1-(4-hydroxyphenyl)-3-(o-tolyl)propenone | 173928-78-4

• 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-hydroxyphenyl)-3-(o-tolyl)propenone
• 英文别名: 4′-hydroxy-2-methylchalcone；4'-hydroxy-2-methylchalcone；2-Methyl-4'-hydroxychalcone；1-(4-hydroxyphenyl)-3-(2-methylphenyl)prop-2-en-1-one
• CAS: 173928-78-4
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: CFCIAXFIRGJVBG-UHFFFAOYSA-N

物化性质

• 沸点：
  426.2±45.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxyphenyl)-3-(o-tolyl)propenone 在 六氯环三磷腈 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以76%的产率得到C₉₆H₇₈N₃O₁₂P₃
  参考文献：
  名称：

  Synthesis, characterization and dielectric properties of phosphazenes containing chalcones

  摘要：

  The new hexasubstitue-cyclophosphazene compounds containing chalcone derivatives (2-11) were obtained from the reactions of hexachlorocyclotriphosphazene (1) with several hydroxy chalcones in K2CO3/acetone system. All products were generally obtained in high yields. The structures of the compounds were defined by elemental analysis, FT-IR,H-1,C-13 and P-31 NMR spectroscopy. Dielectric measurements for phosphazenes containing chalcone compounds (5-8) were carried out by means of an impedance analyzer as a function of temperature and frequency. Dielectric properties of samples prepared in a plate form were measured at room temperature over the frequency range 50 Hz to 2 kHz and given as compared with each other. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.04.070
• 作为产物：
  描述：

  1-[4-[(四氢-2H-吡喃-2-基)氧基]苯基]乙酮 在 盐酸 、 barium hydroxide octahydrate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 1-(4-hydroxyphenyl)-3-(o-tolyl)propenone
  参考文献：
  名称：

  设计，合成和体外对某些1-甲基-3,5-二苯基-4,5-二氢-1 H-吡唑类化合物的hMAO-B抑制性评估

  摘要：

  设计，合成了一系列1-甲基-3,5-二苯基-4,5-二氢-1 H-吡唑类化合物（3a - k和4a - u），并评估了它们对两种hMAO同工型的抑制作用。发现大多数衍生物是有效的和选择性的hMAO-B抑制剂。尤其是，衍生物3g与选择性抑制剂司来吉兰相比具有更高的hMAO-B亲和力，并具有高选择性指数（SI = 145）。最具选择性的hMAO-B抑制剂是3-甲基类似物3f，SI高于909。

  DOI：

  10.1016/j.bmcl.2013.07.035

文献信息

• Analysis of Intermolecular Interactions in 2,3,5 Trisubstituted Pyrazoles Derivatives: Insights into Crystal Structures, Gaussian B3LYP/6-311G (d,p), PIXELC and Hirshfeld Surface
  作者：Gayathri Purushothaman、Vijay Thiruvenkatam

  DOI：10.1007/s10870-016-0667-6

  日期：2016.9

  Two derivatives of pyrazole have been synthesized with one of the systematic substitutions made on the ortho position of the phenyl ring attached to the pyrazole moiety and characterised via single crystal X-ray diffraction. The nature of the molecules appear as planar with the hydrogen bonding features analysed quantitatively. The derivatives are geometrically optimized and studied for its molecular confirmation at the B3LYP/6-311G (d,p). The structure overlay, molecular packing and intermolecular hydrogen bonding are studied quantitatively using Hirshfeld surface and 2D fingerprint plots. In both the compounds, packing of the molecules is derived via strong O–H···N and weak C–H···O, C–H···π interactions stabilizing the packing. Further, the structure overlay between the experimental structures and the geometrically optimized structures along with frequency analysis at the quantum chemical level shows the deviation in the central pyrazole moiety and the substituted phenyl ring with the RMSD value of 0.5051 and 0.6305 Å respectively. The lattice energy is calculated for both the compounds using PIXELC module in Coulomb–London–Pauli (CLP) package and is partitioned into corresponding coulombic, polarization, dispersion and repulsion contributions.

  我们合成了吡唑的两种衍生物，其中一种在吡唑分子上连接的苯基环的正交位置进行了系统取代，并通过单晶 X 射线衍射进行了表征。分子的性质显示为平面，并对氢键特征进行了定量分析。这些衍生物在 B3LYP/6-311G (d,p) 下进行了几何优化和分子确认研究。利用 Hirshfeld 表面和二维指纹图定量研究了结构叠加、分子堆积和分子间氢键。在这两种化合物中，分子的堆积是通过强的 O-H--N和弱的 C-H--O、C-H--π 相互作用来稳定堆积的。此外，实验结构与几何优化结构之间的结构叠加以及量子化学水平的频率分析表明，中央吡唑分子和取代的苯基环存在偏差，其 RMSD 值分别为 0.5051 和 0.6305 Å。使用库仑-伦敦-保利（CLP）软件包中的 PIXELC 模块计算了这两种化合物的晶格能，并将其划分为相应的库仑贡献、极化贡献、色散贡献和排斥贡献。
• Synthesis, structural and thermal characterizations, dielectric properties and in vitro cytotoxic activities of new 2,2,4,4-tetra(4′-oxy-substituted-chalcone)-6,6-diphenylcyclotriphosphazene derivatives
  作者：Kenan Koran、Çiğdem Tekin、Fatih Biryan、Suat Tekin、Süleyman Sandal、Ahmet Orhan Görgülü

