5-Hydroxy-1,2-dihydro-benzo[f]chromen-3-one | 667456-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 5-Hydroxy-1,2-dihydro-benzo[f]chromen-3-one
• 英文别名: 5-hydroxy-1,2-dihydrobenzo[f]chromen-3-one
• CAS: 667456-63-5
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: BKBHSAUUJWRKEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 5-Hydroxy-1,2-dihydro-benzo[f]chromen-3-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以94%的产率得到5-Benzyloxy-1,2-dihydro-benzo[f]chromen-3-one
  参考文献：
  名称：

  Inhibitors of Sir2:  Evaluation of Splitomicin Analogues

  摘要：

  Splitomicin (1) and 41 analogues were prepared and evaluated in cell-based Sir2 inhibition and toxicity assays and an in vitro Sir2 inhibition assay. Lactone ring or naphthalene (positions 7-9) substituents decrease activity, but other naphthalene substitutions (positions 5 and 6) are well-tolerated. The hydrolytically unstable aromatic lactone is important for activity. Lactone hydrolysis rates were used as a measure of reactivity; hydrolysis rates correlate with inhibitory activity. The most potent Sir2 inhibitors were structurally similar to and had hydrolysis rates similar to 1.

  DOI：

  10.1021/jm030473r
• 作为产物：
  描述：

  丙烯酸 、 2,3-二羟基萘 在 Amberlyst 15 resin 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以55%的产率得到5-Hydroxy-1,2-dihydro-benzo[f]chromen-3-one
  参考文献：
  名称：

  Inhibitors of Sir2:  Evaluation of Splitomicin Analogues

  摘要：

  Splitomicin (1) and 41 analogues were prepared and evaluated in cell-based Sir2 inhibition and toxicity assays and an in vitro Sir2 inhibition assay. Lactone ring or naphthalene (positions 7-9) substituents decrease activity, but other naphthalene substitutions (positions 5 and 6) are well-tolerated. The hydrolytically unstable aromatic lactone is important for activity. Lactone hydrolysis rates were used as a measure of reactivity; hydrolysis rates correlate with inhibitory activity. The most potent Sir2 inhibitors were structurally similar to and had hydrolysis rates similar to 1.

  DOI：

  10.1021/jm030473r

文献信息

• Inhibitors of Sir2:  Evaluation of Splitomicin Analogues
  作者：Jeff Posakony、Maki Hirao、Sam Stevens、Julian A. Simon、Antonio Bedalov

  DOI：10.1021/jm030473r

  日期：2004.5.1

  Splitomicin (1) and 41 analogues were prepared and evaluated in cell-based Sir2 inhibition and toxicity assays and an in vitro Sir2 inhibition assay. Lactone ring or naphthalene (positions 7-9) substituents decrease activity, but other naphthalene substitutions (positions 5 and 6) are well-tolerated. The hydrolytically unstable aromatic lactone is important for activity. Lactone hydrolysis rates were used as a measure of reactivity; hydrolysis rates correlate with inhibitory activity. The most potent Sir2 inhibitors were structurally similar to and had hydrolysis rates similar to 1.