9-O-ethylberberrubine iodide | 62595-70-4

• 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-O-ethylberberrubine iodide
• 英文别名: 9-Demethoxy-9-aethoxy-berberinium；9-ethoxy-10-methoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolinylium; iodide；9-Aethoxy-10-methoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isochino[3,2-a]isochinolinylium; Jodid；16-Ethoxy-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-octaene;iodide
• CAS: 62595-70-4
• 化学式: C₂₁H₂₀NO₄*I
• 分子量: 477.299
• InChiKey: TTYDBSCMXVCEFB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.49
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  盐酸小檗碱 以 N,N-二甲基甲酰胺 为溶剂， 120.0~190.0 ℃ 、4.0 kPa 条件下， 反应 5.25h， 生成 9-O-ethylberberrubine iodide
  参考文献：
  名称：

  Antibacterial activity and structure-activity relationships of berberine analogs

  摘要：

  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).

  DOI：

  10.1016/0223-5234(96)85167-1

文献信息

• Frerichs; Stoepel, Archiv der Pharmazie, 1913, vol. 251, p. 329
  作者：Frerichs、Stoepel

  DOI：——

  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).