(1E,4E)-1-(2,4,5-trimethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one | 1217503-50-8

• 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: (1E,4E)-1-(2,4,5-trimethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one
• 英文别名: GO-Y093
• CAS: 1217503-50-8
• 化学式: C₂₃H₂₆O₇
• 分子量: 414.455
• InChiKey: FERHZDPEMHHPIA-FIFLTTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4,5-三甲氧基苯甲醛 、 (E)-4-(3,4,5-trimethoxyphenyl)but-3-en-2-one 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 (1E,4E)-1-(2,4,5-trimethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Structure–activity relationship of C5-curcuminoids and synthesis of their molecular probes thereof

  摘要：

  A series of novel analogues of 1,5-bis(4-hydroxy-3-methoxyphenyl)-penta-(1E,4E)-1,4-dien-3-one (C-5-curcumin), which is a natural analogue of curcumin isolated from the rhizomes of Curcuma domestica Val. (Zingiberacea), were synthesized and evaluated for their cytotoxicities against human colon cancer cell line HCT-116 to conclude the SAR of C-5-curcuminoids for further development of their use in cancer chemotherapy: (1) Bis(arylmethylidene) acetone serves as a promising skeleton for eliciting cytotoxicity. (2) The 3-oxo-1,4-pentadiene structure is essential for eliciting cytotoxicity. (3) As for the extent of the aromatic substituents, hexasubstituted compounds exhibit strong activities, in which 3,4,5-hexasubstitution results in the highest potency. (5) The symmetry between two aryl rings is not an essential requirement for bis(arylmethylidene) acetones to elicit cytotoxicity. (6) para-Positions allows the installation of additional functional groups for use as molecular probes. By taking advantage of the SAR diagram, we have elaborated several advanced derivatives having GI(50) of single-digit micromolar potencies that will function as molecular probes to target and/or report key biomolecules interacting with curcumin and C-5-curcumin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.045

文献信息

• Structure–activity relationship of C5-curcuminoids and synthesis of their molecular probes thereof
  作者：Hiroyuki Yamakoshi、Hisatsugu Ohori、Chieko Kudo、Atsuko Sato、Naoki Kanoh、Chikashi Ishioka、Hiroyuki Shibata、Yoshiharu Iwabuchi

  DOI：10.1016/j.bmc.2009.12.045

  日期：2010.2

  A series of novel analogues of 1,5-bis(4-hydroxy-3-methoxyphenyl)-penta-(1E,4E)-1,4-dien-3-one (C-5-curcumin), which is a natural analogue of curcumin isolated from the rhizomes of Curcuma domestica Val. (Zingiberacea), were synthesized and evaluated for their cytotoxicities against human colon cancer cell line HCT-116 to conclude the SAR of C-5-curcuminoids for further development of their use in cancer chemotherapy: (1) Bis(arylmethylidene) acetone serves as a promising skeleton for eliciting cytotoxicity. (2) The 3-oxo-1,4-pentadiene structure is essential for eliciting cytotoxicity. (3) As for the extent of the aromatic substituents, hexasubstituted compounds exhibit strong activities, in which 3,4,5-hexasubstitution results in the highest potency. (5) The symmetry between two aryl rings is not an essential requirement for bis(arylmethylidene) acetones to elicit cytotoxicity. (6) para-Positions allows the installation of additional functional groups for use as molecular probes. By taking advantage of the SAR diagram, we have elaborated several advanced derivatives having GI(50) of single-digit micromolar potencies that will function as molecular probes to target and/or report key biomolecules interacting with curcumin and C-5-curcumin. (C) 2010 Elsevier Ltd. All rights reserved.