1-(4-methoxy-phenyl)-3-(2-prop-2-ynyloxy-phenyl)-propenone | 1227420-42-9

• 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-methoxy-phenyl)-3-(2-prop-2-ynyloxy-phenyl)-propenone
• 英文别名: 1-(4-methoxyphenyl)-3-(2-prop-2-ynoxyphenyl)prop-2-en-1-one
• CAS: 1227420-42-9
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: LDBKMFQLVKTGQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-methoxy-phenyl)-3-(2-prop-2-ynyloxy-phenyl)-propenone 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 一水合肼 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(3-(4-methoxyphenyl)-5-(2-((1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methoxy) phenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis, characterization, α-glucosidase inhibition and molecular modeling studies of some pyrazoline-1H-1,2,3-triazole hybrids

  摘要：

  A series of molecular hybrids based on pyrazoline and 1,2,3-triazole pharmacophores were designed and synthesized as antidiabetic agents. The structures of all the derivatives were con fi rmed using H-1 NMR, C-13 NMR and HRMS. Moreover, the structure of one of the intermediate precursor was con fi rmed using single crystal X-ray diffraction. The anti-diabetic potential of all the synthesized compounds was explored in terms of a-glucosidase inhibition studies. All the compounds exhibited remarkable inhibition of a-glucosidase. The inhibition of enzyme by compound TPZ2 (IC50 = 41.29 +/- 0.123) and TPZ8 (IC50 = 47.94 +/- 0.246) was found to be more promising as compared to the reference drug i.e., Acarbose (IC50= 60.68 +/- 0.123). The inhibition of a-glucosidase was further supported by in silico docking studies. In order to explore the most favorable binding interactions the binding pose of lowest energy was then subjected to molecular dynamics studies. Both the ligands have reasonable interactions with the protein active site with average interaction energy of- 270.88 kcal/mol and- 273.90 kcal/mol for TPZ8 and TPZ2 , respectively. (C) 2020 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2020.128253
• 作为产物：
  描述：

  水杨醛 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-(4-methoxy-phenyl)-3-(2-prop-2-ynyloxy-phenyl)-propenone
  参考文献：
  名称：

  通过偶氮甲碱叶立德的[3 + 2]环加成反应区域选择性和立体选择性合成螺吡咯烷-羟吲哚和双螺吡咯烷-羟吲哚接枝大环化合物

  摘要：

  通过偶氮甲碱叶立德的分子内和分子间 [3 + 2] 环加成，实现了一种方便有效的区域选择性大环化三唑桥联螺吡咯烷-羟吲哚和双-螺吡咯烷-羟吲哚衍生物的方法。点击反应所需的查尔酮靛红前体9a-i由 N-烷基叠氮靛红4和炔丙基氧基查耳酮8a-i的反应获得，后者又通过炔丙基氧基水杨醛6和取代的甲基酮7a-i的羟醛缩合获得. 环加合物的区域和立体化学结果基于 2D NMR 确定，并通过单晶 XRD 分析确认。高效率、温和的反应条件、高区域和立体选择性、原子经济性和操作简单是所采用的大环化过程的典型优势。

  DOI：

  10.1039/c9ra10463a

文献信息

• Synthesis, antimalarial and antitubercular activity of acetylenic chalcones
  作者：Renate H. Hans、Eric M. Guantai、Carmen Lategan、Peter J. Smith、Baojie Wan、Scott G. Franzblau、Jiri Gut、Philip J. Rosenthal、Kelly Chibale

  DOI：10.1016/j.bmcl.2009.12.062

  日期：2010.2

  A series of acetylenic chalcones were evaluated for antimalarial and antitubercular activity. The antimalarial data for this series suggests that growth inhibition of the W2 strain of Plasmodium falciparum can be imparted by the introduction of a methoxy group ortho to the acetylenic group. Most compounds were more active against non-replicating than replicating cultures of Mycobacterium tuberculosis

