4-methyl-7-(2'-oxocyclopentyloxy)coumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-methyl-7-(2'-oxocyclopentyloxy)coumarin
• 英文别名: 4-methyl-7-(2-oxocyclopentyloxy)-2H-chromen-2-one；4-methyl-7-(2-oxocyclopentyl)oxychromen-2-one
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: UDCMJKJFGCMHHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-7-(2'-oxocyclopentyloxy)coumarin 在 sodium hydroxide 、 水 作用下， 反应 24.0h， 以43%的产率得到4-methylcyclopentenefuro<3,2-g>coumarin
  参考文献：
  名称：

  Photobiological studies of new cyclopentene–psoralens

  摘要：

  Psoralen analogues bearing a cyclopentane ring fused to either the 4',5' double bond (compound 4) or the 3,4 double bond (compound 7) of the tricyclic furocoumarin structure were prepared. AM1 theoretical calculations performed for these compounds indicated that the electronic properties of their reactive double bonds were very similar to those of psoralen and its derivative 8-methoxypsoralen (8-MOP), though the overall molecular geometries were clearly different, particularly as regards the change in molecular curvature produced by the introduction of the cyclopentane ring. Compound 4 showed a capacity similar to that of 8-MOP to inhibit the growth of human cervix adenocarcinoma cells (HeLa) and to induce mutagenic effects, but it was definitely less phototoxic to skin than 8-MOP. Its ability to photoadd to DNA and to cross-link DNA strands was also demonstrated. Instead. compound 7 was practically devoid of biological activity and no interaction with the macromolecule could be detected. These differences in behaviour between 4 and 7 are probably due to the molecular curvature resulting fi om the introduction of the cyclopentane ring. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00079-2
• 作为产物：
  描述：

  2-氯环戊酮 、 羟甲香豆素 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 4-methyl-7-(2'-oxocyclopentyloxy)coumarin
  参考文献：
  名称：

  A QSAR Model for in Silico Screening of MAO-A Inhibitors. Prediction, Synthesis, and Biological Assay of Novel Coumarins

  摘要：

  This work explores the potential of the MARCH-INSIDE methodology to seek a QSAR for MAO-A inhibitors from a heterogeneous series of compounds. A Markov model was used to quickly calculate the molecular electron delocalization, polarizability, refractivity, and n-octanol/water partition coefficients for a series of 1406 active/nonactive compounds. LDA was subsequently used to fit a classification function. The model showed 92.8% and 91.8% global accuracy and predictability in training and validation studies. This QSAR model was validated through a virtual screening of a series of cournarin derivatives. The 15 selected compounds were prepared and evaluated as in vitro MAO-A inhibitors. The theoretical prediction was' compared with the experimental results and the model correctly predicted 13 compounds with only two mistakes on compounds with activities very close to the cutoff point established for the model. Consequently, this method represents a useful tool for the "in silico" screening of MAO-A inhibitors.

  DOI：

  10.1021/jm0509849

文献信息

• Photobiological studies of new cyclopentene–psoralens
  作者：Lisa Dalla Via、Ornella Gia、Giampietro Viola、Giulio Bertoloni、Lourdes Santana、Eugenio Uriarte

  DOI：10.1016/s0014-827x(98)00079-2

  日期：1998.11

  Psoralen analogues bearing a cyclopentane ring fused to either the 4',5' double bond (compound 4) or the 3,4 double bond (compound 7) of the tricyclic furocoumarin structure were prepared. AM1 theoretical calculations performed for these compounds indicated that the electronic properties of their reactive double bonds were very similar to those of psoralen and its derivative 8-methoxypsoralen (8-MOP), though the overall molecular geometries were clearly different, particularly as regards the change in molecular curvature produced by the introduction of the cyclopentane ring. Compound 4 showed a capacity similar to that of 8-MOP to inhibit the growth of human cervix adenocarcinoma cells (HeLa) and to induce mutagenic effects, but it was definitely less phototoxic to skin than 8-MOP. Its ability to photoadd to DNA and to cross-link DNA strands was also demonstrated. Instead. compound 7 was practically devoid of biological activity and no interaction with the macromolecule could be detected. These differences in behaviour between 4 and 7 are probably due to the molecular curvature resulting fi om the introduction of the cyclopentane ring. (C) 1998 Elsevier Science S.A. All rights reserved.
• A QSAR Model for in Silico Screening of MAO-A Inhibitors. Prediction, Synthesis, and Biological Assay of Novel Coumarins
  作者：Lourdes Santana、Eugenio Uriarte、Humberto González-Díaz、Giuseppe Zagotto、Ramón Soto-Otero、Estefanía Méndez-Álvarez

  DOI：10.1021/jm0509849

  日期：2006.2.1

  This work explores the potential of the MARCH-INSIDE methodology to seek a QSAR for MAO-A inhibitors from a heterogeneous series of compounds. A Markov model was used to quickly calculate the molecular electron delocalization, polarizability, refractivity, and n-octanol/water partition coefficients for a series of 1406 active/nonactive compounds. LDA was subsequently used to fit a classification function. The model showed 92.8% and 91.8% global accuracy and predictability in training and validation studies. This QSAR model was validated through a virtual screening of a series of cournarin derivatives. The 15 selected compounds were prepared and evaluated as in vitro MAO-A inhibitors. The theoretical prediction was' compared with the experimental results and the model correctly predicted 13 compounds with only two mistakes on compounds with activities very close to the cutoff point established for the model. Consequently, this method represents a useful tool for the "in silico" screening of MAO-A inhibitors.