(1E,4Z,6E)-5-hydroxy-1,7-bis(3,4,5-trimethoxyphenyl)hepta-1,4,6-trien-3-one | 951132-46-0

• 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)-5-hydroxy-1,7-bis(3,4,5-trimethoxyphenyl)hepta-1,4,6-trien-3-one
• CAS: 951132-46-0
• 化学式: C₂₅H₂₈O₈
• 分子量: 456.493
• InChiKey: XVRXQXACEINYQL-HYSZJTPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1E,4Z,6E)-5-hydroxy-1,7-bis(3,4,5-trimethoxyphenyl)hepta-1,4,6-trien-3-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 以60%的产率得到(Z)-5-hydroxy-1,7-bis(3,4,5-trimethoxyphenyl)hept-4-en-3-one
  参考文献：
  名称：

  A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids

  摘要：

  Several curcuminoids and tetrahydrocurcuminoids (THCs), bearing various hydroxyl and/or methoxy groups on their benzene rings, have been synthesized to study their antioxidant and hydrogen donating capacities using the DPPH method at 25 degrees C in methanol. The results show that the tetrahydrocurcuminoids are in general much more efficient than their curcuminoid analogs if they include a phenol group in meta- or para-position of the linking chain and a neighboring phenol or methoxy group. This efficiency gain of THCs by comparison to curcuminoids was attributed to the presence of benzylic hydrogens involved in the oxidation process of these compounds and not to the beta-diketone moiety in the chain. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.085
• 作为产物：
  描述：

  乙酰丙酮 在 盐酸 、 boron trioxide 、 硼酸三丁酯 、 正丁胺 作用下， 生成 (1E,4Z,6E)-5-hydroxy-1,7-bis(3,4,5-trimethoxyphenyl)hepta-1,4,6-trien-3-one
  参考文献：
  名称：

  A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids

  摘要：

  Several curcuminoids and tetrahydrocurcuminoids (THCs), bearing various hydroxyl and/or methoxy groups on their benzene rings, have been synthesized to study their antioxidant and hydrogen donating capacities using the DPPH method at 25 degrees C in methanol. The results show that the tetrahydrocurcuminoids are in general much more efficient than their curcuminoid analogs if they include a phenol group in meta- or para-position of the linking chain and a neighboring phenol or methoxy group. This efficiency gain of THCs by comparison to curcuminoids was attributed to the presence of benzylic hydrogens involved in the oxidation process of these compounds and not to the beta-diketone moiety in the chain. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.085

文献信息

• Synthesis of Curcuminoids and Evaluation of Their Cytotoxic and Antioxidant Properties
  作者：María Lozada-García、Raúl Enríquez、Teresa Ramírez-Apán、Antonio Nieto-Camacho、Juan Palacios-Espinosa、Zeltzin Custodio-Galván、Olivia Soria-Arteche、Jaime Pérez-Villanueva

  DOI：10.3390/molecules22040633

  日期：——

  Curcumin (1) and ten derivatives (2-11) were synthesized and evaluated as cytotoxic and antioxidant agents. The results of primary screening by Sulforhodamine B assay against five human cancer cell lines (U-251 MG, glioblastoma; PC-3, human prostatic; HCT-15, human colorectal; K562, human chronic myelogenous leukemia; and SKLU-1, non-small cell lung cancer) allowed us to calculate the half maximal

  合成姜黄素（1）和十种衍生物（2-11）并作为细胞毒性和抗氧化剂进行评估。通过Sulforhodamine B分析对五种人类癌细胞系（U-251 MG，胶质母细胞瘤; PC-3，人类的前列腺癌; HCT-15，人类的结肠直肠癌; K562，人类的慢性粒细胞白血病; SKLU-1，非人类）进行初步筛选的结果-小细胞肺癌）使我们能够计算出对HCT-15和K562细胞系更具活性的化合物的半数最大抑制浓度（IC50）值。化合物2和10对两种细胞系均最具活性，并且比姜黄素本身更具活性。硫代巴比妥酸反应性物质（TBARS）分析表明，其中7种具有强活性。甚至比姜黄素，α-生育酚和槲皮素更强。
• Pharmacophore & QSAR Guided Design, Synthesis, Pharmacokinetics and In vitro Evaluation of Curcumin Analogs for Anticancer Activity
  作者：Sarfaraz Alam、Surjeet Verma、Kaneez Fatima、Suaib Luqman、Santosh Kumar Srivastava、Feroz Khan

  DOI：10.2174/0929867330666230428162720

  日期：2024.2

  synthesized curcumin analogs. Among the tested compounds, nine curcumin analogs were found with IC50 values of 0.10 to 1.86 µg/mL. The active analogs were assessed for pharmacokinetics compliance. EGFR was identified as a potential target of synthesized active curcumin analogs through docking studies. Conclusion: Integrating in silico design, QSAR-driven virtual screening, chemical synthesis, and experimental

