1,3,6-trihydroxy-2,4-bis(2-hydroxynaphthalen-1-yl)-9H-xanthen-9-one | 1335200-38-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1,3,6-trihydroxy-2,4-bis(2-hydroxynaphthalen-1-yl)-9H-xanthen-9-one
• 英文别名: 1,3,6-Trihydroxy-2,4-bis(2-hydroxynaphthalen-1-yl)xanthen-9-one
• CAS: 1335200-38-8
• 化学式: C₃₃H₂₀O₇
• 分子量: 528.518
• InChiKey: KSIMGQLBHZWLOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  40
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  gentisein 、 2-萘酚 在 copper(II) choride dihydrate 、 四甲基乙二胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以30%的产率得到1,3,6-trihydroxy-2,4-bis(2-hydroxynaphthalen-1-yl)-9H-xanthen-9-one
  参考文献：
  名称：

  Toward potent α-glucosidase inhibitors based on xanthones: A closer look into the structure–activity correlations

  摘要：

  A series of novel xanthone derivatives 6-16 having non-coplanar and flexible structures were synthesized as potent alpha-glucosidase inhibitors. Biological evaluation indicated that compounds 6-12 bearing one or two naphthol moieties exhibited up to 30-fold enhanced activities compared with their corresponding parent compounds 2-5, whereas compounds 13-16 bearing one dihydroxylnaphthalenyl group showed decreased activities compared with their corresponding analogs 6-9 having one naphthol group. Among them, compounds 7-8, 10-12 and 15 were more active than 1-deoxynojirimycin, a well-known inhibitor for alpha-glucosidase. The structure-activity correlations suggested that inhibiting of alpha-glucosidase was a result of multiple interactions with the enzyme, including pi-stacking, hydrophobic effect and conformational flexibility due to the structural non-coplanarity. In addition, compounds 4, 8 and 15 showed non-competitive inhibition. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.003

文献信息

• Toward potent α-glucosidase inhibitors based on xanthones: A closer look into the structure–activity correlations
  作者：Gai-Li Li、Jia-Yun He、Aiqin Zhang、Yiqian Wan、Bo Wang、Wen-Hua Chen

  DOI：10.1016/j.ejmech.2011.06.003

  日期：2011.9

  A series of novel xanthone derivatives 6-16 having non-coplanar and flexible structures were synthesized as potent alpha-glucosidase inhibitors. Biological evaluation indicated that compounds 6-12 bearing one or two naphthol moieties exhibited up to 30-fold enhanced activities compared with their corresponding parent compounds 2-5, whereas compounds 13-16 bearing one dihydroxylnaphthalenyl group showed decreased activities compared with their corresponding analogs 6-9 having one naphthol group. Among them, compounds 7-8, 10-12 and 15 were more active than 1-deoxynojirimycin, a well-known inhibitor for alpha-glucosidase. The structure-activity correlations suggested that inhibiting of alpha-glucosidase was a result of multiple interactions with the enzyme, including pi-stacking, hydrophobic effect and conformational flexibility due to the structural non-coplanarity. In addition, compounds 4, 8 and 15 showed non-competitive inhibition. (C) 2011 Elsevier Masson SAS. All rights reserved.