N-(3-chlorobenzyl)-N-(2-(4-nitro-1H-imidazol-1-yl)ethyl)-2-(2-berberinoxyethoxy)ethanamine | 1383981-98-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: N-(3-chlorobenzyl)-N-(2-(4-nitro-1H-imidazol-1-yl)ethyl)-2-(2-berberinoxyethoxy)ethanamine
• 英文别名: N-[(3-chlorophenyl)methyl]-N-[2-[(17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-yl)oxy]ethyl]-2-(4-nitroimidazol-1-yl)ethanamine;chloride
• CAS: 1383981-98-3
• 化学式: C₃₃H₃₁ClN₅O₆*Cl
• 分子量: 664.545
• InChiKey: WPUNTGZQHYYFQL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-bromo-N-(2-bromoethyl)-N-(3-chlorobenzyl)ethanamine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 23.0h， 生成 N-(3-chlorobenzyl)-N-(2-(4-nitro-1H-imidazol-1-yl)ethyl)-2-(2-berberinoxyethoxy)ethanamine
  参考文献：
  名称：

  Synthesis and bioactive evaluation of novel hybrids of metronidazole and berberine as new type of antimicrobial agents and their transportation behavior by human serum albumin

  摘要：

  A series of novel hybrids of metronidazole and berberine as new type of antimicrobial agents were synthesized and characterized by H-1 NMR, C-13 NMR, IR, MS and FIRMS spectra. Bioactive assay manifested that most of the prepared compounds exhibited effective antibacterial and antifungal activities and some showed comparable or superior potency against Methicillin-resistant Staphylococcus aureus to reference drugs Norfloxacin, Chloromycin and Berberine. The transportation behavior of human serum albumin (HSA) to the highly active compound 5g was evaluated and revealed that the association of imidazole derivative 5g with HSA was spontaneous and the electrostatic interactions played important roles in the transportation of HSA to 5g. The calculated parameters indicated that compound 5g could be effectively stored and carried by HSA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.007

文献信息

• Synthesis and bioactive evaluation of novel hybrids of metronidazole and berberine as new type of antimicrobial agents and their transportation behavior by human serum albumin
  作者：Ling Zhang、Juan-Juan Chang、Shao-Lin Zhang、Guri L.V. Damu、Rong-Xia Geng、Cheng-He Zhou

  DOI：10.1016/j.bmc.2013.05.007

  日期：2013.7

  A series of novel hybrids of metronidazole and berberine as new type of antimicrobial agents were synthesized and characterized by H-1 NMR, C-13 NMR, IR, MS and FIRMS spectra. Bioactive assay manifested that most of the prepared compounds exhibited effective antibacterial and antifungal activities and some showed comparable or superior potency against Methicillin-resistant Staphylococcus aureus to reference drugs Norfloxacin, Chloromycin and Berberine. The transportation behavior of human serum albumin (HSA) to the highly active compound 5g was evaluated and revealed that the association of imidazole derivative 5g with HSA was spontaneous and the electrostatic interactions played important roles in the transportation of HSA to 5g. The calculated parameters indicated that compound 5g could be effectively stored and carried by HSA. (C) 2013 Elsevier Ltd. All rights reserved.