9,10-dimethoxy-13-(2-naphthylmethyleneoxy)-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium bromide | 1160707-15-2

• 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: 9,10-dimethoxy-13-(2-naphthylmethyleneoxy)-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium bromide
• 英文别名: 16,17-Dimethoxy-21-(naphthalen-2-ylmethoxy)-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;bromide
• CAS: 1160707-15-2
• 化学式: Br*C₃₁H₂₆NO₅
• 分子量: 572.455
• InChiKey: CHTKXPLNFCWLNA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  50
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  berberinephenolbetaine 、 2-溴甲基萘 以 乙腈 为溶剂， 以34%的产率得到9,10-dimethoxy-13-(2-naphthylmethyleneoxy)-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium bromide
  参考文献：
  名称：

  Antibacterial activity of berberine-NorA pump inhibitor hybrids with a methylene ether linking group

  摘要：

  Conjugation of the NorA substrate berberine and the NorA inhibitor 5-nitro-2-phenyl-1H-indole via a methylene ether linking group gave the 13-substituted berberine-NorA inhibitor hybrid, 3. A series of simpler arylmethyl ether hybrid structures were also synthesized. The hybrid 3 showed excellent antibacterial activity (MIC Staphylococcus aureus, 1.7 mu M), which was over 382-fold more active than the parent antibacterial berberine, against this bacterium. This compound was also shown to block the NorA efflux pump in S. aureus. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.028

文献信息

• Antibacterial activity of berberine-NorA pump inhibitor hybrids with a methylene ether linking group
  作者：Siritron Samosorn、Bongkot Tanwirat、Nussara Muhamad、Gabriele Casadei、Danuta Tomkiewicz、Kim Lewis、Apichart Suksamrarn、Therdsak Prammananan、Karina C. Gornall、Jennifer L. Beck、John B. Bremner

  DOI：10.1016/j.bmc.2009.04.028

  日期：2009.6

  Conjugation of the NorA substrate berberine and the NorA inhibitor 5-nitro-2-phenyl-1H-indole via a methylene ether linking group gave the 13-substituted berberine-NorA inhibitor hybrid, 3. A series of simpler arylmethyl ether hybrid structures were also synthesized. The hybrid 3 showed excellent antibacterial activity (MIC Staphylococcus aureus, 1.7 mu M), which was over 382-fold more active than the parent antibacterial berberine, against this bacterium. This compound was also shown to block the NorA efflux pump in S. aureus. (C) 2009 Elsevier Ltd. All rights reserved.