(E)-3-(4-methoxyphenyl)-1-(4-(prop-2-yn-1-yloxy)phenyl)prop-2-en-1-one | 1217264-22-6

• 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)-3-(4-methoxyphenyl)-1-(4-(prop-2-yn-1-yloxy)phenyl)prop-2-en-1-one
• 英文别名: (E)-3-(4-methoxyphenyl)-1-(4-prop-2-ynoxyphenyl)prop-2-en-1-one
• CAS: 1217264-22-6
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: FGYVUELBKKTFMB-AWNIVKPZSA-N

物化性质

• 沸点：
  474.6±45.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-methoxyphenyl)-1-(4-(prop-2-yn-1-yloxy)phenyl)prop-2-en-1-one 在 copper(ll) sulfate pentahydrate 、 sodium methylate 、 sodium ascorbate 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 (E)-3-(4-methoxyphenyl)-1-[4-[[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]triazol-4-yl]methoxy]phenyl]prop-2-en-1-one
  参考文献：
  名称：

  新型糖基化的1,4-取代的三唑基卤代酮衍生物的抗癌潜力。

  摘要：

  使用d-葡糖基叠氮化合物的1,3-环加成（Click chemistry）与各种炔丙基化查尔酮衍生物，然后合成一系列糖基化的1,4-取代的三唑查尔酮衍生物（8a-f和14a-r）。去-O-乙酰化。评价合成的化合物对人乳腺癌细胞系和非癌细胞的细胞毒性潜力。MTT测定法鉴定了三种有希望的细胞毒性化合物（14c，14i和14l），并用活性化合物中最佳的化合物14i进行了进一步的生化和显微镜研究。

  DOI：

  10.1016/j.bmcl.2019.08.019
• 作为产物：
  描述：

  对羟基苯乙酮 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-3-(4-methoxyphenyl)-1-(4-(prop-2-yn-1-yloxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  新型查尔酮和酰胺连接的 1,4-二取代 1,2,3 三唑的抗菌和计算机评价

  摘要：

  报道了一系列十二个含查尔酮酰胺连接的 1,4-二取代 1,2,3-三唑杂化物及其炔烃前体的设计、合成、光谱表征和抗菌评估。与查尔酮连接的末端炔烃前体 (0.8552-0.16270 μmol/mL) 相比，三唑杂化物对测试的细菌和真菌菌株表现出低得多的 MIC 值 (0.0285-0.01182 μmol/mL)，从而通过结合三种药效团显示出协同抗菌作用单位，查尔酮、酰胺和1,2,3-三唑。对接和分子动力学 (MD) 研究通过蛋白质-配体复合物的各种结合相互作用和稳定性进一步支持了这些杂合体的抗菌潜力。药物相似性也通过计算机预测ADME 和毒性研究。

  DOI：

  10.1016/j.molstruc.2022.132632

文献信息

• Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners
  作者：Mohamed Ramadan El Sayed Aly、Hosam Ali Saad、Shams Hashim Abdel-Hafez

  DOI：10.3762/bjoc.11.208

  日期：——

  3β-Azidocholest-5-ene (3) and (3β)-3-(prop-2-yn-1-yloxy)cholest-5-ene (10) were prepared as substrates to synthesize a variety of three-motif pharmacophoric conjugates through CuAAC. Basically, these conjugates included cholesterol and 1,2,3-triazole moieties, while the third, the pharmacophore, was either a chalcone, a lipophilic residue or a carbohydrate tag. These compounds were successfully prepared in good yields and characterized by NMR, MS and IR spectroscopic techniques. Chalcone conjugate 6c showed the best antimicrobial activity, while the lactoside conjugate 27 showed the best cytotoxic effect in vitro.

  3β-氮杂胆甾-5-烯（3）和（3β）-3-(丙-2-炔-1-氧基)胆甾-5-烯（10）被制备为底物，以合成各种三基团药效团结合物通过CuAAC。基本上，这些结合物包括胆固醇和1,2,3-三唑基团，而第三个药效团则是香豆素、疏水残基或碳水化合物标记中的一个。这些化合物以良好的产率成功制备，并通过NMR、MS和IR光谱技术进行表征。香豆素结合物6c显示出最佳的抗微生物活性，而乳糖苷结合物27在体外显示出最佳的细胞毒作用。
• Synthesis, Biological Evaluation and Molecular Modeling Studies of Propargyl-Containing 2,4,6-Trisubstituted Pyrimidine Derivatives as Potential Anti-Parkinson Agents
  作者：Bhupinder Kumar、Mohit Kumar、Ashish Ranjan Dwivedi、Vinod Kumar

