methyl)-1,3,4-oxadiazole-2-thiol 、 4-溴-2-氯乙酰苯胺 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以77%的产率得到2-(5-((1H-benzo[d]imidazol-1-yl)methyl)-1,3,4-oxadiazol-2-ylthio)-N-(4-bromophenyl)acetamide
  参考文献：
  名称：

  Synthesis of benzimidazolyl-1,3,4-oxadiazol-2ylthio-N-phenyl (benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents

  摘要：

  To affiliate multiple bioactivities in a compact heteronuclei, two series of benzimidazole based 1,3,4-oxadiazoles were synthesized and assessed in vitro for their efficacy as antimicrobial agents against eight bacteria (Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhi, Proteus vulgaris, Shigella flexneri), four fungi (Aspergillus niger, Aspergillus fumigants, Aspergillus clavatus, Candida albicans) and Mycobacterium tuberculosis H37Rv and best results were observed amongst the N-benzothiazolylaetamide series. The lipophilicity (LogP) influence on the biological profile (MICs) of the prepared products was also discussed. Upon biological screening, it was observed that the majority of the compounds were found to possess a significant broad spectrum antimicrobial (3.12-25 mu g/mL of MIC) and antitubercular (6.25-25 mu g/mL of MIC) potential. The structural assignments of the new products were done on the basis of IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.033
• 作为产物：
  描述：

  邻苯二胺 在 一水合肼 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.5h， 生成 5-((1H-benzo[d]imidazol-1-yl)methyl)-1,3,4-oxadiazole-2-thiol
  参考文献：
  名称：

  Synthesis of benzimidazolyl-1,3,4-oxadiazol-2ylthio-N-phenyl (benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents

  摘要：

  To affiliate multiple bioactivities in a compact heteronuclei, two series of benzimidazole based 1,3,4-oxadiazoles were synthesized and assessed in vitro for their efficacy as antimicrobial agents against eight bacteria (Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhi, Proteus vulgaris, Shigella flexneri), four fungi (Aspergillus niger, Aspergillus fumigants, Aspergillus clavatus, Candida albicans) and Mycobacterium tuberculosis H37Rv and best results were observed amongst the N-benzothiazolylaetamide series. The lipophilicity (LogP) influence on the biological profile (MICs) of the prepared products was also discussed. Upon biological screening, it was observed that the majority of the compounds were found to possess a significant broad spectrum antimicrobial (3.12-25 mu g/mL of MIC) and antitubercular (6.25-25 mu g/mL of MIC) potential. The structural assignments of the new products were done on the basis of IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.033

文献信息

• Synthesis and Biological Activity Test of Some New Five Membered Heterocycles
  作者：Qingchun Xia、Dongfang Xu、Qizhuang He、Xingyu Li、Dazhi Sun

  DOI：10.1002/cjoc.201190017

  日期：2010.12

  A new series of 1,3,4‐oxadiazoles, 1,2,4‐triazoles, 1,3,4‐thiadiazoles were synthesized using alkylhydrazides as the starting materials, and then 1,2,4‐triazoles were used to synthesize [1,2,4]triazolo[3,4‐b][1,3,4]thiadiazoles. All the compounds were evaluated for in vitro antibacterial activity and antitumor activity.

  以烷基酰肼为原料合成了一系列新的1,3,4-恶二唑，1,2,4-三唑，1,3,4-噻二唑，然后使用1,2,4-三唑合成了[ 1,2,4]三唑[3,4- b ] [1,3,4]噻二唑。评价所有化合物的体外抗菌活性和抗肿瘤活性。