(2E,6E)-2-(3,5-dimethoxybenzylidene)-6-(2-fluorobenzylidene)cyclohexanone | 1417561-45-5

• 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-(3,5-dimethoxybenzylidene)-6-(2-fluorobenzylidene)cyclohexanone
• 英文别名: (2E,6E)-2-[(3,5-dimethoxyphenyl)methylidene]-6-[(2-fluorophenyl)methylidene]cyclohexan-1-one
• CAS: 1417561-45-5
• 化学式: C₂₂H₂₁FO₃
• 分子量: 352.405
• InChiKey: CLEKNGMKRNGHMK-YAUBYZHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-2-(3,5-dimethoxybenzylidene)cyclohexanone 、 2-氟苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以85%的产率得到(2E,6E)-2-(3,5-dimethoxybenzylidene)-6-(2-fluorobenzylidene)cyclohexanone
  参考文献：
  名称：

  Design, synthesis and molecular docking of α,β-unsaturated cyclohexanone analogous of curcumin as potent EGFR inhibitors with antiproliferative activity

  摘要：

  A type of novel alpha,beta-unsaturated cyclohexanone analogous, which designed based on the curcumin core structure, have been discovered as potential EGFR inhibitors. These compounds exhibit potent antiproliferative activity in two human tumor cell lines (Hep G2 and B16-F10). Among them, compounds I-3 and I-12 displayed the most potent EGFR inhibitory activity (IC50 = 0.43 mu M and 1.54 mu M, respectively). Molecular docking of I-12 into EGFR TK active site was also performed. This inhibitor nicely fitting the active site might well explain its excellent inhibitory activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.031

文献信息

• alpha-(3,5-dimethoxybenzylidene)-alpha'-hydrocarbyl methylene cyclic ketone and preparation method thereof
  申请人：PHARMAXYN LABORATORIES LTD.

  公开号：US20150259271A1

  公开（公告）日：2015-09-17

  The present invention discloses a α-(3,5-dimethoxybenzylidene)-α′-hydrocarbyl methylene cyclic ketone with the following formula: wherein R is aryl or alkyl, its preparation method is: the cyclic ketone blended with morpholine are subjected to azeotropic dehydration to give enamine, the enamine is condensed with 3,5-dimethoxybenzaldehyde and then condensed with alkyl or aryl formaldehyde under acidic or basic conditions to give the product, the present invention further discloses an antitumor agent comprising α-(3,5-dimethoxybenzylidene)-α′-hydrocarbyl methylene cyclic ketone or medically acceptable salts and pharmaceutically acceptable carriers thereof. Through the above, the present invention provides α-(3,5-dimethoxybenzylidene)-α′-hydrocarbyl methylene cyclic ketone and preparation method thereof, the said compound is a high activity antitumor agent obtained by piecing and modifying the formulas of natural anti-tumor active ingredient resveratrol and curcumin, which has a good inhibitory effect on epidermal growth factor receptor.

  本发明揭示了一种具有以下结构式的 α-(3,5-二甲氧基苄亚基)-α′-烃基亚甲基环酮：其中 R 为芳基或烷基，其制备方法为：将环酮与吗啉混合物经过共沸脱水得到烯胺，将烯胺与3,5-二甲氧基苄醛缩合，然后在酸性或碱性条件下与烷基或芳基甲醛缩合得到产物，本发明还揭示了包含 α-(3,5-二甲氧基苄亚基)-α′-烃基亚甲基环酮或其医学上可接受的盐和药学上可接受的载体的抗肿瘤剂。通过上述方法，本发明提供了α-(3,5-二甲氧基苄亚基)-α′-烃基亚甲基环酮及其制备方法，该化合物是通过拼接和修改天然抗肿瘤活性成分白藜芦醇和姜黄素的结构式而获得的高活性抗肿瘤剂，对表皮生长因子受体具有良好的抑制作用。
• A-(3,5-DIMETHOXY BENZYLIDENE)-A'-HYDROCARBYL METHYLENE CYCLIC KETONE AND PREPARATION METHOD THEREOF
  申请人：Pharmaxyn Laboratories Ltd.

  公开号：EP2927208A1

  公开（公告）日：2015-10-07

  The present invention discloses a α-(3,5-dimethoxybenzylidene)-α'-hydrocarbyl methylene cyclic ketone with the following structure: or wherein R is aryl or alkyl, its preparation method is: the cyclic ketone blended with morpholine are subjected to azeotropic dehydration to give enamine, the enamine is condensed with 3,5-dimethoxybenzaldehyde and then condensed with alkyl or aryl formaldehyde under acidic or basic conditions to give the product, the present invention further discloses an antitumor agent comprising α-(3,5-dimethoxybenzylidene)-α'-hydrocarbyl methylene cyclic ketone or medically acceptable salts and pharmaceutically acceptable carriers thereof. Through the above, the present invention providesα-(3,5-dimethoxybenzylidene)-α'-hydrocarbyl methylene cyclic ketone and preparation method thereof, the said compound is a high activity antitumor agent obtained by piecing and modifying the structures of natural anti-tumor active ingredient resveratrol and curcumin, which has a good inhibitory effect on epidermal growth factor receptor.

  本发明公开了一种结构如下的α-(3,5-二甲氧基亚苄基)-α'-氢羰基亚甲基环酮： 或 其中 R 为芳基或烷基，其制备方法为环酮与吗啉共沸脱水得到烯胺，烯胺与3,5-二甲氧基苯甲醛缩合，然后在酸性或碱性条件下与烷基或芳基甲醛缩合得到产品、本发明进一步公开了一种抗肿瘤剂，包括α-(3,5-二甲氧基亚苄基)-α'-氢羰基亚甲基环酮或医学上可接受的盐及其药学上可接受的载体。综上所述，本发明提供了α-(3,5-二甲氧基亚苄基)-α'-氢羰基亚甲基环酮及其制备方法，该化合物是通过对天然抗肿瘤活性成分白藜芦醇和姜黄素的结构进行拼接和修饰而得到的一种高活性抗肿瘤剂，对表皮生长因子受体具有良好的抑制作用。
• US9409845B2
  申请人：——

  公开号：US9409845B2

  公开（公告）日：2016-08-09
• Design, synthesis and molecular docking of α,β-unsaturated cyclohexanone analogous of curcumin as potent EGFR inhibitors with antiproliferative activity
  作者：Yun-Yun Xu、Yi Cao、Hailkuo Ma、Huan-Qiu Li、Gui-Zhen Ao

  DOI：10.1016/j.bmc.2012.11.031

  日期：2013.1

  A type of novel alpha,beta-unsaturated cyclohexanone analogous, which designed based on the curcumin core structure, have been discovered as potential EGFR inhibitors. These compounds exhibit potent antiproliferative activity in two human tumor cell lines (Hep G2 and B16-F10). Among them, compounds I-3 and I-12 displayed the most potent EGFR inhibitory activity (IC50 = 0.43 mu M and 1.54 mu M, respectively). Molecular docking of I-12 into EGFR TK active site was also performed. This inhibitor nicely fitting the active site might well explain its excellent inhibitory activity. (C) 2012 Elsevier Ltd. All rights reserved.