N-(6-iodo-benzothiazol-2-yl)-2-[(5-(2-oxo-2H-chromen-3-yl)-[1,3,4]oxadiazol-2-yl)sulfanyl]-acetamide | 1372894-77-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(6-iodo-benzothiazol-2-yl)-2-[(5-(2-oxo-2H-chromen-3-yl)-[1,3,4]oxadiazol-2-yl)sulfanyl]-acetamide
• 英文别名: N-(6-iodo-1,3-benzothiazol-2-yl)-2-[[5-(2-oxochromen-3-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide
• CAS: 1372894-77-3
• 化学式: C₂₀H₁₁IN₄O₄S₂
• 分子量: 562.368
• InChiKey: GZGDZJMUSUMXAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-氧酰肼-2H-1-苯并吡喃-3-羧酸 在 二硫化碳 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 N-(6-iodo-benzothiazol-2-yl)-2-[(5-(2-oxo-2H-chromen-3-yl)-[1,3,4]oxadiazol-2-yl)sulfanyl]-acetamide
  参考文献：
  名称：

  Synthesis of coumarin-based 1,3,4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides as antimicrobial and antituberculosis agents

  摘要：

  In an attempt to find new agents to fight against microbial infections, a series of coumarin-based 1,3,4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides was synthesized starting from coumarin-3-carboxylic acid ethyl ester obtained through Knoevenagel and Pinner reaction. In vitro antimicrobial activity against several bacteria (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, S. flexneri), fungi (A. niger, A. fumigatus, A. clavatus, C. albicans) and antimycobacterial activity against Mycobacterium tuberculosis H37Rv strain was assessed. This study shows to what extent the presence of various electron withdrawing/donating substituents on the phenyl or benzothiazole ring affects the activity profiles of the newer molecules. The relationship between activity profiles (MICs, 3.12-25 mu g/mL) and the lipophilic character (LogP) of the prepared products is also discussed and the MIC values of the active conjugates seem to correlate to some extent with the lipophilicity profiles. Two (5e and 6c) of the final analogues displayed promising antimycobacterial activity at 12.5 mu g/mL of MIC, half fold potent to the standard drug pyrazinamide (6.25 mu g/mL). Compounds were characterized by IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis.

  DOI：

  10.1007/s00044-012-0026-x

文献信息

• Synthesis of coumarin-based 1,3,4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides as antimicrobial and antituberculosis agents
  作者：Rahul V. Patel、Premlata Kumari、Dhanji P. Rajani、Kishor H. Chikhalia

  DOI：10.1007/s00044-012-0026-x

  日期：2013.1

  In an attempt to find new agents to fight against microbial infections, a series of coumarin-based 1,3,4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides was synthesized starting from coumarin-3-carboxylic acid ethyl ester obtained through Knoevenagel and Pinner reaction. In vitro antimicrobial activity against several bacteria (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, S. flexneri), fungi (A. niger, A. fumigatus, A. clavatus, C. albicans) and antimycobacterial activity against Mycobacterium tuberculosis H37Rv strain was assessed. This study shows to what extent the presence of various electron withdrawing/donating substituents on the phenyl or benzothiazole ring affects the activity profiles of the newer molecules. The relationship between activity profiles (MICs, 3.12-25 mu g/mL) and the lipophilic character (LogP) of the prepared products is also discussed and the MIC values of the active conjugates seem to correlate to some extent with the lipophilicity profiles. Two (5e and 6c) of the final analogues displayed promising antimycobacterial activity at 12.5 mu g/mL of MIC, half fold potent to the standard drug pyrazinamide (6.25 mu g/mL). Compounds were characterized by IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis.