N-methyl tetrahydroberberine | 26297-11-0

• 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-methyl tetrahydroberberine
• 英文别名: N-methyltetrahydroberberine；N‐methylcanadine；(R,S)-N-methylcanadine；N-methylcanadine；9,10-dimethoxy-7ξ-methyl-(13ar)-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolinium；(+/-)-N-methyl-tetrahydro-berberinium；alpha-Canadine methochloride；16,17-dimethoxy-13-methyl-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene
• CAS: 26297-11-0
• 化学式: C₂₁H₂₄NO₄
• 分子量: 354.426
• InChiKey: IPABSWBNWMXCHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl tetrahydroberberine 在 S₉ protein 、 还原型辅酶II(NADPH)四钠盐 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  高效液相色谱/四极杆飞行时间质谱法表征大鼠肝脏S9中的N-甲基卡丹汀和N-甲基苯乙烯碱代谢产物。

  摘要：

  RATIONALE N-甲基犬胺碱和N-甲基苯乙烯碱是两种异喹啉生物碱，被认为是罂粟科的主要药用活性成分。然而，迄今为止，尚未有关于N-甲基卡丹汀和N-甲基苯乙烯的代谢研究的报道。因此，本研究的目的是研究这两种生物碱在大鼠肝脏S9中的体外代谢。方法将N-甲基犬精或N-甲基苯乙烯丁与大鼠肝脏S9一起孵育1小时，然后用15％三氯乙酸处理。使用高效液相色谱和四极杆飞行时间质谱（HPLC / QqTOF-MS）作为可靠的分析方法。这些代谢物的结构表征是通过准确的MS / MS光谱和已知的元素组成进行的。结果，初步鉴定出大鼠肝S9中总共有4种N-甲基卡丹汀代谢物和5种N-甲基stylopine代谢物。药物的亚甲二氧基的裂解是N-甲基卡丹汀和N-甲基苯乙烯的主要代谢途径。结论本研究是使用可靠的HPLC / QqTOF-MS方法首次对大鼠肝脏S9中N-甲基卡丹汀和N-甲基stylopine进行体外代谢研

  DOI：

  10.1002/rcm.8286
• 作为产物：
  描述：

  小檗碱 在 盐酸 、 锌 作用下， 反应 5.0h， 生成 N-methyl tetrahydroberberine
  参考文献：
  名称：

  Synthesis and antihyperglycemic evaluation of various protoberberine derivatives

  摘要：

  Various berberine derivatives (2-17) were synthesized and their antihyperglycemic activities were evaluated in a model of beta-cell-membrane chromatography and a model of alloxan-induced diabetes mice. The results indicated that compounds 5 and 14 exhibited antihyperglycemic activity. Their structure-activity relationships were discussed. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.045

文献信息

• Facile synthesis of tetrahydroprotoberberine and protoberberine alkaloids from protopines and study on their antibacterial activities
  作者：Pi Cheng、Bin Wang、Xiubin Liu、Wei Liu、Weisong Kang、Jie Zhou、Jianguo Zeng

  DOI：10.1080/14786419.2013.867344

  日期：2014.4.3

  A series of isoquinoline alkaloids including tetrahydroprotoberberines, N-methyl tetrahydroprotoberberines and protoberberines were facile synthesised with protopines as the starting material. All compounds were evaluated for their antibacterial activities against four pathogenic bacteria Escherichia coli, Staphyloccocus aureus, Staphylococcus gallinarum and Salmonella choleraesuis. Experimental results

  以protopines为起始原料，容易合成包括四氢小pro碱，N-甲基四氢小ber碱和小ine碱在内的一系列异喹啉生物碱。评价了所有化合物对四种病原菌大肠杆菌，金黄色葡萄球菌，鸡葡萄球菌和霍乱沙门氏菌的抗菌活性。实验结果表明，原小ber碱是被测生物碱中对靶细菌活性最高的化合物。有人提出，具有较高芳香化水平的平面分子（例如黄连5和小ber碱6））或分子的正电荷（例如N-甲基四氢小pro碱11和12）对抗菌作用具有积极影响。
• Compositions and methods for making noscapine and synthesis intermediates thereof
  申请人：Willow BioSciences Inc.

