(2E)-1-(4-methylphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one | 56412-55-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-1-(4-methylphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one
• 英文别名: (E)-1-(4-methylphenyl)-3-naphthalen-1-ylprop-2-en-1-one
• CAS: 56412-55-6
• 化学式: C₂₀H₁₆O
• 分子量: 272.346
• InChiKey: FWCCLQQDGFXYFH-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E)-1-(4-methylphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one 在 哌啶 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.0h， 生成 ethyl 2-[3-cyano-6-(4-methylphenyl)-4-(1-naphthyl)pyrid-2-ylthio]acetate
  参考文献：
  名称：

  氰硫代乙酰胺的反应：几种新型硫代氢-吡啶-3-甲腈和噻吩并[2,3-b]吡啶衍生物的合成

  摘要：

  氰基硫代乙酰胺 (f 1) 与 α,β-不饱和羰基化合物 2a-d 反应得到 thioxohydropyridine-3-carbonitriles 5a-d，它被用作通过与活性含卤素化合物反应制备几种噻吩并吡啶的起始材料例如，2-溴-1-苯基乙酮(7a)、2-溴-1-对甲苯基-乙酮(7b)、氯丙酮(10a)、α-氯乙酰丙酮(10b)和氯乙酸乙酯(13)。新合成的杂环化合物的结构是基于元素分析、IR、 1 H NMR和质谱数据确定的。

  DOI：

  10.1080/10426500490475058
• 作为产物：
  描述：

  1-萘甲醛 、 对甲基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (2E)-1-(4-methylphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one
  参考文献：
  名称：

  3-芳基-4-芳基-1-（1H-咪唑-5-基）甲基吡咯，一类新的法呢基转移酶抑制剂。

  摘要：

  描述了作为法呢基转移酶抑制剂的一类3-芳基-4-芳基-1-（1H-咪唑-5-基）甲基吡咯的设计，合成及构效关系。化合物7抑制法呢基转移酶，IC（50）值为4.6 nM。

  DOI：

  10.1016/s0960-894x(01)00593-5

文献信息

• Design, modification and 3D QSAR studies of novel naphthalin-containing pyrazoline derivatives with/without thiourea skeleton as anticancer agents
  作者：Wen Yang、Yang Hu、Yu-Shun Yang、Fei Zhang、Yan-Bin Zhang、Xiao-Liang Wang、Jian-Feng Tang、Wei-Qing Zhong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2013.01.013

  日期：2013.3

  Two series of novel naphthalin-containing pyrazoline derivatives C1-C14 and D1-D14 have been synthesized and evaluated for their EGFR/HER-2 inhibitory and anti-proliferation activities. Compound D14 displayed the most potent activity against EGFR and A549 cell line (IC50 = 0.05 mu M and GI(50) = 0.11 mu M), being comparable with the positive control Erlotinib (IC50 = 0.03 mu M and GI(50) = 0.03 mu M) and more potent than our previous compounds C0-A (IC50 = 5.31 mu M and GI(50) = 33.47 mu M) and C0-B (IC50 = 0.09 mu M and GI(50) = 0.34 mu M). Meanwhile, compound C14 displayed the most potent activity against HER-2 and MCF-7 cell line (IC50 = 0.88 mu M and GI(50) = 0.35 mu M), being a little less potent than Erlotinib (IC50 = 0.16 mu M and GI(50) = 0.08 mu M) but far more potent than C0-A (IC50 = 6.58 mu M and GI(50) = 27.62 mu M) and C0-B (IC50 = 2.77 mu M and GI(50) = 3.79 mu M). The docking simulation was performed to analyze the probable binding models and the QSAR models were built for reasonable design of EGFR/HER-2 inhibitors at present and in future. The structural modification of introducing naphthalin moiety reinforced the combination of our compounds and the receptor, resulting in progress of bioactivity. Moreover, the replacement of thiourea skeleton by using benzene ring resulted in the slight diversity of the two series towards specific targets. (C) 2013 Elsevier Ltd. All rights reserved.
• LATIF N.; EL-BAYOUKI K., CHEM. AND IND. <CHIN-AG>, 1975, NO 7, 316
  作者：LATIF N.、 EL-BAYOUKI K.

  DOI：——

  日期：——
• [EN] METHOD FOR SCREENING FOR INHIBITORS OF ALZHEIMER'S DISEASE<br/>[FR] METHODE D'IDENTIFICATION D'INHIBITEURS DE LA MALADIE D'ALZHEIMER
  申请人：PRANA BIOTECHNOLOGY LTD

  公开号：WO2002048898A1

  公开（公告）日：2002-06-20

  This invention relates to compounds which have the ability to act as agonists for the binding of divalent copper ions to amyloid precursor protein (APP) and to methods of identifying such compounds by using the three-dimensional structure of the copper-binding domain of APP.