13-(4-isopropylbenzyl)-9-O-(4-isopropylbenzyl)berberrubine chloride | 946576-38-1

• 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-(4-isopropylbenzyl)-9-O-(4-isopropylbenzyl)berberrubine chloride
• 英文别名: 17-Methoxy-16-[(4-propan-2-ylphenyl)methoxy]-21-[(4-propan-2-ylphenyl)methyl]-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: 946576-38-1
• 化学式: C₃₉H₄₀NO₄*Cl
• 分子量: 622.204
• InChiKey: XLKCYELBGPBROE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  13-(4-isopropylbenzyl)-9-O-(4-isopropylbenzyl)berberrubine bromide 在 silver(I) chloride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 13-(4-isopropylbenzyl)-9-O-(4-isopropylbenzyl)berberrubine chloride
  参考文献：
  名称：

  Berberrubine Derivatives Having Antifungal Activities

  摘要：

  本发明涉及一种具有优越抗真菌活性的小檗碱衍生物，更具体地说，涉及一种对壳聚糖合酶具有抑制活性的小檗碱衍生物，该酶参与壳聚糖的合成，在真菌生长中是必不可少的，并且对人类致病真菌具有强大的抗真菌活性。

  公开号：

  US20100292476A1

文献信息

• Berberrubine Derivatives Having Antifungal Activities
  申请人：Kim Sung Uk

  公开号：US20100292476A1

  公开（公告）日：2010-11-18

  The present invention relates to a berberrubine derivative having superior antifungal activity, more particularly to a berberrubine derivative having inhibitory activity against chitin synthase, which participates in the synthesis of chitin and is essential in the growth of fungi, and having a potent antifungal activity against human pathogenic fungi.

  本发明涉及一种具有优越抗真菌活性的小檗碱衍生物，更具体地说，涉及一种对壳聚糖合酶具有抑制活性的小檗碱衍生物，该酶参与壳聚糖的合成，在真菌生长中是必不可少的，并且对人类致病真菌具有强大的抗真菌活性。
• Synthesis and antifungal activity of a novel series of 13-(4-isopropylbenzyl)berberine derivatives
  作者：Ki Duk Park、Sung Jin Cho、Jae Sun Moon、Sung Uk Kim

  DOI：10.1016/j.bmcl.2010.09.045

  日期：2010.11

  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.