  公开号：US10793885B2

  公开（公告）日：2020-10-06

  Methods for the manufacture of the therapeutic chemical compound noscapine and noscapine synthesis intermediates comprising contacting a noscapine pathway precursor selected from a first canadine derivative, a first papaveroxine derivative and narcotine hemiacetal with at least one of the enzymes selected from the group CYP82Y1, CYP82X1, AT1, CYP82X2, OMT, CXE1 and NOS.

  生产治疗用化学合成物诺卡平和诺卡平合成中间体的方法，包括将选自第一卡那定衍生物、第一罂粟碱衍生物和麻醉品半缩醛的诺卡平途径前体与选自CYP82Y1、CYP82X1、AT1、CYP82X2、OMT、CXE1和NOS组的至少一种酶接触。
• COMPOSITIONS AND METHODS FOR MAKING NOSCAPINE AND SYNTHESIS INTERMEDIATES THEREOF
  申请人：EPIMERON INC.

  公开号：US20160201101A1

  公开（公告）日：2016-07-14

  Methods for the manufacture of the therapeutic chemical compound noscapine and noscapine synthesis intermediates comprising contacting a noscapine pathway precursor selected from a first canadine derivative, a first papaveroxine derivative and narcotine hemiacetal with at least one of the enzymes selected from the group CYP82Y1, CYP82X1, AT1, CYP82X2, OMT, CXE1 and NOS.
• Synthesis and antihyperglycemic evaluation of various protoberberine derivatives
  作者：Xiaoli Bian、Langchong He、Guangde Yang

  DOI：10.1016/j.bmcl.2005.11.045

  日期：2006.3

  Various berberine derivatives (2-17) were synthesized and their antihyperglycemic activities were evaluated in a model of beta-cell-membrane chromatography and a model of alloxan-induced diabetes mice. The results indicated that compounds 5 and 14 exhibited antihyperglycemic activity. Their structure-activity relationships were discussed. (C) 2005 Elsevier Ltd. All rights reserved.
• Characterization of <i>N</i> -methylcanadine and <i>N</i> -methylstylopine metabolites in rat liver S9 by high-performance liquid chromatography/quadrupole time-of-flight mass spectrometry
  作者：Meng-Ting Zuo、Sha-Sha Liu、Li Lin、Zi-Yuan Wang、Xia Bai、Zhi-Liang Sun、Zhao-Ying Liu

  DOI：10.1002/rcm.8286

  日期：2018.12.15

  High-performance liquid chromatography with quadrupole time-of-flight mass spectrometry (HPLC/QqTOF-MS) as a reliable analytical method was used. The structural characterization of these metabolites was performed by the combination of the accurate MS/MS spectra and the known elemental composition. RESULTS As a result, a total of four metabolites of N-methylcanadine and five metabolites of N-methylstylopine

  RATIONALE N-甲基犬胺碱和N-甲基苯乙烯碱是两种异喹啉生物碱，被认为是罂粟科的主要药用活性成分。然而，迄今为止，尚未有关于N-甲基卡丹汀和N-甲基苯乙烯的代谢研究的报道。因此，本研究的目的是研究这两种生物碱在大鼠肝脏S9中的体外代谢。方法将N-甲基犬精或N-甲基苯乙烯丁与大鼠肝脏S9一起孵育1小时，然后用15％三氯乙酸处理。使用高效液相色谱和四极杆飞行时间质谱（HPLC / QqTOF-MS）作为可靠的分析方法。这些代谢物的结构表征是通过准确的MS / MS光谱和已知的元素组成进行的。结果，初步鉴定出大鼠肝S9中总共有4种N-甲基卡丹汀代谢物和5种N-甲基stylopine代谢物。药物的亚甲二氧基的裂解是N-甲基卡丹汀和N-甲基苯乙烯的主要代谢途径。结论本研究是使用可靠的HPLC / QqTOF-MS方法首次对大鼠肝脏S9中N-甲基卡丹汀和N-甲基stylopine进行体外代谢研