17-Methoxy-21-[(4-propan-2-ylphenyl)methyl]-16-[(3,4,5-trifluorophenyl)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;chloride | 1257844-25-9

• 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: 17-Methoxy-21-[(4-propan-2-ylphenyl)methyl]-16-[(3,4,5-trifluorophenyl)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;chloride
• CAS: 1257844-25-9
• 化学式: C₃₆H₃₁F₃NO₄*Cl
• 分子量: 634.095
• InChiKey: ZGVIXFCJNMVBMX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  45
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  13-(4-isopropylbenzyl)-10-methoxy-9-((3,4,5-trifluorobenzyl)oxy)-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium bromide 在 silver(I) chloride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 17-Methoxy-21-[(4-propan-2-ylphenyl)methyl]-16-[(3,4,5-trifluorophenyl)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;chloride
  参考文献：
  名称：

  Synthesis and antifungal activity of a novel series of 13-(4-isopropylbenzyl)berberine derivatives

  摘要：

  By replacing the methyl group of 13-(4-isopropylbenzyl)berberine 2 with various acyl, alkyl, and benzyl groups via the demethylated intermediate, 13-(4-isopropylbenzyl) berberrubine 4, a novel series of 9-O-alkyl-13-(4-isopropylbenzyl)berberine derivatives was synthesized and examined for antifungal activities against various human pathogenic fungi. The introduction of various alkyl groups led to enhanced antifungal activity but that of acyl groups resulted in decrease of the activity. Among them, 9-O-butyl-13-(4-isopropylbenzyl)berberine 6d exhibited the most potent antifungal activities against Cryptococcus neoformans, Candida species (MIC = 0.25-1 mu g/ml), and Aspergillus species (MIC = 2-4 mu g/ml). The compound was found to be relatively safe up to 900 mg/kg in oral administration to mice. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.045