(3E,5E)-3,5-bis(2-fluorobenzylidene)-1-methylpiperidin-4-one | 1434133-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3E,5E)-3,5-bis(2-fluorobenzylidene)-1-methylpiperidin-4-one
• 英文别名: (3E,5E)-3,5-bis[(2-fluorophenyl)methylidene]-1-methylpiperidin-4-one
• CAS: 1434133-36-4
• 化学式: C₂₀H₁₇F₂NO
• 分子量: 325.358
• InChiKey: IQMGGVXXZOIZMN-OTYYAQKOSA-N

物化性质

• 沸点：
  480.2±45.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E,5E)-3,5-bis(2-fluorobenzylidene)-1-methylpiperidin-4-one 、 噻莫西酸 、 苊醌 以 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到spiro[5.2'']acenaphthene-1''-onespiro[6.3']-5'-(2-fluorophenylmethylidene)-1'-methylpiperidin-4'-one-7-(2-fluorophenyl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole
  参考文献：
  名称：

  An atom economic synthesis and AChE inhibitory activity of novel dispiro 7-aryltetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole and 4-aryloctahydroindolizine N-methylpiperidin-4-one hybrid heterocycles

  摘要：

  The 1,3-dipolar cycloaddition of azomethine ylides generated in situ from acenaphthenequinone and alpha-amino acids viz. 1,3-thiazolone-4-carboxylic acid and piperidine-2-carboxylic acid to a series of 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones afforded novel spiro[5.2 '']acenaphthene-1 ''-onespiro[6.3']-5'-arylmethylidene-1'-methylpiperidin-4'-one-7-aryltetrahydro-1H-pyrrolo[12-c][1,3]thiazoles and spiro[2.2 '']acenaphthene-1 ''-onespiro[3.3']-5'-arylmethylidene-1'-methylpiperidin-4'-one-4-aryloctahydroindolizines respectively in quantitative yields. These compounds were evaluated for their AChE inhibitory activity and compound 3c was found to be the most potent with IC50 1.86 mu mol/L. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.050
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 2-氟苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以95.2%的产率得到(3E,5E)-3,5-bis(2-fluorobenzylidene)-1-methylpiperidin-4-one
  参考文献：
  名称：

  Discovery and evaluation of piperid-4-one-containing mono-carbonyl analogs of curcumin as anti-inflammatory agents

  摘要：

  We previously reported the design and discovery of three series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MCACs) as excellent anti-inflammatory agents. In continuation of our ongoing research, we designed and synthesized the fourth series of MCACs, whose central linker is a piperid-4-one. Their inhibitory effects against IL-6 production were evaluated in lipopolysaccharide (LPS)-stimulated macrophages. Among them, compounds F8, F29, F33, F35, and F36 exhibited the IC50 values under 5 mu M. The structure-activity relationship was discussed. Mechanistically, F35 and F36 dose-dependently prevented LPS-induced NF-kappa B and ERK activation. Finally, pretreatment with F35 and F36 significantly protected the C57B/L6 mice from LPS-induced septic death. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.057

文献信息

• Curcumin analogs with anti-tumor and anti-angiogenic properties
  申请人：——

  公开号：US20020019382A1

  公开（公告）日：2002-02-14

  The present invention is directed to curcumin analogs exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.

  本发明涉及表现出抗肿瘤和抗血管生成特性的姜黄素类似物，包括这些化合物的药物配方以及使用这些化合物的方法。
• [EN] CURCUMIN ANALOGUES FOR TREATING CANCER<br/>[FR] ANALOGUES DE CIRCUMINE DESTINES AU TRAITEMENT DU CANCER
  申请人：UNIV EMORY

  公开号：WO2001040188A1

  公开（公告）日：2001-06-07

  The present invention is directed to curcumin analogs (I), wherein Y is OH, halogen, or CF3; Z is H, OH, OR1, halogen, or CF3; X1 and X2 are independently C or N; and A is as defined in the application; exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.

  本发明涉及姜黄素类似物(I)，其中Y为OH、卤素或CF3；Z为H、OH、OR1、卤素或CF3；X1和X2独立地为C或N；A如本申请所定义；该类似物具有抗肿瘤和抗血管生成作用，制备包括这些化合物的制药组合物以及使用这些化合物的方法。
• CURCUMIN ANALOGS WITH ANTI-TUMOR AND ANTI-ANGIOGENIC PROPERTIES
  申请人：Snyder James P.

  公开号：US20080234320A1

  公开（公告）日：2008-09-25

  The present invention is directed to curcumin analogs exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.

  本发明涉及展现抗肿瘤和抗血管生成特性的姜黄素类似物，包括这些化合物的制药配方和使用这些化合物的方法。
• Novel dissymmetric 3,5-bis(arylidene)-4-piperidones as potential antitumor agents with biological evaluation in vitro and in vivo
  作者：Ning Li、Wen-Yu Xin、Bin-Rong Yao、Chun-Hua Wang、Wei Cong、Feng Zhao、Hong-Juan Li、Yun Hou、Qing-Guo Meng、Gui-Ge Hou

  DOI：10.1016/j.ejmech.2018.01.088

  日期：2018.3

  Thirty-five novel dissymmetric 3,5-bis(arylidene)-4-piperidone derivatives (BAPS, 6a-h, 7a-h, 8a-g, 9a-g, 10a-e) were synthesized and evaluated the cytotoxicity. BAPS 6d, 7h, 8g, 9g demonstrated the most potentially inhibitory activities against HepG2 and THP-1 but lower cytotoxicity toward LO2. In vitro, 6d, 7h, 8g, 9g can effectively up-regulate BAX expression, down-regulate Bcl-2 expression in HepG2 cell. They could reasonably bind to the active site of Bcl-2 protein proved by molecular docking modes. The most active BAP 6d induced HepG2 cells apoptosis in a dose-dependent manner by flow cytometrey. The cellular uptake of HepG2 cells showed 6d mainly accumulated into the nuclei by confocal laser scanning microscopy (CLSM). In vivo, 6d suppressed the growth of HepG2 xenografts in nude mice and relatively nontoxic to mice. These results suggest that 6d could be therapeutically beneficial as potential therapeutic agent for the early clinical treatment of liver cancers. (C) 2018 Elsevier Masson SAS. All rights reserved.
• CURCUMIN ANALOGUES FOR TREATING CANCER
  申请人：Emory University

  公开号：EP1242379A1

  公开（公告）日：2002-09-25