  DOI：10.1002/cmdc.201700589

  日期：2018.4.6

  Monoamine oxidase B (MAO‐B) inhibitors are potential drug candidates for the treatment of various neurological disorders including Parkinson's disease. A total of 20 new propargyl‐containing 2,4,6‐trisubstituted pyrimidine derivatives were synthesized and screened for MAO inhibition using Amplex Red assays. All the synthesized compounds were found to be reversible and selective inhibitors of the MAO‐B

  单胺氧化酶B（MAO-B）抑制剂是潜在的候选药物，可用于治疗包括帕金森氏症在内的各种神经系统疾病。总共合成了20种新的含炔丙基的2,4,6-三取代嘧啶衍生物，并使用Amplex Red分析筛选了MAO抑制作用。发现所有合成的化合物都是亚微摩尔浓度的MAO-B亚型的可逆和选择性抑制剂。MVB3是最有效的MAO-B抑制剂，其IC 50为0.38±0.02μ值μ，而MVB6（IC 50 = 0.51±0.04μ μ）和MVB16（IC 50 = 0.48±0.06μ μ）对MAO-B的选择性最高，选择性指数超过100倍。在细胞毒性研究中，发现这些化合物是无毒的，以人神经母SH-SY5Y细胞在25μ浓度米。MVB6被发现在10μ活性氧物种的细胞内水平降低至68％米浓度，而其他的化合物不产生活性氧水平显著变化。在分子建模研究中，MVB3对MAO-B同工型显示出很强的结合亲和力，对接得分为−10.45
• Design, synthesis and anticancer activity of matrine–1H-1,2,3-triazole–chalcone conjugates
  作者：Lihui Zhao、Lina Mao、Ge Hong、Xiaojiao Yang、Tianjun Liu

  DOI：10.1016/j.bmcl.2015.04.051

  日期：2015.6

  A series of novel matrine–1H-1,2,3-triazole–chalcone conjugates was synthesized and their anticancer activity against A549, Bel-7402, Hela, and MCF-7 cancer cells was evaluated. Most of the conjugates displayed higher potency than their components. Compounds 6h and 6i exhibited more potent anticancer activity than 5-fluorouracil against the four tested human cancer cell lines and lower cytotoxicity

  合成了一系列新型苦参碱-1 H -1,2,3-三唑-查耳酮缀合物，并评估了它们对A549，Bel-7402，Hela和MCF-7癌细胞的抗癌活性。大多数缀合物显示出比其组分更高的效价。与5-氟尿嘧啶相比，化合物6h和6i对四种测试的人类癌细胞系表现出更强的抗癌活性，并且对NIH3T3正常细胞的细胞毒性较低。流式细胞仪测试表明化合物6h可以以浓度依赖的方式诱导A549细胞凋亡。此外，6h可以有效抑制小鼠异种移植模型中人肿瘤的生长，而不会引起明显的毒性。
• Click reaction based synthesis, antimicrobial, and cytotoxic activities of new 1,2,3-triazoles
  作者：Mohamed Ramadan El Sayed Aly、Hosam Ali Saad、Mosselhi Abdelnabi Mosselhi Mohamed

  DOI：10.1016/j.bmcl.2015.04.096

  日期：2015.7

  Three-motif pharmacophoric models 20a-e and 21-25 were prepared in good yields by CuAAC of two azido substrates 2 and 11 with seven terminal acetylenic derivatives including chalcones 17a-e, theophylline 18 and cholesterol 19. The structure of these compounds was elucidated by NMR, MS, IR spectroscopy and micro analyses. This series was screened as antimicrobial and cytotoxic agents in vitro. Most derivatives showed appreciable antibacterial activity, but they displayed weak cytotoxic, and antifungal activities. Notably, conjugate 25 (cream of the crop) was found to be more active than Ampicillin against Escherichia coli and Staphylococcus aureus and showed appreciable antifungal and cytotoxic activities as well. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthetic investigations and photo-physical properties of 1,2,3-triazole encapped chalconyl substituted organotriethoxysilanes
  作者：Gurjaspreet Singh、Aanchal Arora、Satinderpal Singh Mangat、Jandeep Singh、Sunita Rani、Navneet Kaur

  DOI：10.1016/j.jorganchem.2014.11.022

  日期：2015.2

  Organotriethoxysilanes (OTES) play an impressive role in the designing of organic-inorganic hybrid materials. The highly efficient copper catalysed 'Click Silylation' is followed for the functionalization of 3-azidopropyltriethoxysilane (AzPTES) with a series of acetylinic chalcones. Chalcones being ubiquitous subunits present in various natural products possess a wide variety of biological activities and are thus considered for the synthesis of new hybrid templates. Twenty one new chalcone holding triazole encapped OTES were synthesized in quantitative yields. All the synthesized compounds were well characterized by IR, H-1 and C-13 NMR spectroscopic techniques. The photo-physical properties of all the OTES were compared and the effect of different substitutions was explicated. These OTES can be put to amazing applications in the field of medicine and material chemistry. (C) 2014 Elsevier B.V. All rights reserved.