9-N-(2'-(phenyl)ethyl)berberine chloride | 1060705-12-5

• 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: 9-N-(2'-(phenyl)ethyl)berberine chloride
• 英文别名: 9-N-2'-(phenyl)ethylberberine；17-methoxy-N-(2-phenylethyl)-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: 1060705-12-5
• 化学式: C₂₇H₂₅N₂O₃*Cl
• 分子量: 460.96
• InChiKey: OXNNJOPPFIDIDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  33
• 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：
  5

反应信息

• 作为产物：
  描述：

  盐酸小檗碱 、 2-苯乙胺 以 乙醇 为溶剂， 以60%的产率得到9-N-(2'-(phenyl)ethyl)berberine 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

• 9-N-Substituted berberine derivatives: Stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc
  作者：Yan Ma、Tian-Miao Ou、Jin-Qiang Hou、Yu-Jing Lu、Jia-Heng Tan、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.bmc.2008.07.029

  日期：2008.8

  A series of 9-N-substituted berberine derivatives (2a-j) were synthesized and evaluated as a new class of G-quadruplex binding ligands. G-quadruplex of DNA had been proven to be the transcription controller of human c-myc gene. The interaction of 9-N-substituted berberine derivatives with G-quadruplex DNA in c-myc was examined via EMSA, CD spectroscopy, FRET-melting method, PCR-stop assay, competitive dialysis, cell proliferation assay and RT-PCR assay. The experiment results indicated that these derivatives could selectively induce and stabilize the formation of intramolecular parallel G-quadruplex in c-myc, which led to down-regulation of transcription of the c-myc in the HL60 lymphomas cell line. The related structure-activity relationships were also discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.