6-Hydroxy-9-methyl-2,3-dihydro-1H-5,7-dioxa-dicyclopenta[a,g]naphthalen-4-one | 847798-00-9

• 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: 6-Hydroxy-9-methyl-2,3-dihydro-1H-5,7-dioxa-dicyclopenta[a,g]naphthalen-4-one
• CAS: 847798-00-9
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: LDDFUKUDTZDFCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.58
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-Hydroxy-9-methyl-2,3-dihydro-1H-5,7-dioxa-dicyclopenta[a,g]naphthalen-4-one 、 N,N-二甲氨基氯丙烷盐酸盐 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以64%的产率得到
  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 在 sodium hydroxide 、 三氯化铝 、 硫酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 66.0h， 生成 6-Hydroxy-9-methyl-2,3-dihydro-1H-5,7-dioxa-dicyclopenta[a,g]naphthalen-4-one
  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