Ra-6,7-dihydro-6-(1'-hydroxyethyl)-3,9-dimethoxy-6-methyl-5H-dibenzo[a,c]cycloheptene-1,2,10,11-tetraol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: Ra-6,7-dihydro-6-(1'-hydroxyethyl)-3,9-dimethoxy-6-methyl-5H-dibenzo[a,c]cycloheptene-1,2,10,11-tetraol
• 英文别名: 9-(1-Hydroxyethyl)-5,13-dimethoxy-9-methyltricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaene-3,4,14,15-tetrol
• 化学式: C₂₀H₂₄O₇
• 分子量: 376.406
• InChiKey: ZFQNFMQTEKLASN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  schizandrin 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到Ra-6,7-dihydro-6-(1'-hydroxyethyl)-3,9-dimethoxy-6-methyl-5H-dibenzo[a,c]cycloheptene-1,2,10,11-tetraol
  参考文献：
  名称：

  Derivatives of schisandrin with increased inhibitory potential on prostaglandin E2 and leukotriene B4 formation in vitro

  摘要：

  Four derivatives of schisandrin, a major dibenzo[a,c]cyclooctadiene lignan of Schisandra chinensis (Turcz.) Baillon were synthesized and structurally characterized by means of NMR and mass spectroscopy. Furthermore, axial chirality of the biphenyl system was determined by comparison of calculated with measured circular dichroism (CD) spectra. Three of the obtained derivatives showed a ring contraction during chemical modification. While the original lignans were inactive on the performed bioassays, the compounds which showed the cycloheptadiene skeleton revealed remarkable activities. For the inhibition of LTB4 production the IC50 values of aR-6,7-dihydro-6-(1'-hydroxyethyl)-3,9-dimethoxy-6-methyl-5H-dibenzo[a,c]cycloheptene-1,2,10,11-tetraol (6) and aR-6-(1'-iodoethyl)-1,2,3,9,10,11-hexamethoxy-6-methyl-5H-dibenzo[a,c]cycloheptene (8) were 4.2 +/- 0.3 mu M and 4.5 +/- 0.2 mu M, respectively. aR-6,7-Dihydro-6-(10-hydroxyethyl)-6-methyl-5H-dibenzo[a,c]cycloheptene-1,2,3,9,10,11-hexaol (5) revealed dual inhibition on COX-2 (IC50 32.1 +/- 2.5 mu M) and on LTB4 production (37.3 +/- 5.5% inhibition at 50 mu M). (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.10.031

文献信息

• Derivatives of schisandrin with increased inhibitory potential on prostaglandin E2 and leukotriene B4 formation in vitro
  作者：Martina Blunder、Eva M. Pferschy-Wenzig、Walter M.F. Fabian、Antje Hüfner、Olaf Kunert、Robert Saf、Wolfgang Schühly、Rudolf Bauer

  DOI：10.1016/j.bmc.2009.10.031

  日期：2010.4

  Four derivatives of schisandrin, a major dibenzo[a,c]cyclooctadiene lignan of Schisandra chinensis (Turcz.) Baillon were synthesized and structurally characterized by means of NMR and mass spectroscopy. Furthermore, axial chirality of the biphenyl system was determined by comparison of calculated with measured circular dichroism (CD) spectra. Three of the obtained derivatives showed a ring contraction during chemical modification. While the original lignans were inactive on the performed bioassays, the compounds which showed the cycloheptadiene skeleton revealed remarkable activities. For the inhibition of LTB4 production the IC50 values of aR-6,7-dihydro-6-(1'-hydroxyethyl)-3,9-dimethoxy-6-methyl-5H-dibenzo[a,c]cycloheptene-1,2,10,11-tetraol (6) and aR-6-(1'-iodoethyl)-1,2,3,9,10,11-hexamethoxy-6-methyl-5H-dibenzo[a,c]cycloheptene (8) were 4.2 +/- 0.3 mu M and 4.5 +/- 0.2 mu M, respectively. aR-6,7-Dihydro-6-(10-hydroxyethyl)-6-methyl-5H-dibenzo[a,c]cycloheptene-1,2,3,9,10,11-hexaol (5) revealed dual inhibition on COX-2 (IC50 32.1 +/- 2.5 mu M) and on LTB4 production (37.3 +/- 5.5% inhibition at 50 mu M). (C) 2010 Published by Elsevier Ltd.