9-O-[4-(phenyloxy)butyl]berberine bromide | 1219819-26-7

• 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-O-[4-(phenyloxy)butyl]berberine bromide
• 英文别名: 17-Methoxy-16-(4-phenoxybutoxy)-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: 1219819-26-7
• 化学式: Br*C₂₉H₂₈NO₅
• 分子量: 550.449
• InChiKey: RGAFBRYQCWMODS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  50
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-苯氧基丁基溴 、 berberrubine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以76%的产率得到9-O-[4-(phenyloxy)butyl]berberine bromide
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular modeling of berberine derivatives as potent acetylcholinesterase inhibitors

  摘要：

  By targeting the dual active sites of acetylcholinesterase (AChE), a new series of berberine derivatives was designed, synthesized, and evaluated as AChE inhibitors. Most of the derivatives inhibited AChE in the sub-micromolar range. Compound 8c, berberine linked with phenol by a 4-carbon spacer, showed the most potent inhibition of AChE. A kinetic study of AChE and BuChE indicated that a mix-competitive binding mode existed for these berberine derivatives. Molecular modeling studies confirmed that these hybrids target both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. This is the first report where AChE inhibitory activity has been associated with berberine as a lead molecule. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.035

文献信息

• [EN] APPLICATION OF TETRACYCLIC COMPOUND IN TREATMENT OF TUMORS<br/>[FR] APPLICATION D'UN COMPOSÉ TÉTRACYCLIQUE DANS LE TRAITEMENT DE TUMEURS<br/>[ZH] 四环类化合物在治疗肿瘤中的应用
  申请人：[en]NANJING SHIJIANG MEDICINE TECHNOLOGY CO., LTD;[zh]南京施江医药科技有限公司

  公开号：WO2023169567A1

  公开（公告）日：2023-09-14

  本发明涉及四环类化合物在治疗肿瘤中的应用，具体地，本发明提供一种式I化合物、或其光学异构体或其外消旋体、或其溶剂化物、或其药学上可接受的盐、或其氘代化合物的用途，用于制备组合物或制剂，所述组合物或制剂用于预防和/或治疗肿瘤。本发明所述的化合物对NNMT基因低表达或未表达、DNA甲基化酶高表达、UHRF1高表达、NNMT基因核苷酸位点甲基化水平高和/或NNMT基因区DNA CpG位点甲基化水平高的肿瘤具有优异的精准化治疗效果。
• Synthesis, biological evaluation, and molecular modeling of berberine derivatives as potent acetylcholinesterase inhibitors
  作者：Ling Huang、Anding Shi、Feng He、Xingshu Li

  DOI：10.1016/j.bmc.2009.12.035

  日期：2010.2

  By targeting the dual active sites of acetylcholinesterase (AChE), a new series of berberine derivatives was designed, synthesized, and evaluated as AChE inhibitors. Most of the derivatives inhibited AChE in the sub-micromolar range. Compound 8c, berberine linked with phenol by a 4-carbon spacer, showed the most potent inhibition of AChE. A kinetic study of AChE and BuChE indicated that a mix-competitive binding mode existed for these berberine derivatives. Molecular modeling studies confirmed that these hybrids target both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. This is the first report where AChE inhibitory activity has been associated with berberine as a lead molecule. (C) 2009 Elsevier Ltd. All rights reserved.