2-(hydroxymethyl)-3,4-dihydro-2H-chromen-4-ol | 583830-24-4

• 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: 2-(hydroxymethyl)-3,4-dihydro-2H-chromen-4-ol
• 英文别名: 2-(Hydroxymethyl)chroman-4-ol
• CAS: 583830-24-4
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: IEQIKWXHMYQYJL-UHFFFAOYSA-N

物化性质

• 沸点：
  342.7±35.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-3,4-dihydro-2H-chromen-4-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以77%的产率得到2-(羟甲基)-2,3-二氢色烯-4-酮
  参考文献：
  名称：

  In silico screening with benzofurane- and benzopyrane-type MDR-modulators

  摘要：

  Development of inhibitors of the drug efflux pump P-glycoprotein is a versatile approach to overcome multi drug resistance (MDR) in tumor therapy. In an approach to lower the conformational flexibility of the lead compound propafenone, we synthesized a set of dihydrobenzofuranes and benzopyranones. In the case of the 4 diastereomeric dihydrobenzofuranes, no significant differences in activity regarding the configuration on the side-chains at the dihydrofurane moiety (cis or trans) was observed. This may be due to the high flexibility of the side-chains, which still allow mutually overlap of pharmacophores. The benzopyranones showed a good correlation between lipophilicity and activity with gnerally lower logpotency/logP ratios. This decrease may be due to the rigidization of the molecules. In an in silico screening approach, a set of diverse propafenone-type compounds was used to establish a pharmacophore model, which was used to screen the world drug index. Among the hits retrieved there are several compounds, which were previously described as MDR-modulators. This demonstrates the validity of the model.

  DOI：

  10.1016/s0014-827x(03)00021-1
• 作为产物：
  描述：

  4-氧代-4H-苯并吡喃-2-羧酸甲酯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以84%的产率得到2-(hydroxymethyl)-3,4-dihydro-2H-chromen-4-ol
  参考文献：
  名称：

  In silico screening with benzofurane- and benzopyrane-type MDR-modulators

  摘要：

  Development of inhibitors of the drug efflux pump P-glycoprotein is a versatile approach to overcome multi drug resistance (MDR) in tumor therapy. In an approach to lower the conformational flexibility of the lead compound propafenone, we synthesized a set of dihydrobenzofuranes and benzopyranones. In the case of the 4 diastereomeric dihydrobenzofuranes, no significant differences in activity regarding the configuration on the side-chains at the dihydrofurane moiety (cis or trans) was observed. This may be due to the high flexibility of the side-chains, which still allow mutually overlap of pharmacophores. The benzopyranones showed a good correlation between lipophilicity and activity with gnerally lower logpotency/logP ratios. This decrease may be due to the rigidization of the molecules. In an in silico screening approach, a set of diverse propafenone-type compounds was used to establish a pharmacophore model, which was used to screen the world drug index. Among the hits retrieved there are several compounds, which were previously described as MDR-modulators. This demonstrates the validity of the model.

  DOI：

  10.1016/s0014-827x(03)00021-1

文献信息

• In silico screening with benzofurane- and benzopyrane-type MDR-modulators
  作者：Sascha Rebitzer、Danilo Annibali、Stephan Kopp、Monika Eder、Thierry Langer、Peter Chiba、Gerhard F Ecker、Christian R Noe

  DOI：10.1016/s0014-827x(03)00021-1

  日期：2003.3

  Development of inhibitors of the drug efflux pump P-glycoprotein is a versatile approach to overcome multi drug resistance (MDR) in tumor therapy. In an approach to lower the conformational flexibility of the lead compound propafenone, we synthesized a set of dihydrobenzofuranes and benzopyranones. In the case of the 4 diastereomeric dihydrobenzofuranes, no significant differences in activity regarding the configuration on the side-chains at the dihydrofurane moiety (cis or trans) was observed. This may be due to the high flexibility of the side-chains, which still allow mutually overlap of pharmacophores. The benzopyranones showed a good correlation between lipophilicity and activity with gnerally lower logpotency/logP ratios. This decrease may be due to the rigidization of the molecules. In an in silico screening approach, a set of diverse propafenone-type compounds was used to establish a pharmacophore model, which was used to screen the world drug index. Among the hits retrieved there are several compounds, which were previously described as MDR-modulators. This demonstrates the validity of the model.