  DOI：10.1007/s00044-017-1810-4

  日期：2017.5

  In this study, we aimed to investigate the relationship between the cytotoxic and dielectric properties of newly synthesized 2,2,4,4-tetra(4′-oxy-substituted-chalcone)-6,6-diphenylcyclotriphosphazene derivatives (3–10). Firstly, 2,2,4,4-tetrachloro-6,6-diphenyl cyclotriphosphazene (2) was obtained through Friedel Crafts alkylation in the presence of hexachlorocyclotriphosphazene, benzene and triethylamine

  在这项研究中，我们旨在研究新合成的2,2,4,4-四（4'-氧基取代的查尔酮）-6,6-二苯基环三磷腈衍生物的细胞毒性与介电性能之间的关系（3-10）。首先，在六氯环三磷腈，苯和三乙胺，无水AlCl 3存在下，通过Friedel Crafts烷基化反应得到2,2,4,4-四氯-6,6-二苯基环三磷腈（2）。化合物3–10是在K 2 CO 3存在下由羟基查耳酮化合物（1a–h）与2的反应合成的并首次在丙酮溶剂中，通过阻抗分析仪检查了化合物3-10的介电常数，介电损耗因子和交流电导率随频率的变化。通过比色MTT测定法分析了5种不同浓度（1、5、25、50和100 µM）中化合物3-10的体外细胞毒性活性，该测定基于活细胞的线粒体对人卵巢的MTT盐还原作用癌细胞（A2780）和人前列腺癌（PC-3和LNCaP）细胞系。通过使用计算机上的Graphpad棱镜6程序计算出LogIC 50值为3-10
• 含查尔酮的芳氧羧酸酯类化合物的合成方法及其在农药上的应用
  申请人：江苏大学

  公开号：CN110041198B

  公开（公告）日：2022-03-22

  本发明属于除草剂技术领域，具体提供了一种含查尔酮的芳氧羧酸酯类化合物的合成方法及其在农药上的应用，合成步骤如下：适当温度下，按比例将4‑羟基查尔酮衍生物与芳氧乙酰氯加入到适当反应溶剂中，加入适当催化剂，进行反应，反应完成后，除去溶剂，向残余物中加入NaOH溶液，过滤、洗涤、干燥，重结晶即得含查尔酮的芳氧羧酸酯类化合物。本发明提供了一种简单、有效的方法合成含查尔酮的芳氧羧酸酯类化合物，且本发明的化合物具有较强的除草活性。
• Design, synthesis, anti-acetylcholinesterase evaluation and molecular modelling studies of novel coumarin-chalcone hybrids
  作者：Aso Hameed Hasan、Sonam Shakya、Faiq H.S. Hussain、Sankaranarayanan Murugesan、Subhash Chander、Mohammad Rizki Fadhil Pratama、Shajarahtunnur Jamil、Basundhara Das、Subhrajit Biswas、Joazaizulfazli Jamalis

  DOI：10.1080/07391102.2022.2162583

  日期：——

  value ranging from 0.201 ± 0.008 to 1.047 ± 0.043 μM. Hybrid 8d having chloro substitution on ring-B of the chalcone scaffold showed relatively better potency, with IC50 value of 0.201 ± 0.008 μM compared to other members of the series. The reference drug, galantamine, exhibited an IC50 at 1.142 ± 0.027 μM. Computational studies revealed that designed compounds bind to the peripheral anionic site (PAS)

   抽象的 负责神经递质乙酰胆碱 (ACh) 水解分解的主要酶是乙酰胆碱酯酶 (AChE)。乙酰胆碱酯酶抑制剂 (AChEI) 是治疗阿尔茨海默病 (AD) 和痴呆症最常用的一类药物。现有疗法的局限性，如副作用、药物耐受性和阻止疾病进展无效等，推动了对更好、更有效和更安全药物的需求。在本研究中，通过 FT-IR、NMR 和 HR-MS 等光谱技术设计、合成并表征了一系列 14 种新型查耳酮-香豆素衍生物 ( 8a-n )。随后，通过Ellman方法测试了合成的化合物抑制乙酰胆碱酯酶（AChE）活性的能力。所有测试的化合物均显示出 AChE 抑制作用，IC 50值范围为 0.201 ± 0.008 至 1.047 ± 0.043 μM。查耳酮支架的 B 环上有氯取代的杂化物8d显示出相对更好的效力，与该系列的其他成员相比，IC 50值为 0.201 ± 0.008 μM。参考药物加兰他敏的 IC
• Synthesis and antimalarial evaluation of 1, 3, 5-trisubstituted pyrazolines
  作者：Badri Narayan Acharya、Deepika Saraswat、Mugdha Tiwari、Asish Kumar Shrivastava、Ramarao Ghorpade、Saroj Bapna、Mahabir Parshad Kaushik

  DOI：10.1016/j.ejmech.2009.10.023

  日期：2010.2

  A series of 1,3,5-trisubstituted pyrazolines were synthesized and evaluated for in vitro antimalarial efficacy against chloroquine sensitive (MRC-02) as well as chloroquine resistant (RKL9) strains of Plasmodium falciparum. The activity was at nano molar concentration. beta-hematin formation inhibition activity (BHIA(50)) of the pyrazolines were determined and correlated with antimalarial activity. A reasonably good correlation (r = 0.62) was observed between antimalarial activity (IC50) and BHIA(50). This suggests that antimalarial mode of action of this class of compounds appears to be similar to that of chloroquine and involves the inhibition of hemozoin formation. Some of the compounds were showing better antimalarial activity than chloroquine against resistant strain of P. falciparum and were also found active in the in vivo experiment. (C) 2009 Elsevier Masson SAS. All rights reserved.