2-methoxy-3,8,9-trihydroxy coumestan

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 2-methoxy-3,8,9-trihydroxy coumestan
• 英文别名: PCALC36；3,8,9-Trihydroxy-2-methoxy-benzofuro[3,2-c]chromen-6-one；3,8,9-trihydroxy-2-methoxy-[1]benzofuro[3,2-c]chromen-6-one
• 化学式: C₁₆H₁₀O₇
• 分子量: 314.251
• InChiKey: BPUFWAUISSHYSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-苄氧基-4-甲氧基苯甲醛 在 palladium on activated charcoal 、 palladium dichloride 盐酸 、 氢氧化钾 、 氢气 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 84.0h， 生成 2-methoxy-3,8,9-trihydroxy coumestan
  参考文献：
  名称：

  Structure–activity relationship of wedelolactone analogues: Structural requirements for inhibition of Na+,K+-ATPase and binding to the central benzodiazepine receptor

  摘要：

  Coumestans 2a-i, bearing different patterns of substitution in A- and D-rings, were synthesized and evaluated as inhibitors of kidney Na+, K+ -ATPase and ligands for the central benzodiazepine (BZP) receptor. The presence of a hydroxyl group in position 2 favours the effect on Na+, K+ -ATPase but decreases the affinity for the BZP receptor, allowing the design of more selective molecules than the natural wedelolactone. On the other hand, the presence of a catechol in ring D is important for the effect on both molecular targets.

  DOI：

  10.1016/j.bmc.2006.07.053

文献信息

• Structure–activity relationship of wedelolactone analogues: Structural requirements for inhibition of Na+,K+-ATPase and binding to the central benzodiazepine receptor
  作者：Elisa S.C. Pôças、Daniele V.S. Lopes、Alcides J.M. da Silva、Paulo H.C. Pimenta、Fernanda B. Leitão、Chaquip D. Netto、Camilla D. Buarque、Flávia V. Brito、Paulo R.R. Costa、François Noël

  DOI：10.1016/j.bmc.2006.07.053

  日期：2006.12

  Coumestans 2a-i, bearing different patterns of substitution in A- and D-rings, were synthesized and evaluated as inhibitors of kidney Na+, K+ -ATPase and ligands for the central benzodiazepine (BZP) receptor. The presence of a hydroxyl group in position 2 favours the effect on Na+, K+ -ATPase but decreases the affinity for the BZP receptor, allowing the design of more selective molecules than the natural wedelolactone. On the other hand, the presence of a catechol in ring D is important for the effect on both molecular targets.