1-(4-methoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one | 56412-54-5

• 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-methoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one
• 英文别名: 1-(4-Methoxylphenyl)-3-(naphthalen-1-yl)-2-propen-1-one；1-(4-methoxyphenyl)-3-naphthalen-1-ylprop-2-en-1-one
• CAS: 56412-54-5
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: QUCMFZOJKRASJO-UHFFFAOYSA-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：

  1-(4-methoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one 在 sodium acetate 、 乙酸酐 、 potassium hydroxide 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 2-(3-(4-methoxyphenyl)-5-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazole
  参考文献：
  名称：

  Synthesis and biological evaluation of compounds which contain pyrazole, thiazole and naphthalene ring as antitumor agents

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.03.072
• 作为产物：
  描述：

  1-萘甲醛 、 对甲氧基苯乙酮 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1-(4-methoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one
  参考文献：
  名称：

  2,4-二芳基-嘧啶并[1,2-a]苯并咪唑衍生物作为具有有效抗白血病活性的新型抗癌药物：合成、生物学评价和激酶分析

  摘要：

  急性髓系白血病 (AML) 是最具侵袭性的人类癌症之一，发展迅速，因此需要立即治疗。在目前的研究中，报道了作为潜在抗 AML 药物的新型嘧啶并[1,2- a ]苯并咪唑 ( 5a-p )衍生物的开发。在NCI-DTP中检查制备的化合物5a-p的体外抗肿瘤活性，随后选择5h进行全组五剂量筛选以评估其TGI、LC 50和GI 50值。化合物5h在低微摩尔浓度下对所有测试的人类癌细胞系均表现出有效的抗肿瘤活性，GI 50范围为 0.35 至 9.43 μM，对白血病具有优异的亚微摩尔浓度。此外，在一组人急性白血病细胞系（即 HL60、MOLM-13、MV4-11、CCRF-CEM 和 THP-1）上测试了嘧啶并[1,2- a ]苯并咪唑5e-l ，其中5e-h达到了单次所有测试细胞系的数字微摩尔 GI 50值。首先测试所有制备的化合物对白血病相关突变体 FLT3-ITD 以及 ABL、CDK2 和

  DOI：

  10.1016/j.ejmech.2023.115610

文献信息

• Design, synthesis, in silico studies, and evaluation of novel chalcones and their pyrazoline derivatives for antibacterial and antitubercular activities
  作者：Shivani Pola、Karan Kumar Banoth、Murugesan Sankaranarayanan、Ramesh Ummani、Achaiah Garlapati

  DOI：10.1007/s00044-020-02602-8

  日期：2020.10

  chalcones (3a–3p) and their pyrazoline derivatives (4a–4h) were synthesized using substituted acetophenones, substituted naphthaldehydes, and hydrazine hydrate as starting materials. All the synthesized compounds were characterized by IR, NMR, and mass spectrometric analysis and screened for antimycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC 27924) and antibacterial activity against

  以取代的苯乙酮，取代的萘乙醛和水合肼为起始原料合成了一系列新的萘基查耳酮（3a - 3p）及其吡唑啉衍生物（4a - 4h）。所有合成的化合物均通过IR，NMR和质谱分析进行表征，并筛选出针对结核分枝杆菌H37Rv（ATCC 27924）的抗分枝杆菌活性和对金黄色葡萄球菌（MTCC 96），枯草芽孢杆菌（MTCC 441），大肠杆菌（MTCC ）的抗菌活性443）和克雷伯菌肺炎（MTCC 109）。化合物3b和3p对所有测试的细菌菌株显示出显着的抗菌活性。在合成的化合物中，在吡唑啉第3位具有2-羟基-5-溴苯基取代的化合物4b具有显着的抗分枝杆菌活性，MIC为6.25 µM，与标准异烟肼相当。进一步筛选合成的化合物对MDA-MB-231和SKOV3细胞系的细胞毒活性。化合物3a，3l，4b，4c，4e和4h不显示任何细胞毒性，其他化合物显示IC 50与标准阿霉素显示的1.20和1.30 µ
• Synthesis and biological effects of naphthalene-chalcone derivatives
  作者：Qing-Hao Jin、Hong-Hai Chen、Wen-Bo Chen、Zhi-Yang Fu、Li-Ping Guan、Hai-Ying Jiang

  DOI：10.1007/s00044-020-02525-4

  日期：2020.5

  In this paper, 21 naphthalene-chalcone derivatives were synthesized and their biological effects were evaluated. The results showed that compounds 2a–2u displayed clear antidepressant activity at 30 mg/kg in the forced swimming test. Compounds 2h, 2o, 2t, and 2u exhibited a good antidepressant effect in the forced swimming test and tail suspension test at 30 mg/kg. Compounds 2h, 2o, 2t, and 2u but

