((1E,4E)-3-oxopenta-1,4-diene-1,5-diyl)bis(2-methoxy-4,1-phenylene) dibenzoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: ((1E,4E)-3-oxopenta-1,4-diene-1,5-diyl)bis(2-methoxy-4,1-phenylene) dibenzoate
• 英文别名: 1,5-bis-(4-benzoyloxy-3-methoxy-phenyl)-penta-1,4-dien-3-one；1,5-Bis-(4-benzoyloxy-3-methoxy-phenyl)-penta-1,4-dien-3-on；3.3'-Dimethoxy-4.4'-dibenzoyloxy-dibenzylidenaceton；1,5-bis(4-benzoyloxy-3-methoxy-phenyl)penta-1,4-dien-3-one；[4-[(1E,4E)-5-(4-benzoyloxy-3-methoxyphenyl)-3-oxopenta-1,4-dienyl]-2-methoxyphenyl] benzoate
• 化学式: C₃₃H₂₆O₇
• 分子量: 534.565
• InChiKey: JKMBNNIPRVHQQL-HBKJEHTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (1E,4E)-1,5-bis[3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl]penta-1,4-dien-3-one 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ((1E,4E)-3-oxopenta-1,4-diene-1,5-diyl)bis(2-methoxy-4,1-phenylene) dibenzoate
  参考文献：
  名称：

  姜黄素单羰基类似物作为潜在抗肿瘤剂的合成及细胞毒性评价。

  摘要：

  临床前研究

  DOI：

  10.1002/ddr.21291

文献信息

• Discovery of Novel Mono-Carbonyl Curcumin Derivatives as Potential Anti-Hepatoma Agents
  作者：Weiya Cao、Pan Yu、Shilong Yang、Zheyu Li、Qixuan Zhang、Zengge Liu、Hongzhuo Li

  DOI：10.3390/molecules28196796

  日期：——

  Curcumin possesses a wide spectrum of liver cancer inhibition effects, yet it has chemical instability and poor metabolic properties as a drug candidate. To alleviate these problems, a series of new mono-carbonyl curcumin derivatives G1–G7 were designed, synthesized, and evaluated by in vitro and in vivo studies. Compound G2 was found to be the most potent derivative (IC50 = 15.39 μM) compared to curcumin (IC50 = 40.56 μM) by anti-proliferation assay. Subsequently, molecular docking, wound healing, transwell, JC-1 staining, and Western blotting experiments were performed, and it was found that compound G2 could suppress cell migration and induce cell apoptosis by inhibiting the phosphorylation of AKT and affecting the expression of apoptosis-related proteins. Moreover, the HepG2 cell xenograft model and H&E staining results confirmed that compound G2 was more effective than curcumin in inhibiting tumor growth. Hence, G2 is a promising leading compound with the potential to be developed as a chemotherapy agent for hepatocellular carcinoma.

  姜黄素具有广泛的肝癌抑制作用，但作为候选药物，它的化学性质不稳定，代谢特性较差。为了解决这些问题，研究人员设计、合成了一系列新的单羰基姜黄素衍生物 G1-G7，并通过体外和体内研究对其进行了评估。通过抗肿瘤实验发现，与姜黄素（IC50 = 40.56 μM）相比，化合物 G2 是最有效的衍生物（IC50 = 15.39 μM）。随后进行了分子对接、伤口愈合、Transwell、JC-1 染色和 Western 印迹实验，发现化合物 G2 可通过抑制 AKT 磷酸化和影响细胞凋亡相关蛋白的表达来抑制细胞迁移和诱导细胞凋亡。此外，HepG2 细胞异种移植模型和 H&E 染色结果证实，化合物 G2 在抑制肿瘤生长方面比姜黄素更有效。因此，G2 是一种很有潜力的先导化合物，有望开发为肝细胞癌的化疗药物。
• METHODS TO PREPARE PENTA-1,4-DIEN-3-ONES AND SUBSTITUTED CYCLOHEXANONES AND DERIVATIVES WITH ANTITUMORAL AND ANTIPARASITIC PROPERTIES, THE COMPOUNDS AND THEIR USES
  申请人：Uniban - Universidade Bandeirante De São Paulo

  公开号：EP2054365A2

  公开（公告）日：2009-05-06
• [EN] METHODS TO PREPARE PENTA-1,4-DIEN-3-ONES AND SUBSTITUTED CYCLOHEXANONES AND DERIVATIVES WITH ANTITUMORAL AND ANTIPARASITIC PROPERTIES, THE COMPOUNDS AND THEIR USES<br/>[FR] PROCÉDÉS DE PRÉPARATION DE PENTA-1,4-DIÈN-3-ONES ET DE CYCLOHEXANONES SUBSTITUÉS, DÉRIVÉS PRÉSENTANT DES PROPRIÉTÉS ANTITUMORALES ET ANTIPARASITIQUES, ET COMPOSÉS ET LEURS UTILISATIONS
  申请人：UNIBAN UNIVERSIDADE BANDEIRANT

  公开号：WO2008003155A2

  公开（公告）日：2008-01-10

  [EN] The present invention refers to new derivatives of the penta-1,4-dien-3-ones, as well as their processes of preparation. These compounds present strong antitumoral activity and promising antiparasitic action, behaving as almost atoxic by laboratory assays and also by hystopathologic studies. The present invention refers also to a pharmaceutical composition consisting of the referred compounds, method of treatment for cancer and parasitic diseases.
  [FR] La présente invention concerne de nouveaux dérivés de penta-1,4-dièn-3-ones, ainsi que leurs procédés de préparation. Ces composés présentent une forte activité antitumorale et une action antiparasitique prometteuse, se comportant presque de manière atoxique lors des essais en laboratoire, ainsi que lors d'études hystopathologiques. La présente invention concerne également une composition pharmaceutique comprenant lesdits composés, un procédé de traitement du cancer et des maladies parasitiques.
• Synthesis and Cytotoxic Evaluation of Monocarbonyl Analogs of Curcumin as Potential Anti‐Tumor Agents
  作者：Zheer Pan、Chengwei Chen、Yeli Zhou、Feng Xu、Yaozeng Xu

  DOI：10.1002/ddr.21291

  日期：2016.2

  Preclinical Research

  临床前研究