(2E,5E)-2,5-bis(3-(allyloxy)-4-methoxybenzylidene)cyclopentanone | 1158188-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2E,5E)-2,5-bis(3-(allyloxy)-4-methoxybenzylidene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis[(4-methoxy-3-prop-2-enoxyphenyl)methylidene]cyclopentan-1-one
• CAS: 1158188-68-1
• 化学式: C₂₇H₂₈O₅
• 分子量: 432.516
• InChiKey: QNRWWQHNGZINJY-YHARCJFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-烯丙氧基-4-甲氧基苯甲醛 、 环戊酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以53.8%的产率得到(2E,5E)-2,5-bis(3-(allyloxy)-4-methoxybenzylidene)cyclopentanone
  参考文献：
  名称：

  Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents

  摘要：

  Curcumin has a surprisingly wide range of chemo-preventive and chemo-therapeutic activities and is under investigation for the treatment of various human cancers. However, the clinical application of curcumin has been significantly limited by its instability and poor metabolic property. Although a number of synthetic modi. cations of curcumin have been studied intensively in order to develop a molecule with enhanced bioactivities, few synthetic studies were done for the improvement of pharmacokinetic profiles. In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which was considered to be responsible for the pharmacokinetic limitation of curcumin. The results of the in vitro stability studies and in vivo pharmacokinetic studies indicated that the stability of these mono-carbonyl analogues was greatly enhanced in vitro and their pharmacokinetic profiles were also significantly improved in vivo. Furthermore, the cytotoxic activities of mono-carbonyl analogues were evaluated in seven different tumor cell lines by MTT assay and the structure-activity relation (SAR) was discussed and concluded. The results suggest that the five-carbon linker-containing analogues of curcumin may be favorable for the curcumin-based drug development both pharmacokinetically and pharmacologically. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.10.044