(E)-1-(4-bromophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one | 36715-55-6

• 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: (E)-1-(4-bromophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one
• 英文别名: 1-(4-bromophenyl)-3-(2-naphthyl)-2-propen-1-one；(2E)-1-(4'-bromophenyl)-3-(2-naphthyl)-2-propen-1-one；1-(4-bromo-phenyl)-3t-[2]naphthyl-propenone；1-(4-Brom-phenyl)-3t-[2]naphthyl-propenon；1-(4-Bromophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one；(E)-1-(4-bromophenyl)-3-naphthalen-2-ylprop-2-en-1-one
• CAS: 36715-55-6
• 化学式: C₁₉H₁₃BrO
• 分子量: 337.216
• InChiKey: IYGLNQJEXFHQQP-WUXMJOGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (E)-1-(4-bromophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one 在 1,4-二氧六环 、 铂 作用下， 生成 1-(4-bromo-phenyl)-3-[2]naphthyl-propan-1-one
  参考文献：
  名称：

  THE REARRANGEMENT OF ARYL-SUBSTITUTED PROPYNES TO ALLENES¹

  摘要：

  DOI：

  10.1021/jo01137a023
• 作为产物：
  描述：

  4-溴苯乙酮 、 2-萘甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 25.0h， 以99%的产率得到(E)-1-(4-bromophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  查尔酮衍生物作为卵巢癌细胞生长抑制剂的合成及其构效关系

  摘要：

  背景：卵巢癌仍然是一种五年生存率很低的疾病。因此，需要新颖的疗法。天然查耳酮及其合成衍生物已在包括抑制癌细胞生长在内的许多领域显示出生物活性。 目的：建立查尔酮衍生物文库，包括新颖的结构，并确定其对卵巢癌细胞生长的抑制作用及其与结构-活性的关系。 方法：用取代的苯乙酮与芳族醛之间的Claisen-Schmidt缩合反应，以中等至极好的收率和良好的纯度生产了一系列新型查耳酮。用MTS测定法测量CA-OV3细胞的细胞增殖。 结果：在34种合成化合物中，有8种是新衍生物。合成的化合物通过1 H NMR，13 C NMR和HRMS进行表征。在CA-OV3细胞中对这些β-苯基丙烯酮衍生物进行的生物学评估显示出有趣的抗增殖活性，提供了初始结构-活性信息。 结论：在34种测试的化合物中，有14种显示出显着的活性，其中一些显示在100 µM时几乎完全抑制了生长。结构-活性关系表明，对A环的修饰是宽容的，对

  DOI：

  10.2174/1570180814666170505120258

文献信息

• Enantioselective Michael reaction of malonates and chalcones by phase-transfer catalysis using chiral quaternary ammonium salt
  作者：Dae Young Kim、Sun Chul Huh、Sung Min Kim

  DOI：10.1016/s0040-4039(01)01237-0

  日期：2001.9

  The catalytic enantioselective Michael reaction promoted by quaternary ammonium salt from cinchonidine as a phase-transfer catalyst is described. Treatment of malonate with chalcone derivatives under mild reaction conditions afforded the corresponding Michael adducts in good yields with good to moderate enantiomeric excesses.

  描述了由辛可尼丁作为相转移催化剂的季铵盐促进的催化对映选择性迈克尔反应。在温和的反应条件下用查耳酮衍生物处理丙二酸酯，得到相应的迈克尔加合物，收率高，对映体过量至中度。
• Enantioselective Michael reaction of nitroalkanes and chalcones by phase-transfer catalysis using chiral quaternary ammonium salts
  作者：Dae Young Kim、Sun Chul Huh

  DOI：10.1016/s0040-4020(01)00891-2

  日期：2001.10

  The catalytic enantioselective Michael reaction promoted by quaternary ammonium salt from cinchonidine as a phase transfer catalyst is described. Treatment of nitroalkanes with chalcone derivatives under mild reaction conditions afforded the corresponding Michael adducts in good yields with good to moderate enantiomeric excesses.

  描述了由辛可尼丁作为相转移催化剂的季铵盐促进的催化对映选择性迈克尔反应。在温和的反应条件下用查耳酮衍生物处理硝基烷，以高收率得到适量对映体过量的相应迈克尔加合物。
• 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.
• Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA
  作者：Louise Domeneghini Chiaradia、Alessandra Mascarello、Marcela Purificação、Javier Vernal、Marlon Norberto Sechini Cordeiro、María Emilia Zenteno、Andréa Villarino、Ricardo José Nunes、Rosendo Augusto Yunes、Hernán Terenzi

  DOI：10.1016/j.bmcl.2008.09.105

  日期：2008.12

  In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were obtained by aldolic condensation between aldehydes and acetophenones, under basic conditions. Five compounds presented moderate or good activity. The structure - activity analysis reveals that the predominant factor for the activity is the molecule planarity/hydrophobicity and the nature of the substituents. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of apoptotic chalcone analogues in HepG2 human hepatocellular carcinoma cells
  作者：Cheon-Soo Park、Yongchel Ahn、Dahae Lee、Sung Won Moon、Ki Hyun Kim、Noriko Yamabe、Gwi Seo Hwang、Hyuk Jai Jang、Heesu Lee、Ki Sung Kang、Jae Wook Lee

  DOI：10.1016/j.bmcl.2015.10.093

  日期：2015.12

  Eight chalcone analogues were prepared and evaluated for their cytotoxic effects in human hepatoma HepG2 cells. Compound 5 had a potent cytotoxic effect. The percentage of apoptotic cells was significantly higher in compound 5-treated cells than in control cells. Exposure to compound 5 for 24 h induced cleavage of caspase-8 and -3, and poly (ADP-ribose) polymerase (PARP). Our findings suggest that compound 5 is the active chalcone analogue that contributes to cell death in HepG2 cells via the extrinsic apoptotic pathway. (C) 2015 Elsevier Ltd. All rights reserved.