3,4-dihydroxy-2-(hydroxymethyl)-8,10-diisopropoxy-9-methoxy-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen-6(10bH)-one | 1373401-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 3,4-dihydroxy-2-(hydroxymethyl)-8,10-diisopropoxy-9-methoxy-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen-6(10bH)-one
• 英文别名: (2R,3S,4S,4aR,10bS)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-8,10-di(propan-2-yloxy)-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
• CAS: 1373401-99-0
• 化学式: C₂₀H₂₈O₉
• 分子量: 412.437
• InChiKey: AXLFOSKKQLXHLN-UMILVCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3,4-dihydroxy-2-(hydroxymethyl)-8,10-diisopropoxy-9-methoxy-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen-6(10bH)-one
  参考文献：
  名称：

  Synthesis of new bergenin derivatives as potent inhibitors of inflammatory mediators NO and TNF-α

  摘要：

  Bergenin is an isocoumarin natural product which aides in fat loss, healthy weight maintenance, enhancing the lipolytic effects of norepinephrine, inhibiting the formation of interleukin 1 alpha and cyclooxygenases-2. Here we describe the anti-inflammatory activity of new bergenin derivatives 1-15 in the respiratory burst assay. Bergenin was isolated from the crude extract of Mallotus philippenensis after repeated column chromatography and was then subjected to chemical derivatization. The structures of all compounds were elucidated by NMR and mass spectroscopic techniques. Compound 2 was also studied using single crystal X-ray diffraction. Compounds 4, (54.5 +/- 2.2%) 5 (47.5 +/- 0.5%) 5, and 15 (86.8 +/- 1.9%) showed significant (P <= 0.005) NO inhibitory activities whereas 6, 7, 11, 12 and 13 displayed moderate inhibitory activities that ranges between 16% and 31%. Furthermore compounds 4 and 15, were discovered as significant (P <= 0.005) TNF-alpha inhibitors with 98% and 96% inhibition, respectively, while compounds 3, 5, 7, 8, 11, and 12 showed low level of TNF-alpha inhibition (0.4-28%). Compounds 8, 13 and 15 exhibited moderate anti-inflammatory IC50 activities with 212, 222, and 253 mu M, respectively, compared to the standard anti-inflammatory drug indomethacin as well as the parent bergenin compound. No cytotoxic effects could be detected when the compounds were tested on 3T3 cells up to concentrations of 100 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.096