1,5-bis(3-hydroxy-4-methoxyphenyl)penta-1,4-dien-3-one | 173534-21-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1,5-bis(3-hydroxy-4-methoxyphenyl)penta-1,4-dien-3-one
• CAS: 173534-21-9
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: XBMQVMWXMOLFRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-bis(3-hydroxy-4-methoxyphenyl)penta-1,4-dien-3-one 、 4-硝基苯肼 、 盐酸 在 乙醇 、 正己烷 作用下， 以 乙醇 为溶剂， 反应 52.0h， 以The product was obtained as orange-red microcrystals (37.2 g, 97.4 percent yield) mp 215°-217° C.的产率得到5-(3-Hydroxy-4-methoxyphenyl)-3-(3-hydroxy-4-methoxystyryl)-1-(4-nitrophenyl)-4,5-dihydropyrazole
  参考文献：
  名称：

  Nonlinear optically active pyrazolines and polymeric compositions

  摘要：

  本发明揭示了含有取代吡唑啉的化合物，其在定向时表现出非线性光学活性，并揭示了由此衍生的基团存在于聚合物的主链中的定向聚合物组成物。同时还揭示了制备本发明所述定向聚合物组成物的方法。

  公开号：

  US05466397A1
• 作为产物：
  描述：

  异香兰素 在 盐酸 、 4-甲基苯磺酸吡啶 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 1,5-bis(3-hydroxy-4-methoxyphenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.10.073

文献信息

• BIS(ARYLMETHYLIDENE)ACETONE COMPOUND, ANTI-CANCER AGENT, CARCINOGENESIS-PREVENTIVE AGENT, INHIBITOR OF EXPRESSION OF Ki-Ras, ErbB2, c-Myc AND CYCLINE D1, BETA-CATENIN-DEGRADING AGENT, AND p53 EXPRESSION ENHANCER
  申请人：Shibata Hiroyuki

  公开号：US20100152493A1

  公开（公告）日：2010-06-17

  It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.

  要改善姜黄素的溶解度，以开发一种能够在低浓度下抑制各种癌细胞生长的抗肿瘤化合物。因此，披露了一种新型合成化合物，双(芳基甲基亚乙酮)，具有优异的抗肿瘤活性和化学预防活性。合成并筛选了一种双(芳基甲基亚乙酮)（即具有姜黄素骨架的衍生物），它是一种抗肿瘤化合物并具有化学预防活性。可以合成具有增强抗肿瘤活性和化学预防活性的衍生物。
• Structure–activity relationship studies of curcumin analogues
  作者：James R. Fuchs、Bulbul Pandit、Deepak Bhasin、Jonathan P. Etter、Nicholas Regan、Dalia Abdelhamid、Chenglong Li、Jiayuh Lin、Pui-Kai Li

  DOI：10.1016/j.bmcl.2009.01.104

  日期：2009.4

  Two series of curcumin analogues, a total of twenty-four compounds, were synthesized and evaluated. The most potent compound, compound 23, showed potent growth inhibitory activities on both prostate and breast cancer lines with IC50 values in sub-micromolar range,fifty times more potent than curcumin. Curcumin analogues might be potential anti-tumor agents for breast and prostate cancers. (C) 2009 Elsevier Ltd. All rights reserved.
• US5466397A
  申请人：——

  公开号：US5466397A

  公开（公告）日：1995-11-14
• US8178727B2
  申请人：——

  公开号：US8178727B2

  公开（公告）日：2012-05-15
• 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.