(1E,4Z,6E)-1,7-bis(4-(benzyloxy)-3-methoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (1E,4Z,6E)-1,7-bis(4-(benzyloxy)-3-methoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one
• 英文别名: (1E,4Z,6E)-5-hydroxy-1,7-bis(3-methoxy-4-phenylmethoxyphenyl)hepta-1,4,6-trien-3-one
• 化学式: C₃₅H₃₂O₆
• 分子量: 548.635
• InChiKey: RBSKFDAYDNFIJS-FICPWARLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三氟化硼乙醚 、 (1E,4Z,6E)-1,7-bis(4-(benzyloxy)-3-methoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one 在 potassium carbonate 作用下， 以 乙醚 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  非细胞毒性二苄基和二氟硼酸盐类姜黄素荧光团允许在生物成像中观察细胞核或细胞质

  摘要：

  姜黄素是从 Curcuma longa 中分离出的最重要的次级代谢物，以其众多声称的治疗特性和作为天然染料而闻名。在此，基于姜黄素的固有荧光，进行了对改进的基于姜黄素的荧光团的搜索。在半合成姜黄素衍生物组中，即单 (1)、二 (2)、三 (3)、四 (4) 苄基化和二苄基-氟硼酸盐 (5)，溶液中 2 和 5 的荧光特性优于与姜黄素相比，量子产率提高了两倍。此外，所有苄基化衍生物在以 25 μM 筛选抗人类癌症和非肿瘤 COS-7 细胞系时都显示出有利的最小细胞毒活性，其细胞毒作用与取代程度有关。荧光团 2 和 5 是多功能生物成像工具，如共聚焦荧光显微镜 (CFM) 所揭示，并显示星形胶质细胞和星形细胞瘤的活细胞膜的渗透。当 2 用 405-（蓝色）或 543-nm（绿色）激光激发时，可以专门和密集地可视化细胞核。然而，随着激光波长移向红色区域，荧光发射会减弱。相比之下，当使用 560 nm

  DOI：

  10.3390/molecules25143205
• 作为产物：
  描述：

  curcumin 、 溴甲苯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以38%的产率得到(1E,4Z,6E)-1,7-bis(4-(benzyloxy)-3-methoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Influence of side-chain changes on histone deacetylase inhibitory and cytotoxicity activities of curcuminoid derivatives

  摘要：

  Using curcuminoids as lead compounds, fifty-nine curcuminoid derivatives with different side chains at the phenolic moiety were synthesized. All compounds were investigated for their histone deacetylase (HDAC) inhibitory activities. The potent pan-HDAC inhibitors were further tested against three human cancer cell lines including Hela, HCT116 and MCF-7 with MTT-based assay. The bisethylamide 4z and the mono-sec-butyl derivative 5j manifested good antiproliferative activities against HCT116 cancer cells with the IC50 values as 14.60 +/- 1.19 mu g/mL and 7.33 +/- 0.98 mu g/mL, respectively. Molecular docking study of both compounds with Class I HDACs revealed that the compounds might bind tightly to the binding pocket of HDAC2. These findings suggested that these compounds can be putative candidates for the development of anticancer drugs via inhibiting HDACs.

  DOI：

  10.1016/j.bmcl.2020.127171

文献信息

• Influence of side-chain changes on histone deacetylase inhibitory and cytotoxicity activities of curcuminoid derivatives
  作者：La-or Somsakeesit、Thanaset Senawong、Pakit Kumboonma、Somprasong Saenglee、Arunta Samankul、Gulsiri Senawong、Chavi Yenjai、Chanokbhorn Phaosiri

  DOI：10.1016/j.bmcl.2020.127171

  日期：2020.6

  Using curcuminoids as lead compounds, fifty-nine curcuminoid derivatives with different side chains at the phenolic moiety were synthesized. All compounds were investigated for their histone deacetylase (HDAC) inhibitory activities. The potent pan-HDAC inhibitors were further tested against three human cancer cell lines including Hela, HCT116 and MCF-7 with MTT-based assay. The bisethylamide 4z and the mono-sec-butyl derivative 5j manifested good antiproliferative activities against HCT116 cancer cells with the IC50 values as 14.60 +/- 1.19 mu g/mL and 7.33 +/- 0.98 mu g/mL, respectively. Molecular docking study of both compounds with Class I HDACs revealed that the compounds might bind tightly to the binding pocket of HDAC2. These findings suggested that these compounds can be putative candidates for the development of anticancer drugs via inhibiting HDACs.
• Non-Cytotoxic Dibenzyl and Difluoroborate Curcuminoid Fluorophores Allow Visualization of Nucleus or Cytoplasm in Bioimaging
  作者：Marco A. Obregón-Mendoza、Imilla I. Arias-Olguín、M. Mirian Estévez-Carmona、William Meza-Morales、Yair Alvarez-Ricardo、Rubén A. Toscano、Francisco Arenas-Huertero、Julia Cassani、Raúl G. Enríquez

  DOI：10.3390/molecules25143205

  日期：——

  Curcumin, the most important secondary metabolite isolated from Curcuma longa, is known for its numerous purported therapeutic properties and as a natural dye. Herein, based on curcumin’s intrinsic fluorescence, a search for improved curcumin-based fluorophores was conducted. Within the set of semi-synthetic curcumin derivatives i.e. mono (1), di (2), tri (3), tetra (4) benzylated and dibenzyl-fluoroborate

  姜黄素是从 Curcuma longa 中分离出的最重要的次级代谢物，以其众多声称的治疗特性和作为天然染料而闻名。在此，基于姜黄素的固有荧光，进行了对改进的基于姜黄素的荧光团的搜索。在半合成姜黄素衍生物组中，即单 (1)、二 (2)、三 (3)、四 (4) 苄基化和二苄基-氟硼酸盐 (5)，溶液中 2 和 5 的荧光特性优于与姜黄素相比，量子产率提高了两倍。此外，所有苄基化衍生物在以 25 μM 筛选抗人类癌症和非肿瘤 COS-7 细胞系时都显示出有利的最小细胞毒活性，其细胞毒作用与取代程度有关。荧光团 2 和 5 是多功能生物成像工具，如共聚焦荧光显微镜 (CFM) 所揭示，并显示星形胶质细胞和星形细胞瘤的活细胞膜的渗透。当 2 用 405-（蓝色）或 543-nm（绿色）激光激发时，可以专门和密集地可视化细胞核。然而，随着激光波长移向红色区域，荧光发射会减弱。相比之下，当使用 560 nm