1-(2-hydroxyphenyl)-3-(3-(trifluoromethyl)phenyl)prop-2-en-1-one | 73110-80-2

• 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-(2-hydroxyphenyl)-3-(3-(trifluoromethyl)phenyl)prop-2-en-1-one
• 英文别名: 1-(2-hydroxyphenyl)-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one
• CAS: 73110-80-2
• 化学式: C₁₆H₁₁F₃O₂
• 分子量: 292.257
• InChiKey: ICDJAWVPKJVBFG-UHFFFAOYSA-N

物化性质

• 沸点：
  401.5±45.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 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：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)-3-(3-(trifluoromethyl)phenyl)prop-2-en-1-one 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以63%的产率得到3-hydroxy-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one
  参考文献：
  名称：

  钌（II）催化的脱羰环化反应合成螺并苯并呋喃酮

  摘要：

  据报道，炔烃通过六元化合物的C / H / C-C活化而首次脱羰基插入。在配体PPh 3存在下，Ru-催化的3-羟基-2-苯基色酮与炔烃的反应最有效，可提供螺茚二苯并呋喃酮。与以前报道的金属催化的脱羰环化反应不同，在本脱羰环化反应中，环化发生在一氧化碳挤出之前。

  DOI：

  10.1002/anie.201710049
• 作为产物：
  描述：

  3-三氟甲基苯甲醛 、 2'-羟基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 1-(2-hydroxyphenyl)-3-(3-(trifluoromethyl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  钌（II）催化的脱羰环化反应合成螺并苯并呋喃酮

  摘要：

  据报道，炔烃通过六元化合物的C / H / C-C活化而首次脱羰基插入。在配体PPh 3存在下，Ru-催化的3-羟基-2-苯基色酮与炔烃的反应最有效，可提供螺茚二苯并呋喃酮。与以前报道的金属催化的脱羰环化反应不同，在本脱羰环化反应中，环化发生在一氧化碳挤出之前。

  DOI：

  10.1002/anie.201710049

文献信息

• Synthesis of 3-HCF₂S-Chromones through Tandem Oxa-Michael Addition and Oxidative Difluoromethylthiolation
  作者：Pingshun Zhang、Wanzhi Chen、Miaochang Liu、Huayue Wu

  DOI：10.1021/acs.orglett.9b03396

  日期：2019.12.6

  A simple protocol for the synthesis of difluoromethylthiolated chromen-4-ones using elemental sulfur and ClCF2CO2Na as the difluoromethylthiolating agent is described. Three-component reactions of 2'-hydroxychalcones, ClCF2CO2Na, and sulfur under basic conditions using TEMPO as the oxidant afforded HCF2S-containing 4H-chromen-4-one and 9H-thieno[3,2-b]chromen-9-one derivatives in good yield. The protocol

  描述了一种使用元素硫和ClCF2CO2Na作为二氟甲基硫醇化试剂合成二氟甲基硫醇化chromen-4-ones的简单方案。在碱性条件下，使用TEMPO作为氧化剂，在2'-羟基查耳酮，ClCF2CO2Na和硫的三组分反应下，可得到含HCF2S的4H-色烯-4-酮和9H-硫代[3,2-b]铬-9-酮衍生物产量高。该方案是实用且有效的，并且起始材料便宜且容易获得。
• Enantioselective Synthesis of 2-Substituted-1,5-Benzodiazepines through Domino Reaction of o-Phenylenediamine and Chalcone Derivatives
  作者：Xuan Fu、Juhua Feng、Zhenhua Dong、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/ejoc.201100938

  日期：2011.9

  Chiral 2-substituted-1,5-benzodiazepine derivatives were synthesized for the first time from an enantioselective domino reaction involving o-phenylenediamine and 2′-hydroxychalcones. The titanium complex formed from chiral ligand 1a derived from (S)-BINOL and L-prolineamide promoted the reaction and gave the products in good yields with up to 82 % ee.

