(4bR,8aS,9S)-1-(3,4-dihydroxyphenyl)-4-hydroxy-3,7-dimethoxy-11-methyl-9,10-dihydro-5H-9,4b-(epiminoethano)phenanthren-6(8aH)-one | 1067650-94-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: (4bR,8aS,9S)-1-(3,4-dihydroxyphenyl)-4-hydroxy-3,7-dimethoxy-11-methyl-9,10-dihydro-5H-9,4b-(epiminoethano)phenanthren-6(8aH)-one
• CAS: 1067650-94-5
• 化学式: C₂₅H₂₇NO₆
• 分子量: 437.492
• InChiKey: FCHSOZWISKADOL-LEHBWIKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  99.46
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  邻苯二酚 、 青藤碱 在 Coriolus unicolor 作用下， 反应 24.0h， 以18%的产率得到(4bR,8aS,9S)-1-(3,4-dihydroxyphenyl)-4-hydroxy-3,7-dimethoxy-11-methyl-9,10-dihydro-5H-9,4b-(epiminoethano)phenanthren-6(8aH)-one
  参考文献：
  名称：

  Biocatalyzed cross-coupling of sinomenine and 1,2-dihydroxybenzene by Coriolus unicolor

  摘要：

  Sinomenine is a clinically available drug for the treatment of rheumatoid arthritis (RA). In a continuous research aiming at discovery of sinomenine derivates with better bioactivity, a cross-coupling reaction of sinomenine and 1,2-dihydroxybenzene catalyzed by a fungus Coriolus unicolor afforded an unique C C cross-coupled compound 2, together with (S)-disinomenine and (R)-disinomenine. The structure of 2 was elucidated by MS and NMR spectroscopy. Compound 2 was further assayed for the inhibitory activity on IL-6 overproduction in SW982 cells and exhibited a much more potent activity on IL-6 (96% inhibition) compared with those of (S)-disinomenine and sinomenine (17% and 12% inhibition, respectively). (C) 2012 Zhang Shuang Deng. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.01.004