9-methyl-2,3-dihydrocyclopenta[c]furo[3,2-g]chromen-4(1H)-one

• 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: 9-methyl-2,3-dihydrocyclopenta[c]furo[3,2-g]chromen-4(1H)-one
• 英文别名: 3,4-cyclopenten-4'-methylfuro<3,2-g>coumarin；14-methyl-8,12-dioxatetracyclo[7.7.0.02,6.011,15]hexadeca-1(9),2(6),10,13,15-pentaen-7-one
• 化学式: C₁₅H₁₂O₃
• mdl: MFCD01881538
• 分子量: 240.258
• InChiKey: FGMQQMRIDDBLDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-(2-oxopropoxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 在 sodium hydroxide 、 水 作用下， 反应 20.0h， 以66%的产率得到9-methyl-2,3-dihydrocyclopenta[c]furo[3,2-g]chromen-4(1H)-one
  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

文献信息

• ——
  作者：M. M. Garazd、Ya. L. Garazd、S. V. Shilin、T. N. Panteleimonova、V. P. Khilya

  DOI：10.1023/a:1020423826071

  日期：——

  Psoralen and allopsoralen analogs that contain an annelated cyclopentane were synthesized from 7-hydroxy- and 9-hydroxy-1,2,3,4-tetrahydrocyclopenta[c]chromen-4-ones. 9-Phenyl-1,2,3,4-tetrahydrocyclopenta[c]furo[3,2-g]chromen-4-one exhibited low toxicity, acted as a CNS stimulant, and exhibited cardiotropic activity.
• METHODS AND SYSTEMS FOR TREATING CELL PROLIFERATION DISORDERS WITH PSORALEN DERIVATIVES
  申请人：Immunolight, LLC

  公开号：US20180169433A1

  公开（公告）日：2018-06-21

  Psoralen compounds of compounds having formulae 1A-10A, 1B-10B, 1C-10C, 1D-10D, 1E-10E, 1F-10F, 1G-10G, and 1H-5H as shown in FIG. 1, and pharmaceutically acceptable salts thereof; and their use in methods for the treatment of a cell proliferation disorder in a subject, pharmaceutical compositions containing the psoralen derivatives, a kit for performing the method, and a method for causing an autovaccine effect in a subject using the method.
• 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.