16-[4-(4-Butyltriazol-1-yl)butoxy]-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-octaene;bromide | 1300563-18-1

• 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: 16-[4-(4-Butyltriazol-1-yl)butoxy]-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-octaene;bromide
• CAS: 1300563-18-1
• 化学式: Br*C₂₉H₃₃N₄O₄
• 分子量: 581.509
• InChiKey: FJTDJGYJNSKILZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  盐酸小檗碱 在 sodium azide 、 四丁基碘化铵 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 50.0~190.0 ℃ 、4.0 kPa 条件下， 反应 11.25h， 生成 16-[4-(4-Butyltriazol-1-yl)butoxy]-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-octaene;bromide
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling of novel triazole-containing berberine derivatives as acetylcholinesterase and β-amyloid aggregation inhibitors

  摘要：

  A series of novel triazole-containing berberine derivatives were synthesized via the azide-alkyne cycloaddition reaction. Their biological activity as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. Among them, compound 16d, which featured a diisopropylamino substitution at the 4-position of triazole ring, was found to be a potent inhibitor of AChE, with IC50 value of 0.044 mu M. Compound 18d, which beares a butyl at the 4-position of the triazole ring, showed the highest potency of beta-amyloid aggregation inhibition (77.9% at 20 mu M). Molecular modeling studies indicated that the triazole moiety of berberine derivatives displayed a face-to-face pi-pi stacking interaction in a 'sandwich' form with the Trp84 (4.09 angstrom) and Phe330 (4.33 angstrom) in catalytic sites of AChE. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.025

文献信息

• Synthesis, biological evaluation and molecular modeling of novel triazole-containing berberine derivatives as acetylcholinesterase and β-amyloid aggregation inhibitors
  作者：Anding Shi、Ling Huang、Chuanjun Lu、Feng He、Xingshu Li

  DOI：10.1016/j.bmc.2011.02.025

  日期：2011.4

  A series of novel triazole-containing berberine derivatives were synthesized via the azide-alkyne cycloaddition reaction. Their biological activity as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. Among them, compound 16d, which featured a diisopropylamino substitution at the 4-position of triazole ring, was found to be a potent inhibitor of AChE, with IC50 value of 0.044 mu M. Compound 18d, which beares a butyl at the 4-position of the triazole ring, showed the highest potency of beta-amyloid aggregation inhibition (77.9% at 20 mu M). Molecular modeling studies indicated that the triazole moiety of berberine derivatives displayed a face-to-face pi-pi stacking interaction in a 'sandwich' form with the Trp84 (4.09 angstrom) and Phe330 (4.33 angstrom) in catalytic sites of AChE. (C) 2011 Elsevier Ltd. All rights reserved.