N-[2-(4-fluorophenyl)ethyl]-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-amine;chloride | 1350730-57-2

• 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-[2-(4-fluorophenyl)ethyl]-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-amine;chloride
• CAS: 1350730-57-2
• 化学式: C₂₇H₂₄FN₂O₃*Cl
• 分子量: 478.951
• InChiKey: YFRVNKDRKUAFFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氟苯乙胺 、 盐酸小檗碱 以 乙醇 为溶剂， 以63%的产率得到N-[2-(4-fluorophenyl)ethyl]-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-amine;chloride
  参考文献：
  名称：

  Synthesis, biological evaluation of 9-N-substituted berberine derivatives as multi-functional agents of antioxidant, inhibitors of acetylcholinesterase, butyrylcholinesterase and amyloid-β aggregation

  摘要：

  A series of 9-N-substituted berberine derivatives were synthesized and biologically evaluated as antioxidant and inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase and amyloid-beta aggregation. Most of these compounds exhibited very good antioxidant activities, inhibitive activities of AChE and amyloid-beta aggregation. Among them, compound 8d, (o-methylphenethyl)amino linked at the 9-position of berberine, was found to be a good antioxidant (with 4.05 mu M of Trolox equivalents), potent inhibitor of AChE (an IC50 value of 0.027 mu M), and high active inhibitor of amyloid-beta aggregation (an IC50 value of 2.73 mu M). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.051

文献信息

• Synthesis, biological evaluation of 9-N-substituted berberine derivatives as multi-functional agents of antioxidant, inhibitors of acetylcholinesterase, butyrylcholinesterase and amyloid-β aggregation
  作者：Wen-Jun Shan、Ling Huang、Qi Zhou、Fan-Chao Meng、Xing-Shu Li

  DOI：10.1016/j.ejmech.2011.09.051

  日期：2011.12

  A series of 9-N-substituted berberine derivatives were synthesized and biologically evaluated as antioxidant and inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase and amyloid-beta aggregation. Most of these compounds exhibited very good antioxidant activities, inhibitive activities of AChE and amyloid-beta aggregation. Among them, compound 8d, (o-methylphenethyl)amino linked at the 9-position of berberine, was found to be a good antioxidant (with 4.05 mu M of Trolox equivalents), potent inhibitor of AChE (an IC50 value of 0.027 mu M), and high active inhibitor of amyloid-beta aggregation (an IC50 value of 2.73 mu M). (C) 2011 Elsevier Masson SAS. All rights reserved.