(2E,6E)-2,6-bis(2-(trifluoromethyl)benzylidene)cyclohexanone | 1158188-81-8

• 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: (2E,6E)-2,6-bis(2-(trifluoromethyl)benzylidene)cyclohexanone
• 英文别名: (2E,6E)-2,6-Bis[2-(trifluoromethyl)benzylidene]cyclohexanone；(2E,6E)-2,6-bis[[2-(trifluoromethyl)phenyl]methylidene]cyclohexan-1-one
• CAS: 1158188-81-8
• 化学式: C₂₂H₁₆F₆O
• 分子量: 410.359
• InChiKey: UIVNNNYUCIGYPV-UNZYHPAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2E,6E)-2,6-bis(2-(trifluoromethyl)benzylidene)cyclohexanone 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以85%的产率得到(E,E)-2,6-bis(2-(trifluoromethyl)benzylidene)cyclohexanone oxime
  参考文献：
  名称：

  一种2,6-二苯亚甲基环己酮肟类化合物及其制备方法和应用

  摘要：

  本发明属于抗炎药物技术领域，公开了一种2,6‑二苯亚甲基环己酮肟类化合物及其制备方法和应用。本发明在2,6‑二苯亚甲基环己酮肟类化合物中引入了具有抗炎活性的结构片段，制得的化合物理化性质稳定。实验表明2,6‑二苯亚甲基环己酮肟类化合物具有优秀的炎症因子的抑制作用以及更好的体内抗炎活性，尤其是对于由TNF‑α和/或IL‑6超出正常量表达和释放而导致的肝炎和脂肪肝，而且对肝脏炎症以及脏脂质代谢具有保护作用。

  公开号：

  CN114853630B
• 作为产物：
  描述：

  邻三氟甲基苯甲醛 、 环己酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以81%的产率得到(2E,6E)-2,6-bis(2-(trifluoromethyl)benzylidene)cyclohexanone
  参考文献：
  名称：

  Synthesis of bis(ylidene) cyclohexanones and their antifungal activity against selected plant pathogenic fungi

  摘要：

  灰霉病菌（Botrytis cinerea）、根霉病菌（Rhizoctonia solani）和半知菌（Hemileia vastatrix）是导致全球作物遭受重大损失的三种植物病原真菌。这些真菌被选为目标模型，用于测试一系列双（亚甲基）环己酮的杀菌潜力。虽然已知该化学类别的一些化合物对人类病原体具有抑制活性，但直到现在，人们还从未探索过它们对植物病原体的控制作用。本研究通过简单、快速和低成本的碱或酸催化醛醇缩合反应合成了双(亚甲基吡啶)环己酮，并对 B. cinerea、R. solani 和 H. vastatrix 进行了体外测试。当以 200  nmol/菌丝栓测试 R. solani.时，这些化合物完全抑制了菌丝的生长，活性最强的双（吡啶亚甲基）环己酮化合物的 IC50 为 155.5 nmol 栓-1。此外，双（吡啶基亚甲基）环己酮化合物在 125 μmol L-1 的浓度下完全抑制了 H. vastatrix 的楔形孢子萌发。活性最强的双（吡啶基亚甲基）环己酮的 IC50 值为 4.8 μmol L-1，估计比用作对照的氧氯化铜杀菌剂低约 2.6 倍。此外，这些物质对哺乳动物 Vero 细胞系的细胞毒性较低。最后，硅学计算表明，这些化合物具有适合用作农用化学品的物理化学参数。双(亚乙基)环己酮可能是开发新型抗真菌剂的理想候选物质，可用于控制农业中的相关真菌疾病。

  DOI：

  10.1007/s11030-022-10431-7

文献信息

• Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents
  作者：Guang Liang、Lili Shao、Yi Wang、Chengguang Zhao、Yanhui Chu、Jian Xiao、Yu Zhao、Xiaokun Li、Shulin Yang

  DOI：10.1016/j.bmc.2008.10.044

  日期：2009.3

  Curcumin has a surprisingly wide range of chemo-preventive and chemo-therapeutic activities and is under investigation for the treatment of various human cancers. However, the clinical application of curcumin has been significantly limited by its instability and poor metabolic property. Although a number of synthetic modi. cations of curcumin have been studied intensively in order to develop a molecule with enhanced bioactivities, few synthetic studies were done for the improvement of pharmacokinetic profiles. In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which was considered to be responsible for the pharmacokinetic limitation of curcumin. The results of the in vitro stability studies and in vivo pharmacokinetic studies indicated that the stability of these mono-carbonyl analogues was greatly enhanced in vitro and their pharmacokinetic profiles were also significantly improved in vivo. Furthermore, the cytotoxic activities of mono-carbonyl analogues were evaluated in seven different tumor cell lines by MTT assay and the structure-activity relation (SAR) was discussed and concluded. The results suggest that the five-carbon linker-containing analogues of curcumin may be favorable for the curcumin-based drug development both pharmacokinetically and pharmacologically. (C) 2009 Published by Elsevier Ltd.
• [EN] MEDICINE FOR TREATING KIDNEY AND HEART DISEASE AND THE USES THEREOF<br/>[FR] MÉDICAMENT POUR LE TRAITEMENT DE MALADIES RÉNALES ET CARDIAQUES ET SES UTILISATIONS
  申请人：WENZHOU MEDICAL COLLEGE

