(-)-N-methylcanadine iodide | 61774-67-2

• 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-methylcanadine iodide
• 英文别名: N-methylcanadinium iodide；9,10-dimethoxy-7ξ-methyl-(13ar)-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolinium; iodide；N-methyltetrahydroberberinium iodide；(+/-)-N-Methyltetrahydroepiberberiniumjodid；(+/-)-N-Methyl-tetrahydroberberinium；(+/-)-Tetrahydroberberin-methoiodid；N-Methylcanadium (iodide)；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;iodide
• CAS: 61774-67-2
• 化学式: C₂₁H₂₄NO₄*I
• 分子量: 481.33
• InChiKey: AZXUCIMPDKYWNT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.24
• 重原子数：
  27
• 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：
  5

反应信息

• 作为反应物：
  描述：

  (-)-N-methylcanadine iodide 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 双氧水 、 sodium acetate 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 苯 为溶剂， 反应 7.5h， 生成 别隐品碱
  参考文献：
  名称：

  从 Berbines 到 Protopines：区域控制的霍夫曼消除/氢化/氧化 N-取代的铼盐

  摘要：

  基于 N-（芳甲基）铼盐的顺序 Hofmann 消除、硼氢化和氧化反应，设计了一种改进的 protopines 合成方法。通过使用氯化小檗碱作为起始原料，这一系列反应提供了两种新的非天然原

  DOI：

  10.1002/ejoc.200500573
• 作为产物：
  描述：

  四氢小檗碱 、 碘甲烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 36.0h， 以68%的产率得到(-)-N-methylcanadine iodide
  参考文献：
  名称：

  Berberine Analogues as a Novel Class of the Low-Density-Lipoprotein Receptor Up-Regulators: Synthesis, Structure−Activity Relationships, and Cholesterol-Lowering Efficacy

  摘要：

  Twenty-nine derivatives of berberine (1) or pseudoberberine (2) were designed, semisynthesized, and evaluated for their up-regulatory activity on the low-density-lipoprotein receptor (LDLR) expression. SAR analysis revealed that (i) the methylenedioxy group at the 2- and 3-position is an essential element to keep the activity, (ii) the 7-position quaternary ammonium and planar structure of the compound are activity-required, and (iii) addition of electron-donating groups at the 7- or 13-position reduced the activity. Of the compound I analogues, compound 2 exhibited an increased activity on LDLR expression compared to 1. In the hyperlipidemic rats, compound 2 (100 (mg/kg)/day) reduced blood CHO and LDL-c by 42.6% and 49.4%, respectively, more efficient than I did (p < 0.01 for both). The results were confirmed in the hyperlipidemic mice. LD50 of 2 in mice was over 5000 mg/kg (oral). We consider compound 2 a promising cholesterol-lowering drug candidate.

  DOI：

  10.1021/jm801157z

文献信息

• Conversion of tetrahydroberberine into pavinane-type alkaloids
  作者：Kazuo Ito、Hiroshi Furukawa、Toshiyuki Iida、Kuo-Hsiung Lee、Taito O. Soine

  DOI：10.1039/c39740001037

  日期：——

  OO-Dimethylmunitagine (III) has been synthesised from tetrahydroberberine (V) through a series of reactions which culminate in the Stevens rearrangement.

  通过四氢小ber碱（V）经过一系列反应最终达到史蒂文斯重排反应，从四氢小methyl碱（V）合成了OO-二甲基单宁（III）。
• Simanek,V. et al., Collection of Czechoslovak Chemical Communications, 1970, vol. 35, p. 1440 - 1455
  作者：Simanek,V. et al.

  DOI：——

  日期：——
• US3932384A
  申请人：——

  公开号：US3932384A

  公开（公告）日：1976-01-13
• Berberine Analogues as a Novel Class of the Low-Density-Lipoprotein Receptor Up-Regulators: Synthesis, Structure−Activity Relationships, and Cholesterol-Lowering Efficacy
  作者：Ying-Hong Li、Peng Yang、Wei-Jia Kong、Yan-Xiang Wang、Chang-Qin Hu、Zeng-Yan Zuo、Yue-Ming Wang、Hong Gao、Li-Mei Gao、Yan-Chun Feng、Na-Na Du、Ying Liu、Dan-Qing Song、Jian-Dong Jiang

  DOI：10.1021/jm801157z

  日期：2009.1.22

  Twenty-nine derivatives of berberine (1) or pseudoberberine (2) were designed, semisynthesized, and evaluated for their up-regulatory activity on the low-density-lipoprotein receptor (LDLR) expression. SAR analysis revealed that (i) the methylenedioxy group at the 2- and 3-position is an essential element to keep the activity, (ii) the 7-position quaternary ammonium and planar structure of the compound are activity-required, and (iii) addition of electron-donating groups at the 7- or 13-position reduced the activity. Of the compound I analogues, compound 2 exhibited an increased activity on LDLR expression compared to 1. In the hyperlipidemic rats, compound 2 (100 (mg/kg)/day) reduced blood CHO and LDL-c by 42.6% and 49.4%, respectively, more efficient than I did (p < 0.01 for both). The results were confirmed in the hyperlipidemic mice. LD50 of 2 in mice was over 5000 mg/kg (oral). We consider compound 2 a promising cholesterol-lowering drug candidate.
• From Berbines to Protopines: Regiocontrolled Hofmann Elimination/Hydroboration/Oxidation ofN-Substituted Berbinium Salts
  作者：María Valpuesta、Amelia Díaz、Rafael Suau、Gregorio Torres

  DOI：10.1002/ejoc.200500573

  日期：2006.2

  An improved synthetic approach to protopines based on the sequential Hofmann elimination, hydroboration and oxidation of N-(arylmethyl)berbinium salts has been designed. By using berberine chloride as the starting material, this sequence of reactions has provided two new nonnatural proto

  基于 N-（芳甲基）铼盐的顺序 Hofmann 消除、硼氢化和氧化反应，设计了一种改进的 protopines 合成方法。通过使用氯化小檗碱作为起始原料，这一系列反应提供了两种新的非天然原