4-O-[2"-O-[7-[4-hydroxypiperidin-1-yl]heptyl]-3",4"-di-O-methyl-β-D-xylopyranosyl]diphyllin

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素苷
• 英文名称: 4-O-[2"-O-[7-[4-hydroxypiperidin-1-yl]heptyl]-3",4"-di-O-methyl-β-D-xylopyranosyl]diphyllin
• 英文别名: 9-(1,3-benzodioxol-5-yl)-4-[(2S,3R,4S,5R)-3-[7-(4-hydroxypiperidin-1-yl)heptoxy]-4,5-dimethoxyoxan-2-yl]oxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one
• 化学式: C₄₀H₅₁NO₁₂
• 分子量: 737.844
• InChiKey: AHKASPSPLYXDJZ-MTZNQXOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  53
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  1,7-二溴庚烷 在 sodium hydroxide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-O-[2"-O-[7-[4-hydroxypiperidin-1-yl]heptyl]-3",4"-di-O-methyl-β-D-xylopyranosyl]diphyllin
  参考文献：
  名称：

  Synthesis and bioevaluation of heterocyclic derivatives of Cleistanthin-A

  摘要：

  The vacuolar H+-ATPase (V-ATPase) was proposed as a key target for new strategies in cancer treatment recently. We have synthesized a novel class of derivatives of Cleistanthin-A bearing heterocyclic moieties. Most of these compounds displayed potent antiproliferative effects on four cancer cells at submicromolar concentration, and they have no cytotoxicity on normal WRL-68 cells at 200 nM. The most potent compound 3a has been shown to inhibit the activity of vacuolar H+-ATPase at submicromolar concentration, and it could also significantly decrease the cytosolic pH values in HepG2 cells. The current findings provide valuable insights for future development of novel V-ATPase inhibitors as anticancer agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.033

文献信息

• Synthesis and bioevaluation of heterocyclic derivatives of Cleistanthin-A
  作者：Yu Zhao、Rui Zhang、Yapeng Lu、Jinlong Ma、Li Zhu

  DOI：10.1016/j.bmc.2015.05.033

  日期：2015.8

  The vacuolar H+-ATPase (V-ATPase) was proposed as a key target for new strategies in cancer treatment recently. We have synthesized a novel class of derivatives of Cleistanthin-A bearing heterocyclic moieties. Most of these compounds displayed potent antiproliferative effects on four cancer cells at submicromolar concentration, and they have no cytotoxicity on normal WRL-68 cells at 200 nM. The most potent compound 3a has been shown to inhibit the activity of vacuolar H+-ATPase at submicromolar concentration, and it could also significantly decrease the cytosolic pH values in HepG2 cells. The current findings provide valuable insights for future development of novel V-ATPase inhibitors as anticancer agents. (C) 2015 Elsevier Ltd. All rights reserved.