  公开号：WO2012163088A3

  公开（公告）日：2013-01-24

  [EN] The present invention provides (2E, 6E)-2, 6 bis (2-(trifluoromethyl) benzylidene) cyclohexanone or the pharmaceutically acceptable salts thereof for use in the preparation of medicines to treat or prevent kidney or heart disease, or for use in medicines to ameliorate the symptoms of kidney or heart disease.
  [FR] La présente invention concerne la (2E,6E)-2,6-bis(2-(trifluorométhyl) benzylidène)cyclohexanone ou ses sels pharmaceutiquement acceptables destinés à être utilisés dans la préparation de médicaments pour traiter ou prévenir des maladies rénales ou cardiaques, ou à être utilisés dans des médicaments pour améliorer les symptômes de maladies rénales ou cardiaques.
• Synthesis of bis(ylidene) cyclohexanones and their antifungal activity against selected plant pathogenic fungi
  作者：Ueveton Pimentel da Silva、Bruno Wesley Ferreira、Bianca Lana de Sousa、Robert Weingart Barreto、Felipe Terra Martins、João Honorato de A. Neto、Boniek Gontijo Vaz、Rodolfo Rodrigues da Silva、Thaís Viana Fialho Martins、Tiago Antônio de Oliveira Mendes、Eduardo Vinícius Vieira Varejão

  DOI：10.1007/s11030-022-10431-7

  日期：2023.2

  Botrytis cinerea, Rhizoctonia solani and Hemileia vastatrix are three species of phytopathogenic fungi behind major crop losses worldwide. These have been selected as target models for testing the fungicide potential of a series of bis(ylidene) cyclohexanones. Although some compounds of this chemical class are known to have inhibitory activity against human pathogens, they have never been explored for the control of phytopathogens until now. In the present work, bis(ylidene) cyclohexanones were synthesized through simple, fast and low-cost base- or acid-catalyzed aldol condensation reaction and tested in vitro against B. cinerea, R. solani and H. vastatrix. bis(pyridylmethylene) cyclohexanones showed the highest activity against the target fungi. When tested at 200 nmol per mycelial plug against R. solani., these compounds completely inhibited the mycelial growth, and the most active bis(pyridylmethylene) cyclohexanone compound had an IC50 of 155.5 nmol plug−1. Additionally, bis(pyridylmethylene) cyclohexanones completely inhibited urediniospore germination of H. vastatrix, at 125 μmol L−1. The most active bis(pyridylmethylene) cyclohexanone had an IC50 value of 4.8 µmol L−1, which was estimated as approximately 2.6 times lower than that found for the copper oxychloride-based fungicide, used as control. Additionally, these substances had a low cytotoxicity against the mammalian Vero cell line. Finally, in silico calculations indicated that these compounds present physicochemical parameters regarded as suitable for agrochemicals. Bis(ylidene) cyclohexanones may constitute promising candidates for the development of novel antifungal agents for the control of relevant fungal diseases in agriculture.

  灰霉病菌（Botrytis cinerea）、根霉病菌（Rhizoctonia solani）和半知菌（Hemileia vastatrix）是导致全球作物遭受重大损失的三种植物病原真菌。这些真菌被选为目标模型，用于测试一系列双（亚甲基）环己酮的杀菌潜力。虽然已知该化学类别的一些化合物对人类病原体具有抑制活性，但直到现在，人们还从未探索过它们对植物病原体的控制作用。本研究通过简单、快速和低成本的碱或酸催化醛醇缩合反应合成了双(亚甲基吡啶)环己酮，并对 B. cinerea、R. solani 和 H. vastatrix 进行了体外测试。当以 200  nmol/菌丝栓测试 R. solani.时，这些化合物完全抑制了菌丝的生长，活性最强的双（吡啶亚甲基）环己酮化合物的 IC50 为 155.5 nmol 栓-1。此外，双（吡啶基亚甲基）环己酮化合物在 125 μmol L-1 的浓度下完全抑制了 H. vastatrix 的楔形孢子萌发。活性最强的双（吡啶基亚甲基）环己酮的 IC50 值为 4.8 μmol L-1，估计比用作对照的氧氯化铜杀菌剂低约 2.6 倍。此外，这些物质对哺乳动物 Vero 细胞系的细胞毒性较低。最后，硅学计算表明，这些化合物具有适合用作农用化学品的物理化学参数。双(亚乙基)环己酮可能是开发新型抗真菌剂的理想候选物质，可用于控制农业中的相关真菌疾病。
• 一种2,6-二苯亚甲基环己酮肟类化合物及其制备方法和应用
  申请人：温州医科大学

  公开号：CN114853630B

  公开（公告）日：2023-06-27

  本发明属于抗炎药物技术领域，公开了一种2,6‑二苯亚甲基环己酮肟类化合物及其制备方法和应用。本发明在2,6‑二苯亚甲基环己酮肟类化合物中引入了具有抗炎活性的结构片段，制得的化合物理化性质稳定。实验表明2,6‑二苯亚甲基环己酮肟类化合物具有优秀的炎症因子的抑制作用以及更好的体内抗炎活性，尤其是对于由TNF‑α和/或IL‑6超出正常量表达和释放而导致的肝炎和脂肪肝，而且对肝脏炎症以及脏脂质代谢具有保护作用。