1-(pyridin-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 374913-12-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(pyridin-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: PTPO；1-pyridin-2-yl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 374913-12-9
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: BPHYOXFAYJPCCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(pyridin-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 、 氨基硫脲 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 以65%的产率得到1-thiocarbamoyl-3-pyridyl-5-(3,4,5-trimethoxyphenyl)-2-pyrazoline
  参考文献：
  名称：

  Spectral studies of 2-pyrazoline derivatives: Structural elucidation through single crystal XRD and DFT calculations

  摘要：

  A series of biologically active N-thiocarbamoyl pyrazoline derivatives have been synthesized using anhydrous potassium carbonate as the catalyst. All the synthesized compounds were characterized by FT-IR, H-1 NMR, C-13 NMR spectral studies, LCMS, CHN Analysis and X-ray diffraction analysis (compound 7). In order to supplement the XRD parameters, molecular modelling was carried out by Gaussian 03W. From the optimized structure, the energy, dipolemoment and HOMO-LUMO energies of all the systems were calculated. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2013.12.032
• 作为产物：
  描述：

  2-乙酰基吡啶 、 3,4,5-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以74.7%的产率得到1-(pyridin-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  查耳酮衍生物作为抗阿尔茨海默病的多功能药物的设计、合成和评估

  摘要：

  合成了15 种查耳酮衍生物3a – 3o，并作为抗阿尔茨海默病的多功能药物进行了评估。体外研究表明，这些化合物在 20 μM 时有效抑制自诱导 Aβ 1-42聚集的范围为 45.9–94.5 %，并充当潜在的抗氧化剂。总结了它们的构效关系。特别是，( 2E )-3-[4-(二甲基氨基)苯基]-1-(吡啶-2-基)丙-2-烯-1-酮( 3g )在20℃时表现出94.5%的优异抑制活性μM，在20 μM浓度下可分解自诱导的Aβ 1-42聚集原纤维，比例为57.1 %。另外，复方3g对Cu 2+表现出良好的螯合能力，能有效抑制和解聚Cu 2+诱导的Aβ聚集。此外，化合物3g具有低细胞毒性，显着逆转 Aβ 1-42诱导的 SH-SY5Y 细胞损伤。更重要的是，化合物3g显着改善了东莨菪碱引起的小鼠记忆障碍。总之，所有结果表明化合物3g是一种潜在的 AD 治疗多功能药物。

  DOI：

  10.1002/cbdv.202100341

文献信息

• Synthesis and Anticancer Activity of 3-(Substituted Aroyl)-4-(3,4,5-trimethoxyphenyl)-1<i>H</i>-pyrrole Derivatives
  作者：Xiao-Ping Zhan、Lan Lan、Shuai Wang、Kai Zhao、Yu-Xuan Xin、Qi Qi、Yao-Lin Wang、Zhen-Min Mao

  DOI：10.1002/cbdv.201600219

  日期：2017.2

  A series of 3-(substituted aroyl)-4-(3,4,5-trimethoxyphenyl)-1H-pyrrole derivatives were synthesized and determined for their anticancer activity against eleven cancer cell lines and two normal tissue cell lines using MTT assay. Among the synthesized compounds, compound 3f was the most potent compound against A375, CT-26, HeLa, MGC80-3, NCI-H460 and SGC-7901 cells (IC50 = 8.2 - 31.7 μm); 3g, 3n and

  合成了一系列3-（取代的芳酰基）-4-（3,4,5-三甲氧基苯基）-1H-吡咯衍生物，并使用MTT法测定了它们对十一种癌细胞系和两种正常组织细胞系的抗癌活性。在合成的化合物中，化合物3f是针对A375，CT-26，HeLa，MGC80-3，NCI-H460和SGC-7901细胞的最有效化合物（IC50 = 8.2-31.7μm）；3g，3n和3a分别是对抗CHO（IC50 = 8.2μm），HCT-15（IC50 = 21μm）和MCF-7细胞（IC50 = 18.7μm）最有效的化合物。重要的是，所有目标化合物都没有表现出对正常组织细胞的细胞毒性（IC50> 100μm）。因此，这些具有有效的抗癌活性和低毒性的化合物具有开发新的抗癌化学治疗剂的潜力。
• Design, Synthesis, and Evaluation of Chalcone Derivatives as Multifunctional Agents against Alzheimer's Disease
  作者：Xiao‐Qin Wang、Lu‐Yi Zhou、Ren‐Xian Tan、Guo‐Peng Liang、Si‐Xian Fang、Wei Li、Mei Xie、Yu‐Hao Wen、Jia‐Qiang Wu、Yi‐Ping Chen

