1-(4-methoxy-phenyl)-3-(4-prop-2-ynyloxy-phenyl)-propenone | 1227420-48-5

• 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-methoxy-phenyl)-3-(4-prop-2-ynyloxy-phenyl)-propenone
• 英文别名: 1-(4-methoxyphenyl)-3-(4-prop-2-ynoxyphenyl)prop-2-en-1-one
• CAS: 1227420-48-5
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: NGBWKHXKSQXKSS-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-(4-prop-2-ynyloxy-phenyl)-propenone 在 溴化三(三苯基磷)铜 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 9.0h， 生成 3-(4-(-(1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Fabrication of silicon embedded isomeric chalcone linkers using [CuBr(PPh3)3]

  摘要：

  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.

  DOI：

  10.1016/j.poly.2016.10.001
• 作为产物：
  描述：

  对羟基苯甲醛 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(4-methoxy-phenyl)-3-(4-prop-2-ynyloxy-phenyl)-propenone
  参考文献：
  名称：

  吡唑啉系 1,2,3-三唑：合成、抗菌评估和计算机研究

  摘要：

  使用吡唑啉连接的炔烃和2-溴-N-芳基乙酰胺之间的1,3-偶极环加成，明智地设计和合成了一系列新的吡唑啉-酰胺连接的1,2,3-三唑杂化物。所有新合成的化合物都针对不同的微生物菌株进行了体外评估，即。大肠杆菌、枯草芽孢杆菌、金黄色葡萄球菌、黑曲霉和白色念珠菌。吡唑啉连接的末端炔烃（4a-c）对不同细菌和真菌菌株的 MIC = 0.062-0.078 μmol/mL。然而，吡唑啉-酰胺连接的 1,2,3-三唑杂化物 ( 6a-6t ) 显示 MIC = 0.0229–0.050 μmol/mL。化合物6e表现出更好的抗大肠杆菌和两种真菌菌株与使用的标准药物相比。对细菌 DNA Gyr A 和真菌 14α-甾醇去甲基酶进行了最有效化合物的对接研究。还使用分子动力学模拟研究了4a和6e与靶标的结合电位。

  DOI：

  10.1016/j.molstruc.2021.131154

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。
• Synthesis and antioxidant activity study of carbothioamide and their corresponding thiazole derivatives
  作者：Asma、Balakrishna Kalluraya、Nagaraja Manju、Chigahally Lakshmegowda Sharath

  DOI：10.1002/jhet.4018

  日期：2020.8

  A novel series of 5‐(p‐(prop‐2‐ynyloxy)phenyl)‐3‐aryl‐4,5‐dihydropyrazole‐1‐carbothioamides 2a‐f and functionalized 2‐(3‐(aryl)‐5‐(4‐(prop‐2‐ynyloxy)phenyl)‐4,5‐dihydropyrazol‐1‐yl)‐4‐(3‐arylsydnone‐4‐yl)thiazoles 4a‐l were synthesized. The newly synthesized compounds were elucidated by analytical and spectral analysis. From the single‐crystal X‐ray diffraction method, it was observed that 2d crystallizes

  一系列新的5-（对（丙-2-炔氧基）苯基）-3-芳基-4,5-二氢吡唑-1-碳硫酰胺2a-f和官能化的2-（3-（芳基）-5-（4合成了（（丙-2-炔氧基）苯基）-4,5-二氢吡唑-1-基）-4-（3-芳基亚砜基-4-基）噻唑4a-1。通过分析和光谱分析阐明了新合成的化合物。从单晶X射线衍射法可以看出，2d在具有P21 / n空间群的单斜晶体系统中结晶。晶胞参数为a的化合物2d结晶a = 15.0614（19）Å，b = 6.0805（7）Å，c = 20.903（7）Å，α= 114.136（6）o，β= 110.709（14）Ô，γ= 96.553（5）Ô，V = 1790.6（4）3，Z = 4。从Hirshfeld表面计算方法，主要的intercontacts存在于这些分子为H ... H（31.6 ％），C…H（18.2％）和S…H（12.2％）。使用DPPH清除测定法测试了新合成的化合物漂白2
• Design, synthesis, and biological and docking studies of novel epipodophyllotoxin–chalcone hybrids as potential anticancer agents
  作者：Abid Hussain Banday、Vinod V. Kulkarni、Victor J. Hruby

  DOI：10.1039/c4md00325j

  日期：——

  Click-chemistry based design and efficient synthesis of podophyllotoxin–chalcone conjugates as potential topoisomerase-II inhibitors towards the development of better anticancer leads.

  基于点击化学的设计和高效合成卫春素-香豆素共轭物，作为潜在的拓扑异构酶II抑制剂，以开发更好的抗癌药物前导。
• Novel Chalcone‐Phenazine Hybrids Induced Ferroptosis in U87‐MG Cells through Activating Ferritinophagy
  作者：Chunhua Zhang、Qifan Ding、Zhuolu Xia、Hengyu Wang、Feng Jiang、Yuanyuan Lu

  DOI：10.1002/cbdv.202201117

  日期：2023.2

  C4 was verified to induce ferroptosis in U87-MG cells by transcription, lipid peroxidation, lipid ROS assays. Furthermore, C4 was up-regulated LC3-II, degradated FTH1, and then increasing iron resulted in the down-regulation of NCOA4. Together, all above evidences highlighted the potential of compound C4 that triggered ferroptosis by activating ferritinophagy against U87-MG cells.

  本研究设计并合成了37 个以 1,2,3-三唑或乙基为连接基团的新型查耳酮-吩嗪杂化分子（C1∼C13和F1∼F24 ）。一些化合物在体外对U87-MG癌细胞系表现出选择性细胞毒性，其中化合物C4被发现具有最佳的抗增殖活性。SAR 研究表明 1,2,3-三唑基团可能对增强化合物的细胞毒性至关重要。通过转录、脂质过氧化、脂质 ROS 测定，证实C4在 U87-MG 细胞中诱导铁死亡。此外，C4上调 LC3-II，降解 FTH1，然后增加铁导致 NCOA4 下调。总之，上述所有证据都强调了化合物C4通过激活针对 U87-MG 细胞的铁蛋白吞噬来触发铁死亡的潜力。
• 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.