2,5-bis-(3,4-difluorobenzylidene)cyclopentanone | 137096-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis-(3,4-difluorobenzylidene)cyclopentanone
• 英文别名: 2,5-bis(3,4-difluorobenzylidene)cyclopentanone；2,5-Bis[(3,4-difluorophenyl)methylidene]cyclopentan-1-one；2,5-bis[(3,4-difluorophenyl)methylidene]cyclopentan-1-one
• CAS: 137096-60-7
• 化学式: C₁₉H₁₂F₄O
• mdl: MFCD14722923
• 分子量: 332.297
• InChiKey: LQAJSJHJZPIQBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二氟苯甲醛 、 环戊酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2,5-bis-(3,4-difluorobenzylidene)cyclopentanone
  参考文献：
  名称：

  Hopkin, Sian E.; Muir, Maxwell; Theocharis, Charis R., Journal of the Chemical Society. Perkin transactions II, 1991, p. 1131 - 1135

  摘要：

  DOI：

文献信息

• Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway
  作者：Pay-Chin Leow、Priti Bahety、Choon Pei Boon、Chong Yew Lee、Kheng Lin Tan、Tianming Yang、Pui-Lai Rachel Ee

  DOI：10.1016/j.ejmech.2013.10.073

  日期：2014.1

  Osteosarcoma is a primary bone malignancy with aggressive metastatic potential and poor prognosis rates. In our earlier work we have investigated the therapeutic potential of curcumin as an anti-invasive agent in osteosarcoma by its ability to regulate the Wnt/beta-catenin signaling pathway. However, the clinical use of curcumin is limited owing to its low potency and poor pharmacokinetic profile. In this study, an attempt was made to achieve more potent Wnt inhibitory activity in osteosarcoma cells by carrying out synthetic chemical modifications of curcumin. We synthesized a total of five series consisting of 43 curcumin analogs and screened in HEK293T cells for inhibition of beta-catenin transcriptional activity. Six promising analogs, which were 6.5- to 60-fold more potent than curcumin in inhibiting Wnt activity, were further assessed for their anti-invasive activity and Wnt inhibitory mechanisms. Western blot analysis showed disruption of beta-catenin protein nuclear translocation following treatment with analogs 2f, 3c and 4f. Using transwell assays, we also found that these compounds were more potent than la (curcumin) in impeding the invasion of osteosarcoma cells, possibly through suppressing MMP-9 activity. Structure-activity-relationship studies revealed that Wnt inhibitory effects could be enhanced by shortening and restraining the flexibility of the 7-carbon linker moiety connecting the terminal aromatic rings of curcumin and substituting both rings with appropriate substituents. Our results demonstrate that the synthesized curcumin analogs are more potent Wnt inhibitors in osteosarcoma cell lines as compared to parental curcumin and are good lead compounds for further development. Future in vivo tests with these compounds will define their therapeutic potentials as promising drug candidates for clinical treatment of osteosarcoma. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Hopkin, Sian E.; Muir, Maxwell; Theocharis, Charis R., Journal of the Chemical Society. Perkin transactions II, 1991, p. 1131 - 1135
  作者：Hopkin, Sian E.、Muir, Maxwell、Theocharis, Charis R.

  DOI：——

  日期：——