13-Ethylberberine iodide | 38969-42-5

• 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-Ethylberberine iodide
• 英文别名: 13-ethyl-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolinylium; iodide；13-ethyl-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium iodide；13-Aethyl-berberinium-jodid；13-Ethylberberiniumiodid；Ethylberberinium-jodid；13-Aethylberberinium；21-Ethyl-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;iodide
• CAS: 38969-42-5
• 化学式: C₂₂H₂₂NO₄*I
• 分子量: 491.325
• InChiKey: KSEFVVNXFFBBBG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  13-Ethylberberine iodide 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 生成 13-ethyl-9-hydroxy-10-methoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium iodide
  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
• 作为产物：
  描述：

  丙酮小檗碱 、 碘乙烷 反应 5.0h， 以45.7%的产率得到13-Ethylberberine iodide
  参考文献：
  名称：

  NOVEL ISOQUINOLINE DERIVATIVES

  摘要：

  这项发明提供了式（I）的新化合物或其药用可接受盐，其中R1至R7如本文所述，包括这些化合物的组合物以及制备和使用这些化合物的方法。

  公开号：

  US20100286396A1

文献信息

• [EN] NOVEL ISOQUINOLINE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'ISOQUINOLÉINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2010128061A1

  公开（公告）日：2010-11-11

  A compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R1 to R7 have the significance given in claim 1, can be used in the form of a pharmaceutical composition.

  化合物的结构式（I）或其药学上可接受的盐，其中R1至R7具有权利要求书中给定的含义，可用作药物组合物的形式。
• Syntheses and absorption spectra of some compounds with the berbine structure
  作者：S. Pavelka、J. Kovář

  DOI：10.1135/cccc19763654

  日期：——
• Antibacterial activity and structure-activity relationships of berberine analogs
  作者：K Iwasa、M Kamigauchi、M Ueki、M Taniguchi

  DOI：10.1016/0223-5234(96)85167-1

  日期：1996.1

  Analogs of berberine 1 and related compounds were prepared to evaluate structure-activity relationships. Among the 13-alkyl-substituted and the 13-unsubstituted protoberberinium salts, the 13-ethyl-9-ethoxyl homolog 30, the 13-ethyl analog 29, and the 13-methyl derivative 3 showed an increase in antibacterial activity against Staphylococcus aureus by eight-, four- and twofold respectively over the parent base berberine 1; this is suggestive that steric effects play a significant role in the antibacterial. activity. Reduction of the protoberberinium salts yielding the tetrahydro derivatives greatly reduced the antibacterial activity. Replacement of methoxyl groups at the C-2 and the C-3 of ring A by a methylenedioxy group resulted in increased antibacterial activity. These data strongly suggest that the quaternary nitrogen atom such as in protoberberinium salts, an alkylsubstituent at C-13, and a methylenedioxy function at C-2 and C-3 are required for enhanced activity. Tetrahydroprotoberberine alpha-N-metho salts showed higher activity than tetrahydroprotoberberine hydrochlorides, but appreciably lower activity than protoberberinium salts. The effects of substitution at C-13 and on ring A in the alpha-N-metho salt were similar to those in protoberberinium salts. Stereochemical changes of the B/C ring juncture from trans to cis, and of the methyl group at C-13 from alpha to beta, had, respectively, marked and slight effects on the activity. The tested compounds were less active against Escherichia coli (Gram-negative bacterium) and Candida albicans (fungus) than S aureus (Gram-positive bacterium).