(1E,4E)-1-(3,5-dimethoxy-4-((1-(4-(tetrahydro-2H-pyran-2-yloxy)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one | 1217503-68-8

• 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-(3,5-dimethoxy-4-((1-(4-(tetrahydro-2H-pyran-2-yloxy)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one
• 英文别名: GO-Y061；(1E,4E)-1-[3,5-dimethoxy-4-[[1-[[4-(oxan-2-yloxy)phenyl]methyl]triazol-4-yl]methoxy]phenyl]-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one
• CAS: 1217503-68-8
• 化学式: C₃₇H₄₁N₃O₉
• 分子量: 671.747
• InChiKey: NWLLDQUAAKZMPD-UTLPMFLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-[4-(azidomethyl)phenoxy]oxane 、 (1E,4E)-1-(3,5-dimethoxy-4-(prop-2-ynyloxy)phenyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one 在 copper(l) iodide 作用下， 以 乙腈 为溶剂， 以81%的产率得到(1E,4E)-1-(3,5-dimethoxy-4-((1-(4-(tetrahydro-2H-pyran-2-yloxy)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-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