1,5-bis(3,5-dimethoxy-4-hydroxyphenyl)-1,4-pentadien-3-one | 66567-15-5

• 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(3,5-dimethoxy-4-hydroxyphenyl)-1,4-pentadien-3-one
• 英文别名: 1,5-bis(4-hydroxy-3,5-dimethoxyphenyl)penta-1,4-dien-3-one
• CAS: 66567-15-5
• 化学式: C₂₁H₂₂O₇
• 分子量: 386.401
• InChiKey: DDGVRFAFSCAHHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,5-bis(3,5-dimethoxy-4-hydroxyphenyl)-1,4-pentadien-3-one 、 氨基磺酰氯 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 [4-[5-(3,5-dimethoxy-4-sulfamoyloxyphenyl)-3-oxopenta-1,4-dienyl]-2,6-dimethoxyphenyl] sulfamate
  参考文献：
  名称：

  Structure–activity relationship studies of curcumin analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.01.104
• 作为产物：
  描述：

  丙酮 、 丁香醛 在 盐酸 、 水 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 生成 1,5-bis(3,5-dimethoxy-4-hydroxyphenyl)-1,4-pentadien-3-one
  参考文献：
  名称：

  Structure–activity relationship studies of curcumin analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.01.104

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。
• US8178727B2
  申请人：——

  公开号：US8178727B2

  公开（公告）日：2012-05-15
• 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.