2,3,9,10-tetrahydroxyprotoberberine

• 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: 2,3,9,10-tetrahydroxyprotoberberine
• 英文别名: 2,3,9,10-tetrahydroxyberberine；Berberolinium；5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2,3,9,10-tetrol
• 化学式: C₁₇H₁₄NO₄
• 分子量: 296.302
• InChiKey: DAHMYCXNJSCLGA-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.8
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,9,10-tetrahydroxyprotoberberine 在 sodium tetrahydroborate 、 碘 、 sodium acetate 、 potassium carbonate 作用下， 以 乙醇 、 溶剂黄146 、 乙腈 为溶剂， 反应 7.5h， 生成 2,3,9,10-tetrabutoxyprotoberberine
  参考文献：
  名称：

  一种由黄连混合生物碱制备2,3,9,10-四丁氧基原小檗碱的方法

  摘要：

  本发明提供一种由黄连混合生物碱制备2,3,9,10‑四丁氧基原小檗碱的方法，黄连混合生物碱是由具有共同异喹啉环结构成分的黄连碱、巴马汀，小檗碱和药根碱等四种主要成分所组成的。黄连混合生物碱经脱甲氧基或亚甲二氧基、还原、丁基化和氧化四步反应完成生物碱的转化，制得2,3,9,10‑四丁氧基原小檗碱。本发明通过化学修饰手段直接将具有异喹啉类结构的黄连混合生物碱转化为2,3,9,10‑四丁氧基原小檗碱，不用复杂的提纯和分离，与已有技术相比，所有步骤的反应温度更低，时间更短，大大节省了能源和成本。材料的配比更合理，操作方法简便，所以收率更高，四氢2,3,9,10‑四丁氧基原小檗碱的收率为62%。适合2,3,9,10‑四丁氧基原小檗碱的批量生产。

  公开号：

  CN106117197A
• 作为产物：
  描述：

  小檗碱 在 氢碘酸 作用下， 以0.8 g的产率得到2,3,9,10-tetrahydroxyprotoberberine
  参考文献：
  名称：

  Gastric-Mucous Membrane Protection Activity of Coptisine Derivatives.

  摘要：

  从黄连块根中分离出Coptisine和8-oxocoptisine作为胃粘膜保护的主要成分。这两种化合物比西咪替丁和硫糖醇显示出更强的活性。我们使用市售起始材料合成了几种具有Coptisine部分结构的衍生物。获得的化合物经过了胃粘膜保护活性测试，并研究了活性与结构之间的相关性。我们的结果表明，儿茶酚骨架的部分电荷与活性相关。

  DOI：

  10.1248/bpb.24.1277

文献信息

• Compounds and Compositions for Modulating Lipid Levels and Methods of Preparing Same
  申请人：Liu Haiyan

  公开号：US20110009628A1

  公开（公告）日：2011-01-13

  The present technology relates to compounds of Formulas I-VI and methods of making and using such compounds. Methods of use include prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Compounds disclosed herein also increase HDL-C, lower total cholesterol, LDL-cholesterol, and triglycerides and increase hepatic LDL receptor expression, inhibit PCSK9 expression, and activate AMP-activated protein kinase.

  目前的技术涉及到公式I-VI的化合物以及制备和使用这些化合物的方法。使用方法包括预防和治疗高脂血症、高胆固醇血症、高甘油三酯血症、肝脂肪变性和代谢综合征。本文披露的化合物还可以增加高密度脂蛋白胆固醇（HDL-C），降低总胆固醇、低密度脂蛋白胆固醇（LDL-C）和甘油三酯，并增加肝LDL受体表达，抑制PCSK9表达，并激活AMP激活蛋白激酶。
• COMPOUNDS AND METHODS FOR MODULATING RHO GTPASES
  申请人：Leblond Bertrand

  公开号：US20100120810A1

  公开（公告）日：2010-05-13

  The present invention relates to methods and compositions that affect the GTP-binding activity of members of the Rho family GTPases, preferably Rac GTPases (Rac1, Rac1b, Rac2 and/or Rac3).

