9,10-dimethoxy-6,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline hydrochloride | 86933-66-6

• 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-6,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline hydrochloride
• 英文别名: berberine hydrochloride；dihydroberberine hydrochloride；9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline; hydrochloride；9,10-Dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isochino[3,2-a]isochinolin; Hydrochlorid；16,17-Dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaene;hydrochloride
• CAS: 86933-66-6
• 化学式: C₂₀H₁₉NO₄*ClH
• 分子量: 373.836
• InChiKey: ZLKNVOLRJPXHFR-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  9,10-dimethoxy-6,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline hydrochloride 在 吡啶 、 sodium tetrahydroborate 作用下， 以80.1 %的产率得到二氢小檗碱
  参考文献：
  名称：

  基于水凝胶的宏观点击化学

  摘要：

  点击化学通常用于在微观水平上连接组件，但不适合连接宏观构件。由宏观积木组成的材料实现了宏观层面三维结构的柔性制造，对于并行制造具有重要意义。在这里，宏观点击化学是使用水凝胶作为宏观构建块实现的。

  DOI：

  10.1002/anie.202315086
• 作为产物：
  描述：

  胡椒乙胺 在 甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 30.67h， 生成 9,10-dimethoxy-6,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline hydrochloride
  参考文献：
  名称：

  电化学无受体脱氢高效环保合成原小檗碱和 13-Me 原小檗碱生物碱

  摘要：

  天然产物电合成：用于合成原小檗碱和 13-Me 原小檗碱生物碱的环保方案依赖于最后阶段的电化学无受体脱氢，在温和的反应条件下在室温下使用 10 mol% I 2 作为氧化还原介质。

  DOI：

  10.1002/cctc.202201553

文献信息

• Antimicrobial Activity of 8-Alkyl- and 8-Phenyl-Substituted Berberines and Their 12-Bromo Derivatives
  作者：Kinuko Iwasa、Dong-Ung Lee、So-Im Kang、Wolfgang Wiegrebe

  DOI：10.1021/np980044+

  日期：1998.9.1

  The 8-alkyl- (3-6), 8-phenyl- (7), 12-bromo- (8), 8-alkyl-12-bromo- (9-12), and 12-bromo-8-phenyl- (13) berberine derivatives were prepared and tested for their antimicrobial activity in vitro to evaluate structure-activity relationships. Introduction of the alkyl or phenyl group and the bromine atom into the C-8 and C-12 positions of berberine (1), respectively, led to significant increases of the antimicrobial activity. In both the 8-alkyl- and 8-alkyl-12-bromoberberines (3-6 and 9-12, respectively), the antibacterial activity increased as the length of the aliphatic chain increased. The exception was the activity against Candida albicans and Escherichia coli, which did not always increase as the alkyl side chain lengthened. Among the compounds tested, 12-bromo-8-n-hexylberberine (12) was 64, 256, 128, 16, and 32 times more active against Staphylococcus aureus, Bacillus subtilis, Salmonella enteritidis, E. coli, and C. albicans, respectively, in comparison to the clinically used berberine. Compound 12 was also found to be 8, 16, and 128 times more active against S. aureus, S. enteritidis, and C. albicans, respectively, than kanamycin sulfate, but was of the same order of activity against B. subtilis, and only one-fourth as active against E. coli.