9-N,N-Dimethylcarbamoyl, 9-demethylberberine chloride | 54312-78-6

• 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: 9-N,N-Dimethylcarbamoyl, 9-demethylberberine chloride
• 英文别名: (17-methoxy-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-16-yl) N,N-dimethylcarbamate;chloride
• CAS: 54312-78-6
• 化学式: C₂₂H₂₁N₂O₅*Cl
• 分子量: 428.872
• InChiKey: ACMCHMAHFWXGEV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  10-甲氧基-5,6-二氢苯并[g]-1,3-苯并二氧戊环并[5,6-a]喹嗪鎓-9-醇 、 二甲氨基甲酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 以82%的产率得到9-N,N-Dimethylcarbamoyl, 9-demethylberberine 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

• 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.