  本文合成了21种萘-查耳酮衍生物，并对其生物学效果进行了评价。结果表明，在强制游泳试验中，化合物2a–2u在30 mg / kg时显示出明显的抗抑郁活性。化合物2h，2o，2t和2u在30 mg / kg的强迫游泳试验和尾部悬吊试验中表现出良好的抗抑郁作用。化合物2h，2o，2t和2u在小鼠的野外试验中对运动能力没有影响。此外，化合物2o的最抗抑郁活性可能是由中枢神经系统中5-羟色胺和去甲肾上腺素水平升高介导的。化合物2a–2u在30 mg / kg时也显示出镇痛和抗炎作用。
• Tandem allylic oxidation–condensation/esterification catalyzed by silica gel: an expeditious approach towards antimalarial diaryldienones and enones from natural methoxylated phenylpropenes
  作者：Abhishek Sharma、Naina Sharma、Amit Shard、Rakesh Kumar、Dinesh Mohanakrishnan、Saima、Arun K. Sinha、Dinkar Sahal

  DOI：10.1039/c1ob05293d

  日期：——

  A new one-pot strategy has been developed, wherein abundantly available methoxylated phenylpropenes are directly transformed into corresponding dienones (1,5-diarylpenta-2,4-dien-1-ones) and enones (chalcones and cinnamic esters) via allylic oxidation–condensation or allylic oxidation–esterification sequences. Preliminary antimalarial activity studies of the above synthesized diaryldienones and enones against Plasmodium falciparum (Pf3D7) have shown them to be promising lead candidates for developing newer and economical antimalarial agents. In particular, two enones (12b and 13b) were found to possess comparatively better activity (IC50 = 4.0 and 3.4 μM, respectively) than licochalcone (IC50 = 4.1 μM), a well known natural antimalarial compound.

  开发了一种新的单锅法策略，利用丰富的甲氧基化苯丙烯类化合物，通过烯丙位氧化-缩合或烯丙位氧化-酯化序列，直接转化为相应的二烯酮（1,5-二芳基-2,4-戊二烯-1-酮）和烯酮（查耳酮和肉桂酸酯）。对上述合成的二芳基二烯酮和烯酮进行的初步抗疟活性研究表明，它们是开发新型经济抗疟药物的有希望的先导候选物。特别是，两个烯酮（12b和13b）的活性（IC50分别为4.0和3.4微摩尔）优于已知的天然抗疟化合物licochalcone（IC50=4.1微摩尔）。
• Regioselective Synthesis of 3,4-Disubstituted Isoxazoles by Using a Chalcone-Rearrangement Strategy
  作者：Tomohiro Maegawa、Akira Nakamura、Tohko Kine、Haruna Uenishi、Yuri Maki、Yasuhito Kase、Mayo Takagi

  DOI：10.1055/a-2028-9454

  日期：——

  We have developed a regioselective synthesis of 3,4-disubstituted isoxazoles by using a chalcone-rearrangement strategy. The reaction of β-ketoacetals with hydroxylamine hydrochloride and pyridine afforded the corresponding 3,4-disubstituted isoxazoles via isoxazolines or oximes. Depending on the substrate, another disubstituted isomer was also obtained under our optimized conditions, and a reaction

  我们通过使用查尔酮重排策略开发了 3,4-二取代异恶唑的区域选择性合成。β-酮缩醛与盐酸羟胺和吡啶反应通过异恶唑啉或肟得到相应的 3,4-二取代异恶唑。根据底物，在我们的优化条件下还获得了另一种双取代异构体，并提出了每种转化的反应机理。
• Sulfonamide derivatives containing dihydropyrazole moieties selectively and potently inhibit MMP-2/MMP-9: Design, synthesis, inhibitory activity and 3D-QSAR analysis
  作者：Xiao-Qiang Yan、Zhong-Chang Wang、Zhen Li、Peng-Fei Wang、Han-Yue Qiu、Long-Wang Chen、Xiao-Yuan Lu、Peng-Cheng Lv、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2015.08.026

  日期：2015.10

  New series of sulfonamide derivatives containing a dihydropyrazole moieties inhibitors of MMP-2/MMP-9 were discovered using structure-based drug design. Synthesis, antitumor activity, structure-activity relationship and optimization of physicochemical properties were described. In vitro the bioassay results revealed that most target compounds showed potent inhibitory activity in the enzymatic and cellular assays. Among the compounds, compound 3i exhibited the most potent inhibitory activity with IC50 values of 0.21 mu M inhibiting MMP-2 and 1.87 mu M inhibiting MMP-9, comparable to the control positive compound CMT-1 (1.26 mu M, 2.52 mu M). Docking simulation was performed to position compound 3i into the MMP-2 active site to determine the probable binding pose. Docking simulation was further performed to position compound 3i into the MMP-2 active site to determine the probable binding model the 3D-QSAR models were built for reasonable design of MMP-2/MMP-9 inhibitors at present and in future. (C) 2015 Elsevier Ltd. All rights reserved.