10-(4-((2,6-dimethoxy-4-((1E,4E)-3-oxo-5-(3,4,5-trimethoxyphenyl)penta-1,4-dienyl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)decyl 2-((3,5,6-trimethyl-1,7-dioxo-1,7-dihydropyrazolo[1,2-a]pyrazol-2-yl)methylthio)ethanoate | 1217503-69-9

• 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: 10-(4-((2,6-dimethoxy-4-((1E,4E)-3-oxo-5-(3,4,5-trimethoxyphenyl)penta-1,4-dienyl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)decyl 2-((3,5,6-trimethyl-1,7-dioxo-1,7-dihydropyrazolo[1,2-a]pyrazol-2-yl)methylthio)ethanoate
• 英文别名: GO-Y080；10-[4-[[2,6-dimethoxy-4-[(1E,4E)-3-oxo-5-(3,4,5-trimethoxyphenyl)penta-1,4-dienyl]phenoxy]methyl]triazol-1-yl]decyl 2-[(1,2,7-trimethyl-3,5-dioxopyrazolo[1,2-a]pyrazol-6-yl)methylsulfanyl]acetate
• CAS: 1217503-69-9
• 化学式: C₄₇H₅₉N₅O₁₁S
• 分子量: 902.078
• InChiKey: KGNXXUNYCCOQHB-XPWSMXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  64
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  195
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  、 (1E,4E)-1-(4-((1-(10-hydroxydecyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,5-di-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one 在 4-吡咯烷基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 以30%的产率得到10-(4-((2,6-dimethoxy-4-((1E,4E)-3-oxo-5-(3,4,5-trimethoxyphenyl)penta-1,4-dienyl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)decyl 2-((3,5,6-trimethyl-1,7-dioxo-1,7-dihydropyrazolo[1,2-a]pyrazol-2-yl)methylthio)ethanoate
  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