E-C-(2-butyl-4-chloro-1H-imidazol-5-yl)-N-phenylnitrone | 825645-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: E-C-(2-butyl-4-chloro-1H-imidazol-5-yl)-N-phenylnitrone
• 英文别名: E-C-(2-butyl-4-chloro-1H-imidazolyl)-N-phenyl nitrone
• CAS: 825645-30-5；825645-31-6
• 化学式: C₁₄H₁₆ClN₃O
• 分子量: 277.754
• InChiKey: NMWSSSRUUFEWTL-VCHYOVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.75
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  丙烯酸丁酯 、 E-C-(2-butyl-4-chloro-1H-imidazol-5-yl)-N-phenylnitrone 以 甲苯 为溶剂， 反应 38.0h， 生成 、 trans-2-(phenyl)-3-(2-butyl-4-chloro-1H-imidazolyl)-5-butylate isoxazoline
  参考文献：
  名称：

  Enhancement in antimicrobial activity of 2-(phenyl)-3-(2-butyl-4-chloro-1H-imidazolyl)-5-butylate isoxazolidine

  摘要：

  The trans rich isomer, 2-(phenyl)-3-(2-butyl-4-chloro-1H-imidazolyl)-5-butylate isoxazolidine A (> 96% ee) was synthesized by the condensation of E isomer rich nitrone 4 (> 98% ee) with butyl acrylate in an inert solvent. Obtained isoxazolidine was screened for its antifungal activity against Aspergillus niger, Cephalosporium acremonitum, Fusarium moniliforme by using Nystatin as positive control. It was also tested for its antibacterial activity against Bacillus subtilis, Escherichia coli, and Staphylococcus aureus by using Streptomycin as positive control. Enhanced antifungal activity was observed in isoxazolidine of > 96% ee compared to the isoxazolidine of > 69% ee (B), and enhancement was not observed in antibacterial activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.034
• 作为产物：
  描述：

  N-phenyl hydroxylamine hydrochloride 、 咪唑醛 在 Broensted acid 、 magnesium chloride 作用下， 以 二氯甲烷 为溶剂， 以67.2%的产率得到E-C-(2-butyl-4-chloro-1H-imidazol-5-yl)-N-phenylnitrone
  参考文献：
  名称：

  Enhancement in antimicrobial activity of 2-(phenyl)-3-(2-butyl-4-chloro-1H-imidazolyl)-5-butylate isoxazolidine

  摘要：

  The trans rich isomer, 2-(phenyl)-3-(2-butyl-4-chloro-1H-imidazolyl)-5-butylate isoxazolidine A (> 96% ee) was synthesized by the condensation of E isomer rich nitrone 4 (> 98% ee) with butyl acrylate in an inert solvent. Obtained isoxazolidine was screened for its antifungal activity against Aspergillus niger, Cephalosporium acremonitum, Fusarium moniliforme by using Nystatin as positive control. It was also tested for its antibacterial activity against Bacillus subtilis, Escherichia coli, and Staphylococcus aureus by using Streptomycin as positive control. Enhanced antifungal activity was observed in isoxazolidine of > 96% ee compared to the isoxazolidine of > 69% ee (B), and enhancement was not observed in antibacterial activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.034

文献信息

• Synthesis and microbial inhibition study of novel 5-imidazolyl substituted isoxazolidines
  作者：M.P. Sadashiva、H. Mallesha、N.A. Hitesh、K.S. Rangappa

  DOI：10.1016/j.bmc.2004.09.031

  日期：2004.12

  Cycloaddition of C-imidazolyl-N-phenylnitrotles with monosubstituted alkenes afforded 5-imidazolyl substituted isoxazolidines with high regioselectivity. Novel isoxazolidines were screened for their antibacterial activities against S. aureus, E. coli and B. subtilis by using streptomycin as a positive control. They were also tested for their antifungal activities against E moniliforme, A. niger and C. acremonium by using nystatin as a positive control. Isoxazolidines, 4a and 4f exhibited more potent inhibition towards antifungal activity than the other isoxazolidines prepared. (C) 2004 Elsevier Ltd. All rights reserved.