  本发明涉及影响Rho家族GTP酶成员的GTP结合活性的方法和组合物，优选是Rac GTP酶（Rac1，Rac1b，Rac2和/或Rac3）。
• BERBERINE SALTS, URSODEOXYCHOLIC SALTS AND COMBINATIONS, METHODS OF PREPARATION AND APPLICATION THEREOF
  申请人：SHENZHEN HIGHTIDE BIOPHARMACEUTICAL, LTD.

  公开号：US20170037043A1

  公开（公告）日：2017-02-09

  The invention provides various novel compositions of berberine in combination with pharmacologically active organic acids, and related methods of their use in treating various diseases or disorders. The invention further provides various novel compounds prepared from berberine and pharmacologically active organic acids and prepared from ursodeoxycholic acid and pharmacologically active organic bases, and pharmaceutical compositions thereof, and methods of their preparation and therapeutic use in treating and/or preventing various diseases or disorders. The compounds and pharmaceutical compositions of the invention can be utilized to treat various diseases or disorders, such as diabetes, diabetic complications, dyslipidemia, hyperlipidemia, obesity, metabolic syndromes, pre-diabetes, atherosclerosis, heart diseases, neurodegenerative diseases, sarcopenia, muscle atrophy, inflammation, cancer and liver diseases and conditions such as fatty liver, non-alcoholic fatty liver disease, non-alcoholic steatohepatitis, cholestatic liver diseases or graft-versus-host disease of the liver. The compounds of this invention are also useful in improving liver functions in chronic viral associated liver diseases and alcohol-related liver diseases.
• CONJUGATE COMPOUNDS OF URSODEOXYCHOLIC, BERBERINE OR L-CARNITINE, AND COMPOSITIONS AND METHODS THEREOF
  申请人：SHENZHEN HJGHTIDE-BIOPHARMAGEUTiCAL, LTD.

  公开号：US20180050048A1

  公开（公告）日：2018-02-22

  The invention provides novel conjugate compounds having at least one of a moiety derived from ursodeoxycholic acid, or eicosapentaenoic acid, or docosahexaenoic acid, or rhein, or R-(+)-α-lipoic acid, or ursolic acid, or corosolic acid, or hydroxycitric acid, or cinnamic acid, or cholic acid, or oleanolic acid, or salicylic acid, or betulinic acid, or chlorogenic acid, or caffeic acid, or bassic acid, or acetyl L-carnitine, or S-allyl cysteine sulphoxide, or S-methyl cysteine sulfoxide, or pantothenic acid, or ascorbic acid, or retinoic acid, or nicotinic acid, or biotin, or a derivative or analog thereof, and a moiety derived from berberine or L-carnitine or metformin or unsaturated fatty acid, or a derivative or analog thereof. The invention also relates to pharmaceutical compositions, methods of preparation and use of these conjugates in treating and/or preventing, for example, liver diseases or disorders, various diabetes, diabetic complications, dyslipidemia, obesity, metabolic syndromes, pre-diabetes, muscle atrophy, inflammation, and cancers. The compounds of this invention are also useful in improving liver functions in chronic viral associated liver diseases and alcohol-related liver diseases.
• [EN] BERBERINE DERIVATIVES USEFUL FOR MODULATING LIPID LEVELS AND THEIR METHODS OF SYNTHESIS<br/>[FR] DÉRIVÉS DE LA BERBÉRINE UTILES POUR MODULER LES NIVEAUX LIPIDIQUES ET LEURS PROCÉDÉS DE SYNTHÈSE
  申请人：LIU HAIYAN

  公开号：WO2011006000A1

  公开（公告）日：2011-01-13

  The present technology relates to compounds of Formulas I-VI and methods of making and using such compounds. Methods of use include prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Compounds disclosed herein also increase HDL-C, lower total cholesterol, LDL-cholesterol, and triglycerides and increase hepatic LDL receptor expression, inhibit PCSK9 expression, and activate AMP-activated protein kinase.