(1E,4E)-1,5-bis(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one | 17537-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1E,4E)-1,5-bis(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one
• CAS: 17537-28-9
• 化学式: C₂₃H₂₆O₇
• 分子量: 414.455
• InChiKey: QMBQAUFXKZCNOT-FIFLTTCUSA-N

物化性质

• 熔点：
  113-115 °C(Solv: ethanol (64-17-5))
• 沸点：
  579.0±50.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1,5-bis(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以51%的产率得到1,5-bis(3,4,5-trimethoxyphenyl)pentan-3-one
  参考文献：
  名称：

  Synthesis and Antimalarial Activity of Dihydroperoxides and Tetraoxanes Conjugated with Bis(benzyl)acetone Derivatives

  摘要：

  Dihydroperoxides and tetraoxanes derived from symmetrically substituted bis(arylmethyl)acetones were synthesized in modest to good yields using several methods. Three of these compounds exhibit an important in vitro antimalarial activity (1.0 μm ≤ IC50 ≤ 5.0 μm) against blood forms of the human malaria parasite Plasmodium falciparum.

  DOI：

  10.1111/j.1747-0285.2012.01345.x
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 丙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (1E,4E)-1,5-bis(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis of New 2-(5-Aryl-3-styryl-4,5-dihydro-1H-pyrazol-1-yl)-4-(trifluoromethyl)pyrimidines

  摘要：

  一系列2-（5-芳基-3-苯乙烯基-4,5-二氢-1H-吡唑-1-基）-4-（三氟甲基）嘧啶通过5-芳基-1-羧酰亚胺基-3-苯乙烯基-4,5-二氢-1H-吡唑与4-烷氧基-1,1,1-三氟-3-烯-2-酮的环化缩合反应合成。在Ti(Oi-Pr)4或BF3·OEt2的催化下，高效的环化反应以良好产率得到目标嘧啶。确定了乙基3-[2-(5-苯基-3-苯乙烯基-4,5-二氢-1H-吡唑-1-基)-4-(三氟甲基)嘧啶-6-基]丙酸酯的晶体结构。

  DOI：

  10.1055/s-2006-942431

文献信息

• Synthesis and Anti-bacterial Properties of Mono-carbonyl Analogues of Curcumin
  作者：Guang Liang、Shulin Yang、Lijuan Jiang、Yu Zhao、Lili Shao、Jian Xiao、Faqing Ye、Yueru Li、Xiaokun Li

  DOI：10.1248/cpb.56.162

  日期：——

  The synthesis of three series of curcumin analogues with mono-carbonyl is described. Their in vitro anti-bacterial activities against seven Gram-positive and Gram-negative bacteria were tested and the effect of substituents on the aryl ring and the space structure of the linking strain were discussed. It was observed that part of the derivatives displayed significant activity when compared with curcumin and most of them exhibited activity against the ampicillin-resisted Enterobacter cloacae. Compounds A12, B09, B13, B14 and C09 show remarkable antibacterial activity in vitro. The result showed that heterocycle or long-chain substituents may enhance the activity of curcumin analogues.

  本文描述了三种单羰基姜黄素类似物的合成。对七种革兰氏阳性和革兰氏阴性细菌进行了体外抗菌活性测试，并讨论了取代基对芳环和连接张力的空间结构的影响。观察到，与姜黄素相比，部分衍生物显示出显著的活性，并且大多数衍生物对氨苄西林抵抗的阴沟肠杆菌表现出活性。化合物A12、B09、B13、B14和C09显示出显著的体外抗菌活性。结果显示，杂环或长链取代基可能增强姜黄素类似物的活性。
• 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。
• Photophysical and charge transport properties of pyrazolines
  作者：Joseph Ajantha、Elumalai Varathan、Vishal Bharti、Venkatesan Subramanian、Shanmugam Easwaramoorthi、Suresh Chand

  DOI：10.1039/c5ra19520a

  日期：——

  Pyrazoline, an intense green emitting molecule both in solution and solid state, with extended π-conjugation has been synthesized via simple two-step reactions in high yields.

  吡唑啉，一种在溶液和固态下均具有强烈绿色发射的分子，具有扩展的π-共轭，已经通过简单两步反应以高收率合成。

• Synthesis, characterization and antichagasic evaluation of thiosemicarbazones prepared from chalcones and dibenzalacetones
  作者：Aline Alves da Silva、Pedro Ivo da Silva Maia、Carla Duque Lopes、Sergio de Albuquerque、Marcelo Siqueira Valle

  DOI：10.1016/j.molstruc.2021.130014

  日期：2021.5

  causes of death from infectious diseases. In view of the severity of this pathology, this work describes the synthesis of new thiosemicarbazones derived from chalcones and dibenzalacetones as potential drugs for the treatment of this disease. The structures of all compounds were elucidated by infrared (IR) and nuclear magnetic resonance (1H and 13C NMR) spectroscopies. The chalcone derived thiosemicarbazones

  恰加斯病是一种被忽视的疾病，是传染病致死的主要原因之一。考虑到这种病理学的严重性，这项工作描述了衍生自查耳酮和二苯扎丙酮的新型硫代半咔唑的合成方法，这些药物可作为治疗这种疾病的潜在药物。通过红外光谱和核磁共振波谱（1 H和13 C NMR）阐明了所有化合物的结构。查耳酮缩氨基硫脲衍生的10 - 14被针对的原生动物细胞内无鞭毛体形式测试克氏锥虫，不得不使用LLC-MK2细胞其细胞毒性进行评估。化合物10（IC 50 与标准药物苯硝唑（IC 50  = 5.64 µM）相比，MHC = 12.25 µM）具有最佳活性。
• Synthesis of (±)-7-(3,4,5-trimethoxyphenyl)-7-deoxyidarubicinone. A new family of anthracycline analogues
  作者：Esther Caballero、Manuel Medarde、Rafael Pelaez-Lamamie de Clairac、Heidi Sahagún、Fernando Tomé

  DOI：10.1016/s0040-4020(98)00304-4

  日期：1998.5

  The synthesis of the first representative compound of 7-aryl anthracycline analogues, is described. 1-Alkyl-3-trialkylsiloxydienes, prepared from readily available materials, are transformed through a Diels-Alder cycloaddition into a tetracyclic ketone, that is converted into (±)-7-(3,4,5-trimethoxyphenyl)-7-deoxyidarubicinone. The conformations of the target compound and intermediate products are

  描述了7-芳基蒽环类似物的第一代表性化合物的合成。用Diels-Alder环加成法将由容易获得的材料制得的1-烷基-3-三烷基甲硅烷氧基二烯转化为四环酮，然后将其转化为（±）-7-（3,4,5-三甲氧基苯基）-7-脱氧柔红霉素。研究了目标化合物和中间产物的构象。