7-hydroxy-8-methoxy-3,4-trimethylenecoumarin | 847797-97-1

• 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: 7-hydroxy-8-methoxy-3,4-trimethylenecoumarin
• 英文别名: 7-hydroxy-6-methoxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one；7-hydroxy-6-methoxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one
• CAS: 847797-97-1
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: IJAWHLPCANTTRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-hydroxy-8-methoxy-3,4-trimethylenecoumarin 在 sodium hydroxide 、 三氯化铝 、 sodium hydride 、 potassium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 63.0h， 生成
  参考文献：
  名称：

  Design, synthesis and photobiological properties of 3,4-cyclopentenepsoralens

  摘要：

  The QSAR directed synthesis of tetracyclic psoralen derivatives (3-5) characterised by the condensation of a cyclopentane ring at the level of the 3,4 double bond of the tricyclic psoralen moiety is reported. The new compounds present a methoxy (3). a hydroxy (4) or a dimethylaminopropoxy (5) side chain inserted in position 8 of the lead chromophore. The evaluation of photoantiproliferative activity on human tumour cell lines reveals for 5 an ability to inhibit cell growth significantly higher with respect to that of the reference drug, 8-MOP. Interestingly, the enhancement in antiproliferative activity is accompanied by the disappearance of skin phototoxicity. On the other hand, no significant photobiological activity was scored for 3 and 4. The ability to photoreact with DNA. evaluated by isolating the 4',5' monoadduct and by estimating the ability to form interstrand cross-links, appeared to be significant for 5. practically negligible for 3 and 4. Furthermore, a back-projection of the more active compound identifies structural features suitable for further synthetic modifications. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.044
• 作为产物：
  描述：

  2-甲氧基间苯二酚 、 2-氧代环戊羧酸乙酯 在 硫酸 作用下， 反应 15.0h， 以91%的产率得到7-hydroxy-8-methoxy-3,4-trimethylenecoumarin
  参考文献：
  名称：

  Design, synthesis and photobiological properties of 3,4-cyclopentenepsoralens

  摘要：

  The QSAR directed synthesis of tetracyclic psoralen derivatives (3-5) characterised by the condensation of a cyclopentane ring at the level of the 3,4 double bond of the tricyclic psoralen moiety is reported. The new compounds present a methoxy (3). a hydroxy (4) or a dimethylaminopropoxy (5) side chain inserted in position 8 of the lead chromophore. The evaluation of photoantiproliferative activity on human tumour cell lines reveals for 5 an ability to inhibit cell growth significantly higher with respect to that of the reference drug, 8-MOP. Interestingly, the enhancement in antiproliferative activity is accompanied by the disappearance of skin phototoxicity. On the other hand, no significant photobiological activity was scored for 3 and 4. The ability to photoreact with DNA. evaluated by isolating the 4',5' monoadduct and by estimating the ability to form interstrand cross-links, appeared to be significant for 5. practically negligible for 3 and 4. Furthermore, a back-projection of the more active compound identifies structural features suitable for further synthetic modifications. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.044

文献信息

• Design, synthesis and photobiological properties of 3,4-cyclopentenepsoralens
  作者：Ornella Gia、Sebastiano Marciani Magno、Humberto Gonzalez-Diaz、Elias Quezada、Lourdes Santana、Eugenio Uriarte、Lisa Dalla Via

  DOI：10.1016/j.bmc.2004.10.044

  日期：2005.2

  The QSAR directed synthesis of tetracyclic psoralen derivatives (3-5) characterised by the condensation of a cyclopentane ring at the level of the 3,4 double bond of the tricyclic psoralen moiety is reported. The new compounds present a methoxy (3). a hydroxy (4) or a dimethylaminopropoxy (5) side chain inserted in position 8 of the lead chromophore. The evaluation of photoantiproliferative activity on human tumour cell lines reveals for 5 an ability to inhibit cell growth significantly higher with respect to that of the reference drug, 8-MOP. Interestingly, the enhancement in antiproliferative activity is accompanied by the disappearance of skin phototoxicity. On the other hand, no significant photobiological activity was scored for 3 and 4. The ability to photoreact with DNA. evaluated by isolating the 4',5' monoadduct and by estimating the ability to form interstrand cross-links, appeared to be significant for 5. practically negligible for 3 and 4. Furthermore, a back-projection of the more active compound identifies structural features suitable for further synthetic modifications. (C) 2004 Elsevier Ltd. All rights reserved.