2-(1,3-benzodioxol-5-yl)-3-[5-(2-oxo-2H-3-chromenyl)-1,3-oxazol-2-yl]-1,3-thiazolan-4-one | 1295506-34-1

• 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: 2-(1,3-benzodioxol-5-yl)-3-[5-(2-oxo-2H-3-chromenyl)-1,3-oxazol-2-yl]-1,3-thiazolan-4-one
• 英文别名: 2-(1,3-Benzodioxol-5-yl)-3-[5-(2-oxochromen-3-yl)oxazol-2-yl]thiazolidin-4-one；2-(1,3-benzodioxol-5-yl)-3-[5-(2-oxochromen-3-yl)-1,3-oxazol-2-yl]-1,3-thiazolidin-4-one
• CAS: 1295506-34-1
• 化学式: C₂₂H₁₄N₂O₆S
• 分子量: 434.429
• InChiKey: QWVWXOGCFTUIKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-乙酰基香豆素 在 碘 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 2-(1,3-benzodioxol-5-yl)-3-[5-(2-oxo-2H-3-chromenyl)-1,3-oxazol-2-yl]-1,3-thiazolan-4-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of novel 2-(aryl)-3-[5-(2-oxo-2H-3-chromenyl)-1,3-oxazol-2-yl]-1,3-thiazolan-4-ones

  摘要：

  AbstractA series of novel 2‐(aryl)‐3‐[5‐(2‐oxo‐2H‐3‐chromenyl)‐1,3‐oxazol‐2‐yl]‐1,3‐thiazolan‐4‐ones 4a, 4b, 4c, 4e, 4f, 4g, 4h, 4i, 4j have been synthesized and assayed for their antibacterial activity against Gram‐positive bacteria viz. Bacillus subtilis (ATCC 6633), Staphylococcus aureus (ATCC 6538p), Micrococcus luteus (IFC 12708), and Gram‐negative bacteria viz. Proteus vulgaris (ATCC 3851), Salmonella typhimurium (ATCC 14028), Escherichia coli (ATCC 25922), and also antifungal activity against Candida albicans (ATCC 10231), Aspergillus fumigatus (HIC 6094), Trichophyton rubrum (IFO 9185), and Trichophyton mentagrophytes (IFO 40996). Among the screened compounds, 4d, 4e, 4f, 4g, and 4j exhibited potent inhibitory activity compared with the standard drug at the tested concentrations. The results reveal that, the presence of difluorophenyl in 4f and pipernyl ring in 4j at 2‐position of thiazolidine‐4‐one ring show significant inhibitory activity. The other compounds also showed appreciable activity against the test bacteria and fungi and emerged as potential molecules for further development. J. Heterocyclic Chem., 2011.

  DOI：

  10.1002/jhet.505

文献信息

• Synthesis and antimicrobial activity of novel 2-(aryl)-3-[5-(2-oxo-2H-3-chromenyl)-1,3-oxazol-2-yl]-1,3-thiazolan-4-ones
  作者：Ch. Sanjeeva Reddy、M. Vani Devi、G. Rajesh Kumar、L. Sanjeeva Rao、A. Nagaraj

  DOI：10.1002/jhet.505

  日期：2011.1

  AbstractA series of novel 2‐(aryl)‐3‐[5‐(2‐oxo‐2H‐3‐chromenyl)‐1,3‐oxazol‐2‐yl]‐1,3‐thiazolan‐4‐ones 4a, 4b, 4c, 4e, 4f, 4g, 4h, 4i, 4j have been synthesized and assayed for their antibacterial activity against Gram‐positive bacteria viz. Bacillus subtilis (ATCC 6633), Staphylococcus aureus (ATCC 6538p), Micrococcus luteus (IFC 12708), and Gram‐negative bacteria viz. Proteus vulgaris (ATCC 3851), Salmonella typhimurium (ATCC 14028), Escherichia coli (ATCC 25922), and also antifungal activity against Candida albicans (ATCC 10231), Aspergillus fumigatus (HIC 6094), Trichophyton rubrum (IFO 9185), and Trichophyton mentagrophytes (IFO 40996). Among the screened compounds, 4d, 4e, 4f, 4g, and 4j exhibited potent inhibitory activity compared with the standard drug at the tested concentrations. The results reveal that, the presence of difluorophenyl in 4f and pipernyl ring in 4j at 2‐position of thiazolidine‐4‐one ring show significant inhibitory activity. The other compounds also showed appreciable activity against the test bacteria and fungi and emerged as potential molecules for further development. J. Heterocyclic Chem., 2011.