  背景：作为我们发现基于植物的先导分子的一部分，我们提供了一个有用的工具，有助于姜黄素的识别、设计、优化、结构修饰和预测，以发现具有增强的生物利用度、药理学安全性和安全性的新型类似物。抗癌潜力。方法：开发了 QSAR（定量构效关系）和药效团作图模型，并进一步用于设计、合成、药代动力学和体外评估姜黄素类似物的抗癌活性。结果：QSAR 模型产生了 84% 的高活动-描述符关系精度 (r2)、81% 的高活动预测精度 (rcv2) 和 89% 的外部集预测精度。QSAR 研究表明，五种化学描述符与抗癌活性显着相关。确定的重要药效团特征是氢键受体、疏水中心和负电离中心。该模型的预测能力是针对一组化学合成的姜黄素类似物进行评估的。在测试的化合物中，发现了 9 种姜黄素类似物，IC50 值为 0.10 至 1.86 µg/mL。评估活性类似物的药代动力学依从性。通过对接研究，EGFR 被确定为合成活性姜
• Curcuminoid-inspired synthetic compounds as anti-tumor agents
  申请人：Laali Kenneth K.

  公开号：US10934241B2

  公开（公告）日：2021-03-02

  Novel CUR— and CUR—BF2 compounds exhibiting anti-tumor properties are presented. CUR compounds bearing fluorinated moieties with selective fluorine introduction into the α-carbonyl moiety as well as CUR—BF2 adducts and CURs with diverse substitution patterns in the phenyl rings including fluorinated substituents (SCF3, OCF3, and F) and/or bulky activating groups (OMe, OAc, and OBz) are presented. Fluorinated aryl-pyrazoles and isoxazoles as well as novel CUR and CUR—BF2 compounds with monocyclic aromatic and bicyclic-heteroaromatic lateral rings, bearing fluorine(s), OCF3, CF3, and SCF3 groups, and their alpha-carbonyl-fluorinated analogs, as well as their pyrazole and isoxazole derivatives are presented. The CUR-pyrazoles embody analogs that are fluorinated at the phenyl-pyrazole moiety. The compounds and their derivatives exhibited exceptional cytotoxic and anti-proliferative activity against several cancer cell-lines. Deuterated CUR—BF2 and CUR compounds were also synthesized.

  本文介绍了具有抗肿瘤特性的新型 CUR 和 CUR-BF2 化合物。介绍了在 α-羰基中选择性引入氟的含氟 CUR 化合物，以及 CUR- 加合物和在苯环中具有不同取代模式的 CUR，包括含氟取代基（S 、O 和 F）和/或大块活化基团（OMe、OAc 和 OBz）。介绍了含氟芳基吡唑和异噁唑，以及带有氟、O 、CF3 和 S 基团的单环芳香族和双环异芳香族侧环的新型 CUR 和 CUR- 化合物及其α-羰基氟化类似物，以及它们的吡唑和异噁唑衍生物。CUR 吡唑包含在苯基吡唑分子上氟化的类似物。这些化合物及其衍生物对几种癌细胞系具有卓越的细胞毒性和抗增殖活性。此外，还合成了氚代 CUR- 和 CUR 化合物。
• Synthesis and Identification of New 4-Arylidene Curcumin Analogues as Potential Anticancer Agents Targeting Nuclear Factor-κB Signaling Pathway
  作者：Xu Qiu、Yuhong Du、Bin Lou、Yinglin Zuo、Weiyan Shao、Yingpeng Huo、Jianing Huang、Yanjun Yu、Binhua Zhou、Jun Du、Haian Fu、Xianzhang Bu

  DOI：10.1021/jm1004545

  日期：2010.12.9

  A series of curcumin analogues including new 4-arylidene curcumin analogues (4-arylidene-1,7-bisarylhepta-1,6-diene-3,5-diones) were synthesized. Cell growth inhibition assays revealed that most 4-arylidene curcumin analogues can effectively decrease the growth of a panel of lung cancer cells at submicromolar and low micromolar concentrations. High content analysis technology coupled with biochemical studies showed that this new class of 4-arylidene curcumin analogues exhibits significantly improved NF-kappa B inhibition activity over the parent compound curcumin, at least in part by inhibiting I kappa B phosphorylation and degradation via IKK blockage; selected 4-arylidene curcumin analogues also reduced the tumorigenic potential of cancer cells in a clonogenic assay.
• Synthesis and evaluation of curcumin analogues as potential thioredoxin reductase inhibitors
  作者：Xu Qiu、Zhong Liu、Wei-Yan Shao、Xing Liu、Da-Ping Jing、Yan-Jun Yu、Lin-Kun An、Shi-Liang Huang、Xian-Zhang Bu、Zhi-Shu Huang、Lian-Quan Gu

  DOI：10.1016/j.bmc.2008.07.054

  日期：2008.9

  Series of curcumin derivatives were synthesized; the inhibitory activities on thioredoxin reductase (TrxR) of all analogues were evaluated by DTNB assay in vitro. It is found that most of the analogues can inhibit TrxR in the low micromolar range; Structure-activity relationship analysis reveals that analogues with furan moiety have excellent inhibitory effect on TrxR in an irreversible manner, indicating that the furan moiety may serve as a possible pharmacophore during the interaction of curcumin analogues with TrxR. The effect of selected curcuminoids on growth of different TrxR overexpressed cancer cell lines was also investigated and discussed. (C) 2008 Elsevier Ltd. All rights reserved.