1-(4-bromophenyl)-3-(naphthalene-6-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: 1-(4-bromophenyl)-3-(naphthalene-6-yl)prop-2-en-1-one
• 英文别名: 1--3-<4-bromphenyl>-propen-(1)-on-(3)；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-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-3-(naphthalene-6-yl)prop-2-en-1-one 在 溶剂黄146 、 锌 作用下， 生成 1-<4-Cyanophenyl>-3--propanon-(1)
  参考文献：
  名称：

  Wagner; Voigt, Pharmazie, 1976, vol. 31, # 6, p. 354 - 360

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴苯乙酮 、 2-萘甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以93.91%的产率得到1-(4-bromophenyl)-3-(naphthalene-6-yl)prop-2-en-1-one
  参考文献：
  名称：

  查尔酮衍生物的合成、晶体结构、光谱和非线性光学性质：结合实验和理论研究

  摘要：

  摘要 以乙醇钠为碱，对溴苯乙酮与各种取代芳香醛在乙醇中反应制备了一组查耳酮化合物。合成的分子使用光谱技术如 UV-Vis、傅立叶变换红外 (FT-IR) 和核磁共振 (1H & 13C) 光谱学进行了很好的表征。在单晶 X 射线衍射仪上衍射这些化合物后，化合物被结晶并确认其最终结构。将光谱和分子信息与通过密度泛函理论 (DFT) 计算的模拟特性进行比较。所有查尔酮化合物的几何结构都已通过密度泛函理论 (DFT) 在 B3LYP 级别与 6-311 + G(d,p) 基组组合进行了优化。分别使用时间相关的 TD/DFT/B3LYP/6-311 + G(d,p) 和 B3LYP/6-311 + G(d,p) 水平报告了关于查耳酮衍生物的 UV-Vis 和 FT-IR 光谱的理论研究. 目前的研究表明，理论发现补充了实验结果。计算查耳酮系统的非线性光学特性，以深入了解将这些化合物设计为 NLO 材料的可能性。研究结果表明，除

  DOI：

  10.1016/j.molstruc.2017.03.090

文献信息

• Induction of apoptosis and cell cycle arrest in L-1210 murine lymphoblastic leukaemia cells by (2<i>E</i>)-3-(2-naphthyl)-1-(3′-methoxy-4′-hydroxy-phenyl)-2-propen-1-one
  作者：Fernanda Spezia Pedrini、Louise Domeneghini Chiaradia、Marley Aparecida Licínio、Ana Carolina Rabello De Moraes、Juliana Costa Curta、Aline Costa、Alessandra Mascarello、Tânia Beatriz Creczinsky-Pasa、Ricardo José Nunes、Rosendo Augusto Yunes、Maria Cláudia Santos-Silva

  DOI：10.1111/j.2042-7158.2010.01141.x

  日期：2010.8.2

  New compounds with biological targets and less cytotoxicity to normal cells are necessary for cancer therapy. In this work ten synthetic chalcones derived from 2-naphtaldehyde were evaluated for their cytotoxic effect in murine acute lymphoblastic leukemia cells L-1210.

  A series of ten chalcones derived from 2-naphtaldehyde and corresponding acetophenones were prepared by aldolic condensation, using methanol as solvent under basic conditions, at room temperature for 24 h. The cell viability was determined by MTT colorimeter method. The cell cycle phase analysis was carried out by flow cytometry after propidium iodide staining. The apoptosis induction was assessed by exposure to phosphatidylserine (ANNEXIN V-FITC). Cytometric analysis was performed to evaluate the expression of p53, Bcl-2 and Bax protein. The caspase-3 expression was studied by immunoblotting analysis.

  A preliminary screening of a series of ten chalcones derived from 2-naphtaldehyde showed that chalcone 8, (2E)-3-(2-naphtyl)-1-(3′-methoxy-4′-hydroxy-phenyl)-2-propen-1-one, had the highest cytotoxic effect (IC50 of 54 µm), but not in normal human lymphocytes. To better understand the cytotoxic mechanism of chalcone 8, its effect on cell cycle and apoptosis was assessed. Our results showed that chalcone 8 caused cell cycle arrest in the G2/M phase and a significant increase in the proportion of cells in the subG0/G1 phase. Our results also demonstrated that chalcone 8 promoted a modification in Bax : Bcl-2 ratio and increased p53 expression and caspase-3 activation.

  The studied chalcone 8 has cytotoxic effect against L-1210 lymphoblastic leukaemic cells, and this effect is associated with increase of p-53 and Bax expression.

