13-甲基小檗红碱 | 53912-30-4

• 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
• 中文名称: 13-甲基小檗红碱
• 英文名称: 13-methylberberrubine
• 英文别名: 17-Methoxy-21-methyl-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,14,17,19-heptaen-16-one；17-methoxy-21-methyl-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,14,17,19-heptaen-16-one
• CAS: 53912-30-4
• 化学式: C₂₀H₁₈NO₄
• 分子量: 336.367
• InChiKey: GNGXWKSHOCHZLN-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  13-甲基小檗红碱 在 盐酸 、 锌 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (9-OCD3)mesothalictricavine
  参考文献：
  名称：

  Biotransformations of protoberberines in cell cultures of Dicentra spectablis

  摘要：

  A liquid chromatography-atmospheric pressure chemical ionization mass spectrometry procedure was applied to biotransformation experiments in cultured cells of Dicentra spectablis. Interconversions of tetrahydroberberine and berberine and those of cis-and trans-13-methyltetrahydroprotoberberine and 13-methylberberine were demonstrated. The corresponding alpha-N-metho salts having the BIC-cis ring-junction were produced from cis-and trans-13-methyltetrahydroprotoberberine These findings show that the metabolism of protoberberines in D. spectablis proceeds analogously to that found in Cordyalis species. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0031-9422(97)00500-1
• 作为产物：
  描述：

  dehydrthalictricavine 210.0~230.0 ℃ 、4.0 kPa 条件下， 反应 0.17h， 生成 13-甲基小檗红碱
  参考文献：
  名称：

  Biotransformations of protoberberines in cell cultures of Dicentra spectablis

  摘要：

  A liquid chromatography-atmospheric pressure chemical ionization mass spectrometry procedure was applied to biotransformation experiments in cultured cells of Dicentra spectablis. Interconversions of tetrahydroberberine and berberine and those of cis-and trans-13-methyltetrahydroprotoberberine and 13-methylberberine were demonstrated. The corresponding alpha-N-metho salts having the BIC-cis ring-junction were produced from cis-and trans-13-methyltetrahydroprotoberberine These findings show that the metabolism of protoberberines in D. spectablis proceeds analogously to that found in Cordyalis species. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0031-9422(97)00500-1

文献信息

• USE AND PREPARATION METHOD OF BERBERINE COMPOUNDS
  申请人：DALIAN INSTITUTE OF CHEMICAL PYSICS, CHINESE ACADEMY OF SCIENCES

  公开号：US20150164870A1

  公开（公告）日：2015-06-18

  A method of treating nervous system diseases associated with dopamine receptors comprising administering a patent in need a compound having a structure of general formula (I) or a pharmaceutical acceptable salt, hydrate, or solvate thereof in a pharmaceutically effective amount, and a method of making the compound having the structure of general formula (I) or a pharmaceutical acceptable salt, hydrate, or solvate thereof. The compound of formula (I) has multiple pharmacological functions such as the functions of activating opioid receptors and blocking dopamine D2 receptors, and has good physicochemical properties and oral bioavailability. General animal experiments show that such a compound has significant and long-lasting analgesic and calming effects and can be used to treat pain and other mental illnesses.

  一种治疗与多巴胺受体相关的神经系统疾病的方法，包括向需要的患者施用具有一般式(I)结构的化合物或其药用可接受的盐、水合物或溶剂化合物，以药学有效量，并制备具有一般式(I)结构的化合物或其药用可接受的盐、水合物或溶剂化合物的方法。式(I)的化合物具有多种药理功能，如激活阿片受体和阻断多巴胺D2受体的功能，并具有良好的理化性质和口服生物利用度。一般动物实验显示，这种化合物具有显著且持久的镇痛和镇静作用，可用于治疗疼痛和其他精神疾病。
• 一种模块化地多样性地合成苯并菲啶类和原小檗碱类生物碱的方法
  申请人：华东师范大学

  公开号：CN112851661B

  公开（公告）日：2022-12-06

  本发明公开了一种模块化地多样性地调控合成苯并菲啶类和原小檗碱类生物碱的方法，所述方法通过改进高碘盐离去基团的取代基，在相对温和的叔丁醇钾的作用下产生吡啶炔，与双烯体发生[4+2]环加成反应，得到一类多取代的异喹啉环前体化合物。通过开发新型的铱催化交叉偶联的方法实现这类异喹啉环前体的开环及芳构化，高效合成具有连接能力的多取代的异喹啉环类化合物，随后与一类高活性的多取代的环状硼酸发生偶联，继而得到一类3‑芳基异喹啉高级中间体。通过两种不同化学原理的应用，实现对这类3‑芳基异喹啉高级中间体的调控，模块化地多样性地高效地合成苯并菲啶类和原小檗碱类生物碱。
• Method and composition for controlling oral pathogens
  申请人：Wu D. Christine

  公开号：US20070098649A1

  公开（公告）日：2007-05-03

  A composition and method of controlling oral and other human pathogens is disclosed. The composition and method utilize an antimicrobial or antibiotic and a berberine as active agents to treat mammals, including humans.
• US9610281B2
  申请人：——

  公开号：US9610281B2

  公开（公告）日：2017-04-04
• Biotransformations of protoberberines in cell cultures of Dicentra spectablis
  作者：Kinuko Iwasa、Chong Won Kim

  DOI：10.1016/s0031-9422(97)00500-1

  日期：1997.12

  A liquid chromatography-atmospheric pressure chemical ionization mass spectrometry procedure was applied to biotransformation experiments in cultured cells of Dicentra spectablis. Interconversions of tetrahydroberberine and berberine and those of cis-and trans-13-methyltetrahydroprotoberberine and 13-methylberberine were demonstrated. The corresponding alpha-N-metho salts having the BIC-cis ring-junction were produced from cis-and trans-13-methyltetrahydroprotoberberine These findings show that the metabolism of protoberberines in D. spectablis proceeds analogously to that found in Cordyalis species. (C) 1997 Elsevier Science Ltd.