  DOI：10.1002/cbdv.202100341

  日期：2021.11

  Fifteen chalcone derivatives 3a–3o were synthesized, and evaluated as multifunctional agents against Alzheimer's disease. In vitro studies revealed that these compounds inhibited self-induced Aβ1-42 aggregation effectively ranged from 45.9–94.5 % at 20 μM, and acted as potential antioxidants. Their structure-activity relationships were summarized. In particular, (2E)-3-[4-(dimethylamino)phenyl]-1-

  合成了15 种查耳酮衍生物3a – 3o，并作为抗阿尔茨海默病的多功能药物进行了评估。体外研究表明，这些化合物在 20 μM 时有效抑制自诱导 Aβ 1-42聚集的范围为 45.9–94.5 %，并充当潜在的抗氧化剂。总结了它们的构效关系。特别是，( 2E )-3-[4-(二甲基氨基)苯基]-1-(吡啶-2-基)丙-2-烯-1-酮( 3g )在20℃时表现出94.5%的优异抑制活性μM，在20 μM浓度下可分解自诱导的Aβ 1-42聚集原纤维，比例为57.1 %。另外，复方3g对Cu 2+表现出良好的螯合能力，能有效抑制和解聚Cu 2+诱导的Aβ聚集。此外，化合物3g具有低细胞毒性，显着逆转 Aβ 1-42诱导的 SH-SY5Y 细胞损伤。更重要的是，化合物3g显着改善了东莨菪碱引起的小鼠记忆障碍。总之，所有结果表明化合物3g是一种潜在的 AD 治疗多功能药物。
• Combining phosphonic acid-functionalized anchoring ligands with asymmetric ancillary ligands in bis(diimine)copper(<scp>i</scp>) dyes for dye-sensitized solar cells
  作者：Annika Büttner、Sven Y. Brauchli、Raphael Vogt、Edwin C. Constable、Catherine E. Housecroft

  DOI：10.1039/c5ra25447g

  日期：——

  A 6,6′-dimethyl substitution pattern in L_anchor in [Cu(L_anchor)(L_ancillary)]⁺ dyes in DSCs is superior to two phenyl groups, even when steric crowding is alleviated by using asymmetric L_ancillary.

  在DSCs中，[Cu(L_anchor)(L_ancillary)]⁺染料中L_anchor中的6,6'-二甲基取代模式优于两个苯基，即使使用不对称的L_ancillary缓解立体阻碍也是如此。
• Synthesis of Nitrogen Containing Chalcone: A Highly Sensitive and Selective Fluorescent Chemosensor for the Fe3+ Metal Ion in Aqueous Media
  作者：Abdullah M. Asiri、Mona Mohammad Al-Amari、Salman A. Khan

  DOI：10.1007/s10895-020-02534-x

  日期：2020.7

  benzaldehyde. The structure of the compound has been confirmed by spectroscopic techniques. Interaction of chalcone with different metal cations was analyzed based on the fluorescence behavior. Results show that chalcone act as on-off switching fluorescent chemosensor for selective and sensitive detection iron metal ion. Mechanism of quenching and complexation were resolute by Benesi-Hildebrand, Stern-Volmer

  通过2-乙酰基吡啶与3,4,5-三甲氧基苯甲醛的反应合成标题化合物（PTPO）。该化合物的结构已通过光谱技术证实。基于荧光行为分析了查尔酮与不同金属阳离子的相互作用。结果表明，查耳酮可作为选择性开关和灵敏检测铁金属离子的开关化学荧光传感器。Benesi-Hildebrand，Stern-Volmer图和Job-plot确定了淬灭和络合的机理。
• Spectral studies of 2-pyrazoline derivatives: Structural elucidation through single crystal XRD and DFT calculations
  作者：D. Chinnaraja、R. Rajalakshmi、T. Srinivasan、D. Velmurugan、J. Jayabharathi

  DOI：10.1016/j.saa.2013.12.032

  日期：2014.4

  A series of biologically active N-thiocarbamoyl pyrazoline derivatives have been synthesized using anhydrous potassium carbonate as the catalyst. All the synthesized compounds were characterized by FT-IR, H-1 NMR, C-13 NMR spectral studies, LCMS, CHN Analysis and X-ray diffraction analysis (compound 7). In order to supplement the XRD parameters, molecular modelling was carried out by Gaussian 03W. From the optimized structure, the energy, dipolemoment and HOMO-LUMO energies of all the systems were calculated. (C) 2013 Elsevier B.V. All rights reserved.