  评估了一系列炔属查耳酮的抗疟和抗结核活性。该系列的抗疟数据表明，恶性疟原虫W2菌株的生长抑制可通过在炔基上邻位引入甲氧基来实现。与结核分枝杆菌H 37 Rv的复制培养相比，大多数化合物对非复制的活性更高，这对现有的抗结核病药物而言是不同寻常的模式。
• Fabrication of silicon embedded isomeric chalcone linkers using [CuBr(PPh3)3]
  作者：Gurjaspreet Singh、Jasbhinder Singh、Gurpreet Kaur、Jandeep Singh

  DOI：10.1016/j.poly.2016.10.001

  日期：2017.3

  The positional isomeric units of substituted chalcones were synthesized using [CuBr(PPh3)(3)] as source of catalyst. The alkynes (1a-9a) were fabricated with azides resulting into triazole moiety containing triethoxysilane substituents (1b-9b) which were further converted into silatranes 1c-9c. The synthesized compounds were confirmed by spectroscopic analytical studies like NMR (1H, 13C), IR, mass recognition studies confirm the silatrane product formation. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis, characterization, α-glucosidase inhibition and molecular modeling studies of some pyrazoline-1H-1,2,3-triazole hybrids
  作者：Lokesh Kumar、Kashmiri Lal、Pinki Yadav、Ashwani Kumar、Avijit Kumar Paul

  DOI：10.1016/j.molstruc.2020.128253

  日期：2020.9

  A series of molecular hybrids based on pyrazoline and 1,2,3-triazole pharmacophores were designed and synthesized as antidiabetic agents. The structures of all the derivatives were con fi rmed using H-1 NMR, C-13 NMR and HRMS. Moreover, the structure of one of the intermediate precursor was con fi rmed using single crystal X-ray diffraction. The anti-diabetic potential of all the synthesized compounds was explored in terms of a-glucosidase inhibition studies. All the compounds exhibited remarkable inhibition of a-glucosidase. The inhibition of enzyme by compound TPZ2 (IC50 = 41.29 +/- 0.123) and TPZ8 (IC50 = 47.94 +/- 0.246) was found to be more promising as compared to the reference drug i.e., Acarbose (IC50= 60.68 +/- 0.123). The inhibition of a-glucosidase was further supported by in silico docking studies. In order to explore the most favorable binding interactions the binding pose of lowest energy was then subjected to molecular dynamics studies. Both the ligands have reasonable interactions with the protein active site with average interaction energy of- 270.88 kcal/mol and- 273.90 kcal/mol for TPZ8 and TPZ2 , respectively. (C) 2020 Elsevier B.V. All rights reserved.
• Regio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides
  作者：Perumal Prabhakaran、Perumal Rajakumar

  DOI：10.1039/c9ra10463a

  日期：——

  through intra and self-intermolecular [3 + 2] cycloaddition of azomethine ylides. The chalcone isatin precursors 9a–i required for the click reaction were obtained from the reaction of N-alkylazidoisatin 4 and propargyloxy chalcone 8a–i which in turn were obtained by the aldol condensation of propargyloxy salicylaldehyde 6 and substituted methyl ketones 7a–i. The regio- and stereochemical outcome of the

  通过偶氮甲碱叶立德的分子内和分子间 [3 + 2] 环加成，实现了一种方便有效的区域选择性大环化三唑桥联螺吡咯烷-羟吲哚和双-螺吡咯烷-羟吲哚衍生物的方法。点击反应所需的查尔酮靛红前体9a-i由 N-烷基叠氮靛红4和炔丙基氧基查耳酮8a-i的反应获得，后者又通过炔丙基氧基水杨醛6和取代的甲基酮7a-i的羟醛缩合获得. 环加合物的区域和立体化学结果基于 2D NMR 确定，并通过单晶 XRD 分析确认。高效率、温和的反应条件、高区域和立体选择性、原子经济性和操作简单是所采用的大环化过程的典型优势。