13-hydroxyberberine | 5058-45-7

• 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: 13-hydroxyberberine
• 英文别名: Neo-Oxyberberine；16,17-dimethoxy-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-octaen-21-ol
• CAS: 5058-45-7
• 化学式: C₂₀H₁₈NO₅
• 分子量: 352.367
• InChiKey: WPQJUYMGQNBENF-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氯甲酸乙酯 、 13-hydroxyberberine 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以46%的产率得到13-Ethoxycarbonyloxy-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; chloride
  参考文献：
  名称：

  Structure-activity relationships of quaternary protoberberine alkaloids having an antimalarial activity

  摘要：

  Seventeen quaternary protoberberine alkaloids related to berberine I were tested for antimalarial activity in vitro against Plasmodium falciparum and structure-activity relationships are proposed. The activity of the protoberberine alkaloids was influenced by the type of the oxygen substituents on rings A, C and D and the position of the oxygen functions on ring D. The position of the oxygen functions on ring D and the type of the oxygen substituents at the C-13 position (ring C) strongly influenced the activity. Shifting the oxygen functions at C-9 and C-10 to C-10 and C-Il on ring D resulted in a significant increase in the activity. Compounds bearing a methylenedioxy function at C-2 and C-3 (ring A) or C-9 and C-IO (ring D) showed higher activity than those which have methoxy groups at the same positions. Introduction of a methoxy group into the C-l position (ring A) decreased the activity. Replacement of a hydroxy group at C-2 or C-3 (ring A) by a methoxy group led to a reduction in the activity. Displacement of a hydroxy function at C-13 (ring C) by the oxygen substituents such as OMe, Oft, OCOOEt, and OCON(Me)(2) reduced the activity. In the same replacement at C-9 (ring D), the activity depended upon the type of the oxygen function. Six protoberberines displayed more potent activity than berberine 1. The activity decreased in the order: 10, 11, 17 and 18 > 7 and 8 > 1. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00127-0

文献信息

• 13,13a-DIHYDROBERBERINE DERIVATIVES, THEIR PHARMACEUTICAL COMPOSITION AND USE
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP2070926A1

  公开（公告）日：2009-06-17

  The present invention provides 13,13a-dihydroberberine derivatives or their physiologically acceptable salts represented by the following formula, pharmaceutical compositions comprising the same, and uses thereof. The 13,13a-dihydroberberine derivatives have an activity of promoting glucose absorption in muscle cells, and the whole animal tests show that the present compounds have effects on improving glucose-tolerance and insulin-resistance, facilitating weight loss, relieving fatty liver and the like. Thus, the present compounds can be used in treating diabetes mellitus, adiposity, fatty liver and complications thereof induced by insulin resistance.

  本发明提供了由下式表示的13,13a-二氢小檗碱衍生物或其生理上可接受的盐、由其组成的药物组合物及其用途。13,13a-二氢小檗碱衍生物具有促进肌肉细胞吸收葡萄糖的活性，整体动物试验表明，本发明化合物具有改善糖耐量和胰岛素抵抗、促进减肥、缓解脂肪肝等作用。因此，本化合物可用于治疗胰岛素抵抗引起的糖尿病、肥胖症、脂肪肝及其并发症。
• 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.
• Structure-activity relationships of quaternary protoberberine alkaloids having an antimalarial activity
  作者：Kinuko Iwasa、Yumi Nishiyama、Momoyo Ichimaru、Masataka Moriyasu、Hye-Sook Kim、Yusuke Wataya、Takao Yamori、Turuo Takashi、Dong-Ung Lee

  DOI：10.1016/s0223-5234(99)00127-0

  日期：1999.12

  Seventeen quaternary protoberberine alkaloids related to berberine I were tested for antimalarial activity in vitro against Plasmodium falciparum and structure-activity relationships are proposed. The activity of the protoberberine alkaloids was influenced by the type of the oxygen substituents on rings A, C and D and the position of the oxygen functions on ring D. The position of the oxygen functions on ring D and the type of the oxygen substituents at the C-13 position (ring C) strongly influenced the activity. Shifting the oxygen functions at C-9 and C-10 to C-10 and C-Il on ring D resulted in a significant increase in the activity. Compounds bearing a methylenedioxy function at C-2 and C-3 (ring A) or C-9 and C-IO (ring D) showed higher activity than those which have methoxy groups at the same positions. Introduction of a methoxy group into the C-l position (ring A) decreased the activity. Replacement of a hydroxy group at C-2 or C-3 (ring A) by a methoxy group led to a reduction in the activity. Displacement of a hydroxy function at C-13 (ring C) by the oxygen substituents such as OMe, Oft, OCOOEt, and OCON(Me)(2) reduced the activity. In the same replacement at C-9 (ring D), the activity depended upon the type of the oxygen function. Six protoberberines displayed more potent activity than berberine 1. The activity decreased in the order: 10, 11, 17 and 18 > 7 and 8 > 1. (C) 1999 Editions scientifiques et medicales Elsevier SAS.