21-[(3,5-Dimethoxyphenyl)methyl]-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-octaene;chloride | 1132842-12-6

• 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: 21-[(3,5-Dimethoxyphenyl)methyl]-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-octaene;chloride
• CAS: 1132842-12-6
• 化学式: C₂₉H₂₈NO₆*Cl
• 分子量: 521.997
• InChiKey: BWSIJTDBBMJDQC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,5-二甲氧基苄基氯 、 丙酮小檗碱 以 乙腈 为溶剂， 生成 21-[(3,5-Dimethoxyphenyl)methyl]-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-octaene;chloride
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel, substituted 5,6-dihydrodibenzo[a,g]quinolizinium P2X7 antagonists

  摘要：

  Iminium quaternary protoberberine alkaloids (QPA) have been found to be novel P2X(7) antagonists. To assess their structure-activity relationships, these compounds were modified at their R-1 and R-2 groups and assayed for their ability to inhibit the 2'(3')-O-(4-benzoylbenzoyl)-ATP (BzATP)-induced uptake of fluorescent ethidium by HEK-293 cells stably expressing the human P2X(7) receptor, and their ability to inhibit BzATP-induced IL-1 beta release by differentiated THP-1 cells. Compounds 15a and 15d, with alkyl groups at the R-1 position, and especially compound 19h, with the 2-NO2-4,5-dimethoxy-benzyl group at the R-2 position, had potent inhibitory efficacy as P2X(7) antagonists. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.088

文献信息

• Synthesis and structure–activity relationships of novel, substituted 5,6-dihydrodibenzo[a,g]quinolizinium P2X7 antagonists
  作者：Ga Eun Lee、Ho-Sung Lee、So Deok Lee、Jung-Ho Kim、Won-Ki Kim、Yong-Chul Kim

  DOI：10.1016/j.bmcl.2008.11.088

  日期：2009.2

  Iminium quaternary protoberberine alkaloids (QPA) have been found to be novel P2X(7) antagonists. To assess their structure-activity relationships, these compounds were modified at their R-1 and R-2 groups and assayed for their ability to inhibit the 2'(3')-O-(4-benzoylbenzoyl)-ATP (BzATP)-induced uptake of fluorescent ethidium by HEK-293 cells stably expressing the human P2X(7) receptor, and their ability to inhibit BzATP-induced IL-1 beta release by differentiated THP-1 cells. Compounds 15a and 15d, with alkyl groups at the R-1 position, and especially compound 19h, with the 2-NO2-4,5-dimethoxy-benzyl group at the R-2 position, had potent inhibitory efficacy as P2X(7) antagonists. (C) 2008 Elsevier Ltd. All rights reserved.