  对于癌症治疗，需要具有生物靶点且对正常细胞毒性较小的新化合物。本研究评估了从2-萘醛衍生的十种合成查尔酮对小鼠急性淋巴细胞白血病细胞L-1210的细胞毒性作用。

  通过用甲醇作为溶剂，在基础条件下，于室温下进行24小时的醛缩反应，制备了十种从2-萘醛和相应的苯乙酮衍生的查尔酮。细胞活力通过MTT比色法确定。细胞周期分析通过丙磷碘化物染色后的流式细胞术进行。通过暴露于磷脂酰丝氨酸（ANNEXIN V-FITC）评估凋亡诱导。通过细胞仪分析评估p53、Bcl-2和Bax蛋白的表达。通过免疫印迹分析研究caspase-3的表达。

  对从2-萘醛衍生的十种查尔酮进行初步筛选显示，查尔酮8，(2E)-3-(2-萘基)-1-(3′-甲氧基-4′-羟基苯基)-2-丙烯-1-酮，具有最高的细胞毒性作用（IC50为54 µm），但对正常人淋巴细胞无影响。为了更好地理解查尔酮8的细胞毒性机制，评估了其对细胞周期和凋亡的影响。我们的结果显示，查尔酮8导致细胞周期在G2/M期的停滞，并显著增加了处于亚G0/G1期的细胞比例。我们的结果还表明，查尔酮8促进了Bax:Bcl-2比率的改变，增加了p53的表达和caspase-3的活化。

  研究的查尔酮8对L-1210淋巴细胞白血病细胞具有细胞毒性作用，这种作用与p-53和Bax表达的增加有关。

• Design, Synthesis and Biological Evaluation of Benzohydrazide Derivatives Containing Dihydropyrazoles as Potential EGFR Kinase Inhibitors
  作者：Hai-Chao Wang、Xiao-Qiang Yan、Tian-Long Yan、Hong-Xia Li、Zhong-Chang Wang、Hai-Liang Zhu

  DOI：10.3390/molecules21081012

  日期：——

  A series of novel benzohydrazide derivatives containing dihydropyrazoles have been synthesized as potential epidermal growth factor receptor (EGFR) kinase inhibitors and their biological activities as potential antiproliferative agents have been evaluated. Among these compounds, compound H20 exhibited the most potent antiproliferative activity against four cancer cell line variants (A549, MCF-7, HeLa

  已经合成了一系列含有二氢吡唑的新型苯并酰肼衍生物作为潜在的表皮生长因子受体（EGFR）激酶抑制剂，并评估了它们作为潜在的抗增殖剂的生物学活性。在这些化合物中，化合物H20对四种癌细胞系变体（A549，MCF-7，HeLa，HepG2）表现出最强的抗增殖活性，IC50值分别为0.46、0.29、0.15和0.21μM，显示出最强的EGFR抑制作用活性（EGFR的IC50 = 0.08μM）。为了预测这些苯并酰肼衍生物的生物活性和活性关系（SAR），进行了分子模型模拟研究。这些结果表明，化合物H20可能是有前途的抗癌药。
• Synthesis and biological evaluation of compounds which contain pyrazole, thiazole and naphthalene ring as antitumor agents
  作者：Ji-Wen Yuan、She-Feng Wang、Zhong-Liang Luo、Han-Yue Qiu、Peng-Fei Wang、Xin Zhang、Yong-An Yang、Yong Yin、Fei Zhang、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2014.03.072

  日期：2014.5

  A series of compounds which contain pyrazole, thiazole and naphthalene ring (1a-7a, 1b-7b, 1c-7c, 1d-7d) were firstly synthesized and their anti-proliferative activity, EGFR inhibitory activity, cytotoxicity and inhibition to Hela cell migration were evaluated. Compound 2-(3-(3,4-dimethylphenyl)-5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl) thiazol-4(5H)-one (7d) displayed the most potent inhibitory activity (IC50 = 0.86 mu M for Hela and IC50 = 0.12 mu M for EGFR). Structure-activity relationship (SAR) analysis showed that the anti-proliferative activity was affected by A-ring-substituent (-OCH3 > -CH3 > -H > -Br > -Cl > -F). Docking simulation of compound 7d into EGFR active site showed that naphthalene ring of 7d with LYS721 formed two p-pi bonds, which enhanced antitumor activity. Therefore, compound 7d may be developed as a potential antitumor agent. (C) 2014 Elsevier Ltd. All rights reserved.