6,7-bis(phenylmethoxy)-2H-chromene | 916754-90-0

• 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: 6,7-bis(phenylmethoxy)-2H-chromene
• CAS: 916754-90-0
• 化学式: C₂₃H₂₀O₃
• 分子量: 344.41
• InChiKey: XMTAMLDWJMBKAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-bis(phenylmethoxy)-2H-chromene 在 palladium on activated charcoal 、 palladium dichloride 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium chloride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 20.0~25.0 ℃ 、303.98 kPa 条件下， 反应 30.0h， 生成 15,16-Dihydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-1(12),2,4(8),9,13,15,17-heptaen-20-one
  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
• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 在 盐酸 、 氢氧化钾 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 54.0h， 生成 6,7-bis(phenylmethoxy)-2H-chromene
  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

• (±)-3,4-Dihydroxy-8,9-methylenedioxypterocarpan and derivatives: Cytotoxic effect on human leukemia cell lines
  作者：Chaquip D. Netto、Eduardo S.J. Santos、Carolina Pereira Castro、Alcides J.M. da Silva、Vivian M. Rumjanek、Paulo R.R. Costa

  DOI：10.1016/j.ejmech.2008.01.027

  日期：2009.2

  Naturally occurring pterocarpans 1a,b, pterocarpan 1c, isoflavane 2 and ortho-quinone 3 were synthesized in the racemic form and their totoxic effect was evaluated on the human leukemia cell lines K562 (resistant to oxidative stress), Lucena-1 (MDR phenotype) and Ortho-quinone 3 (IC50 = 1.5 mu M, 1.8 mu M and 0.2 mu M, respectively) and catechol pterocarpan 1a (IC50 = 3.0 mu M, 3.7 mu M and 2.1 mu M, respectively) were the most active compounds on these cells and were also evaluated on other human leukemia cell lines (Jurkat and Daudi). quinone 3 was 2 to 10 times more potent than pterocarpan 1a, depending on the cell line considered, however, showed a greater toxicity lymphocytes activated by PHA. (C) 2008 Published by Elsevier Masson SAS.
• 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.