(E)-1-(4-methoxyphenyl)-3-(naphthalen-2-yl)prop-2-en-1-one

• 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-methoxyphenyl)-3-(naphthalen-2-yl)prop-2-en-1-one
• 英文别名: (E)-1-(4-methoxyphenyl)-3-naphthalen-2-ylprop-2-en-1-one
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: WXTCAWIUBANCFK-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-methoxyphenyl)-3-(naphthalen-2-yl)prop-2-en-1-one 在 N-溴代丁二酰亚胺(NBS) 、 碘苯二乙酸 、 C₄₅H₂₉F₃NO₅PS 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 (R)-N-(6-methoxy-3-(4-methoxyphenyl)-1-(naphthalen-2-yl)-1H-inden-2-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  手性布朗斯台德酸催化芳基和 2-噻吩乙烯醇的对映选择性脱水纳扎罗夫型电环化

  摘要：

  描述了一种有效的手性 Brønsted 酸催化的对映选择性脱水纳扎罗夫型电环化 (DNE) 的富电子芳基-和 2-噻吩基-β-氨基-2-en-1-ols。4π 旋转电环化反应可以以高达 99% 的优异收率和高达 99% 的对映体过量 (ee) 值获得各种相应的 1 H-茚和 4 H-环戊二烯 [b] 噻吩。基于提议的密切接触离子对物种的实验和计算研究，进一步由底物阳离子的氨基和手性催化剂阴离子之间的氢键辅助，提供了对观察到的产物对映选择性的深入了解。

  DOI：

  10.1021/jacs.8b02339
• 作为产物：
  描述：

  2-萘甲醛 、 对甲氧基苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以89.9 %的产率得到(E)-1-(4-methoxyphenyl)-3-(naphthalen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  作为有效的口服活性 hCYP3A4 抑制剂的查耳酮衍生物的设计、合成和生物学评价

  摘要：

  人细胞色素 P450 3A4 (hCYP3A4) 是最重要的药物代谢酶之一，催化约50% 治疗药物的代谢清除。CYP3A4抑制剂已被用于提高hCYP3A4底物药物的体内功效。然而，大多数现有的hCYP3A4抑制剂可能会引发严重的副作用或对内源代谢产生不良影响。本研究旨在从查耳酮衍生物中发现有效的口服活性 hCYP3A4 抑制剂，并在体外和体内测试其抗 hCYP3A4 作用。经过三轮筛选和结构优化，发现异喹啉查尔酮类化合物具有优异的抗hCYP3A4作用。SAR 研究表明，在 A 环上引入异喹啉环可显着增强抗 CYP3A4 作用，产生A10 (IC 50  = 102.10 nM) 作为一种有前途的先导化合物。第二轮SAR研究表明，在B环羰基对位引入取代基可显着提高抗CYP3A4效果。结果，C6被确定为人肝微粒体 (HLM) 中最有效的 hCYP3A4 抑制剂 (IC 50  = 43.93

  DOI：

  10.1016/j.bmcl.2023.129435

文献信息

• Orchestrating a β-Hydride Elimination Pathway in Palladium(II)-Catalyzed Arylation/Alkenylation of Cyclopropanols Using Organoboron Reagents
  作者：Thangeswaran Ramar、Murugaiah A. M. Subbaiah、Andivelu Ilangovan

  DOI：10.1021/acs.joc.1c02735

  日期：2022.4.1

  scope of chemoselective β-hydride elimination in the context of arylation/alkenylation of homoenolates from cyclopropanol precursors using organoboronic reagents as transmetalation coupling partners was examined. The reaction optimization paradigm revealed a simple ligand-free Pd(II) catalytic system to be most efficient under open air conditions. The preparative scope, which was investigated with

  在使用有机硼试剂作为金属转移偶联剂对环丙醇前体的高烯醇化物进行芳基化/烯基化的情况下，化学选择性 β-氢化物消除的范围进行了研究。反应优化范式揭示了一个简单的无配体 Pd(II) 催化体系在露天条件下最有效。用 48 个例子研究了制备范围，支持该反应适用于广泛的可耐受各种官能团的底物，同时以 62-95% 的产率提供 β-取代的烯酮和二烯酮衍生物。
• 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.
• Synthesis of Renoprotective Chalcone Analogues That Protect Against Cisplatin-induced Cytotoxicity in LLC-PK1 Cells
  作者：Noriko Yamabe、Dahae Lee、Heesu Lee、Myung Sook Shin、Gwi Seo Hwang、Ki Sung Kang、Jae Wook Lee

  DOI：10.1002/bkcs.10984

  日期：2016.11
• 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.
• Chalcones with electron-withdrawing and electron-donating substituents: Anticancer activity against TRAIL resistant cancer cells, structure–activity relationship analysis and regulation of apoptotic proteins
  作者：Chun Wai Mai、Marzieh Yaeghoobi、Noorsaadah Abd-Rahman、Yew Beng Kang、Mallikarjuna Rao Pichika

  DOI：10.1016/j.ejmech.2014.03.002

  日期：2014.4

  In the present study, a series of 46 chalcones were synthesised and evaluated for antiproliferative activities against the human TRAIL-resistant breast (MCF-7, MDA-MB-231), cervical (HeLa), ovarian (Caov-3), lung (A549), liver (HepG2), colorectal (HT-29), nasopharyngeal (CNE-1), erythromyeloblastoid (K-562) and T-Iymphoblastoid (CEM-SS) cancer cells. The chalcone 38 containing an amino (-NH2) group on ring A was the most potent and selective against cancer cells. The effects of the chalcone 38 on regulation of 43 apoptosis-related markers in HT-29 cells were determined. The results showed that 20 apoptotic markers (Bad, Bax, BcI-2, Bcl-w, Bid, Bim, CD40, Fas, HSP27, IGF-1, IGFBP-4, IGFBP-5, Livin, p21, Survivin, 5TNE-R2, TRAIL-R2, XIAP, caspase-3 and caspase-8) were either up regulated or down regulated. (C) 2014 Elsevier Masson SAS.All rights reserved.