Acetic acid 9-methoxy-8-oxo-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-10-yl ester

• 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: Acetic acid 9-methoxy-8-oxo-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-10-yl ester
• 英文别名: Acetyl 8-oxotetrahydrothalifendine；(16-methoxy-14-oxo-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-17-yl) acetate
• 化学式: C₂₁H₁₉NO₆
• 分子量: 381.385
• InChiKey: DMUHZKPEYXYPKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酸酐 、 8-Oxotetrahydrothalifendine 在 吡啶 作用下， 以 吡啶 为溶剂， 以12 mg的产率得到Acetic acid 9-methoxy-8-oxo-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-10-yl ester
  参考文献：
  名称：

  Antitubercular Natural Products:  Berberine from the Roots of Commercial Hydrastis canadensis Powder. Isolation of Inactive 8-Oxotetrahydrothalifendine, Canadine, β-Hydrastine, and Two New Quinic Acid Esters, Hycandinic Acid Esters-1 and -2

  摘要：

  Berberine (4) is responsible for the activity of an extract of a commercial root sample of Hydrastis canadensis against multiply drug resistant Mycobacteriun tuberculosis. Two new quinic acid feruloyl esters, compounds 2 and 3, have been isolated from the same source along with canadine (1c), 8-oxotetrahydrothalifendine (1), and beta-hydrastine (5). These were found to be inactive. The structures of the new compounds were elucidated from spectral (H-1, C-13, HMQC, HMBC, and H-H COSY) and chemical evidences.

  DOI：

  10.1021/np9701889

文献信息

• Antitubercular Natural Products:  Berberine from the Roots of Commercial <i>Hydrastis </i><i>c</i><i>anadensis </i>Powder. Isolation of Inactive 8-Oxotetrahydrothalifendine, Canadine, β-Hydrastine, and Two New Quinic Acid Esters, Hycandinic Acid Esters-1 and -2
  作者：Elmer J. Gentry、Hanuman B. Jampani、Ali Keshavarz-Shokri、Martha D. Morton、David Vander Velde、Hanumaiah Telikepalli、Lester A. Mitscher、Ribhi Shawar、Debbi Humble、William Baker

  DOI：10.1021/np9701889

  日期：1998.10.1

  Berberine (4) is responsible for the activity of an extract of a commercial root sample of Hydrastis canadensis against multiply drug resistant Mycobacteriun tuberculosis. Two new quinic acid feruloyl esters, compounds 2 and 3, have been isolated from the same source along with canadine (1c), 8-oxotetrahydrothalifendine (1), and beta-hydrastine (5). These were found to be inactive. The structures of the new compounds were elucidated from spectral (H-1, C-13, HMQC, HMBC, and H-H COSY) and chemical evidences.