1,5-双(3-羟基-4-甲氧基苯基)戊-1,4-二烯-3-酮 | 917813-56-0

• 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
• 中文名称: 1,5-双(3-羟基-4-甲氧基苯基)戊-1,4-二烯-3-酮
• 英文名称: (1E,4E)-1,5-bis(3-hydroxy-4-methoxyphenyl)penta-1,4-dien-3-one
• CAS: 917813-56-0
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: XBMQVMWXMOLFRT-FCXRPNKRSA-N

物化性质

• 熔点：
  195-197 °C(Solv: methanol (67-56-1))
• 沸点：
  591.0±50.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  异香兰素 、 丙酮 在 1-hexyl-3-methylimidazolium salicylate 作用下， 以 水 为溶剂， 反应 0.42h， 以93.92%的产率得到1,5-双(3-羟基-4-甲氧基苯基)戊-1,4-二烯-3-酮
  参考文献：
  名称：

  超分子聚合聚集行为及其对咪唑基亲水性离子液体催化性能的影响

  摘要：

  离子液体（ILs）自组装形成超分子聚合物簇/聚集体。IL的聚集行为影响其在有机合成中的活性。但是，IL在有机反应中的确切作用仍是未知的。因此，重要的是要理解IL的超分子聚合聚集行为。我们正在使用电喷雾电离质谱（ESI-MS）探索IL的超分子聚合聚集行为。我们已经合成了四个亲水性IL（1-4），并研究了它们的聚集行为及其对碳-碳键形成（Knoevenagel和Claisen-Schmidt缩合）催化活性的影响。在这里，我们表明IL的聚集行为取决于阳离子和阴离子的类型和性质。ESI-MS（-ve）光谱揭示了两种不同类型的聚集，即[C n A n + 1 ] -和[A 2  + H + ] -。我们发现，催化活性随[C n A n + 1 ] -超分子聚集的增加而增加。因此，在IL中获得的最高收率的产品显示出阴离子-阴离子聚集的减少[A 2  + H +] – ESI-MS中的丰度。我们预计我们

  DOI：

  10.1016/j.molliq.2019.112372

文献信息

• BIS(ARYLMETHYLIDENE)ACETONE COMPOUND, ANTI-CANCER AGENT, CARCINOGENESIS-PREVENTIVE AGENT, INHIBITOR OF EXPRESSION OF Ki-Ras, ErbB2, c-Myc AND CYCLINE D1, BETA-CATENIN-DEGRADING AGENT, AND p53 EXPRESSION ENHANCER
  申请人：Shibata Hiroyuki

  公开号：US20100152493A1

  公开（公告）日：2010-06-17

  It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.

  要改善姜黄素的溶解度，以开发一种能够在低浓度下抑制各种癌细胞生长的抗肿瘤化合物。因此，披露了一种新型合成化合物，双(芳基甲基亚乙酮)，具有优异的抗肿瘤活性和化学预防活性。合成并筛选了一种双(芳基甲基亚乙酮)（即具有姜黄素骨架的衍生物），它是一种抗肿瘤化合物并具有化学预防活性。可以合成具有增强抗肿瘤活性和化学预防活性的衍生物。
• Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant Candida spp.
  作者：Fei Zhao、Huai-Huai Dong、Yuan-Hua Wang、Tian-Yi Wang、Ze-Hao Yan、Fang Yan、Da-Zhi Zhang、Ying-Ying Cao、Yong-Sheng Jin

  DOI：10.1039/c6md00649c

  日期：——

  monoketone derivatives of curcumin were synthesized to investigate the synergy with fluconazole against fluconazole-resistant Candida spp. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant C. albicans, C. tropicalis and C. krusei in vitro. Most of these compounds showed

  合成了二十三种姜黄素单酮衍生物，以研究与氟康唑对耐氟康唑的念珠菌的协同作用。在体外测定了抗真菌增效剂氟康唑的最低抑菌浓度（MIC 80）和分数抑菌浓度指数（FICI）对耐氟康唑的白色念珠菌，热带念珠菌和克鲁氏梭菌的抑制作用。这些化合物中的大多数对热带念珠菌表现出良好的协同活性。其中，化合物9显示出对念珠菌的显着协同活性。spp。特区也进行了讨论。特别地，细胞生长测试显示，1μgml -1氟康唑和64μgml -1或128μgml -1化合物9的组合显示出对热带假丝酵母最有效的杀真菌作用。协同作用可能与细胞内ATP含量和细胞膜通透性的变化有关。我们的结果为这些化合物作为氟康唑耐药念珠菌病的治疗方法的潜在线​​索提供了未来评估和开发的基础。
• Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin
  作者：Lorraine M. Deck、Lucy A. Hunsaker、Thomas A. Vander Jagt、Lisa J. Whalen、Robert E. Royer、David L. Vander Jagt

  DOI：10.1016/j.ejmech.2017.11.048

  日期：2018.1

  Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability, to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues. (C) 2017 Published by Elsevier Masson SAS.
• Synthesis and assessment of the antioxidant and antitumor properties of asymmetric curcumin analogues
  作者：Qingyong Li、Jian Chen、Shuyue Luo、Jialin Xu、Qiaoxian Huang、Tianyu Liu

  DOI：10.1016/j.ejmech.2015.02.005

  日期：2015.3

  In this study, 12 asymmetric curcumin (CUR) analogues and 5 symmetric curcumin derivatives were synthesized, the antioxidant activity of these derivatives were evaluated by radicals 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay, 2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) assay, ROO center dot (TRAP) assay and O2-center dot (NET) assay and anti-proliferative activities of these analogues were assessed against the human hepatoma cell line (SMMC-7721), the human breast cancer cell line (MCF-7) and the human prostate cancer cell lines (PC-3). Most of the asymmetric compounds showed stronger antioxidant activities than Vitamin C (Vc). Curcumin analogues reducing free radicals contain two reaction mechanisms: H-atom and electron transfer mechanisms. Compound 14 showed the most significant antioxidant activity compared with curcumin and other derivatives. Shorted the carbon chain of 14 can reduce the O-H bond dissociation enthalpy (BED) to improve the antioxidant activity. The antioxidant activity of 25 was similar to curcumin. All of the compounds performed better in an anti-proliferate assay than curcumin, especially compound 25, which exhibited the preferential cytotoxic activity against MCF-7 cells(25, IC50 = 9.11 mu M, curcumin, IC50 = 70.2 mu M). Considering these data, future studies should be performed to assess the therapeutic values of these asymmetric curcumin analogues. (C) 2015 Elsevier Masson SAS. All rights reserved.
• US5466397A
  申请人：——

  公开号：US5466397A

  公开（公告）日：1995-11-14