  手性 2-取代-1,5-苯二氮卓衍生物首次从涉及邻苯二胺和 2'-羟基查耳酮的对映选择性多米诺反应合成。由衍生自 (S)-BINOL 和 L-脯氨酸酰胺的手性配体 1a 形成的钛配合物促进了反应，并以高达 82% ee 的良好收率得到了产物。
• Inhibition of LPS-stimulated ROS production by fluorinated and hydroxylated chalcones in RAW 264.7 macrophages with structure-activity relationship study
  作者：Ganesh Bist、Nirmala Tilija Pun、Til Bahadur Thapa Magar、Aarajana Shrestha、Hye Jin Oh、Amrita Khakurel、Pil-Hoon Park、Eung-Seok Lee

  DOI：10.1016/j.bmcl.2017.01.061

  日期：2017.3

  previous fluorinated and/or hydroxylated chalcones studies, thirty-six compounds were designed as phenyl or hydroxyphenyl bearing fluoro, trifluoromethyl or trifluoromethoxy phenyl propenones and synthesized by applying modified Claisen-Schmidt condensation reaction as a single step. Inhibitory effects of the synthesized compounds on ROS production stimulated by LPS in RAW 264.7 macrophage were evaluated

  基于先前的氟化和/或羟基化查耳酮研究的重要性，将三十六种化合物设计为带有氟，三氟甲基或三氟甲氧基苯基丙烯酮的苯基或羟基苯基，并通过一步法应用修饰的Claisen-Schmidt缩合反应进行合成。评估了合成的化合物对RAW 264.7巨噬细胞中LPS刺激的ROS产生的抑制作用。结构-活性关系（SAR）研究表明，具有对-羟基苯基与间-氟或间-三氟甲基苯基结合，以及间/对-羟基苯基与邻位结合的化合物-三氟甲氧基苯基在抑制RAW 264.7巨噬细胞中LPS刺激的ROS产生中起重要作用。在具有对-羟基苯基基团和邻-三氟甲氧基苯基基团的化合物30中观察到对RAW 264.7巨噬细胞中LPS刺激的ROS产生的最显着的抑制作用。
• Topoisomerase IIα inhibitory and antiproliferative activity of dihydroxylated 2,6-diphenyl-4-fluorophenylpyridines: Design, synthesis, and structure-activity relationships
  作者：Surendra Kunwar、Soo-Yeon Hwang、Pramila Katila、Tara Man Kadayat、Ah-Reum Jung、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.bmcl.2022.128606

  日期：2022.3

  biological results, the structure-activity relationships of the synthesized derivatives emphasized the significance of 4-trifluoromethoxyphenyl groups for strong antiproliferative activity and 4-fluorophenyl groups for strong topo IIα inhibition. Furthermore, meta- and para-phenolic groups at the 2- and 4-positions are favorable for strong topo IIα inhibitory and antiproliferative activity. The research findings

  合成了包含氟苯基、三氟甲基苯基和三氟甲氧基苯基的 54 个新系列 2-苯酚-4-芳基-6-羟基苯基吡啶，并测试了对不同癌细胞系的拓扑异构酶 IIα 抑制和抗增殖活性，以试图研究拓扑异构酶以 IIα 为靶点的前瞻性抗癌药物，以应对现有治疗方案的局限性。与阳性对照相比，几种化合物11-12、37、50和51显示出高抗增殖活性，而几种4-氟苯基取代的化合物13-14和18显示出强烈的拓扑异构酶 IIα 抑制作用。令人惊讶的是，大多数化合物对 HCT15 结直肠腺癌和 T47D 乳腺癌细胞系具有显着的抗增殖作用。此外， 4位对氟苯基和2位和6位间酚基团的化合物12抑制增殖的HeLa宫颈腺癌细胞，IC 50值为1.28 μM。基于生物学结果，合成衍生物的构效关系强调了 4-三氟甲氧基苯基对于强抗增殖活性和 4-氟苯基对于强拓扑 IIα 抑制的重要性。此外，meta - 和para2 位和 4 位的 -
• Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies
  作者：Jamshaid Ashraf、Ehsan Ullah Mughal、Amina Sadiq、Maryam Bibi、Nafeesa Naeem、Anser Ali、Anam Massadaq、Nighat Fatima、Asif Javid、Muhammad Naveed Zafar、Bilal Ahmad Khan、Muhammad Faizan Nazar、Amara Mumtaz、Muhammad Nawaz Tahir、Masoud Mirzaei

  DOI：10.1080/07391102.2020.1805364

  日期：2021.12.12

  To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened forin vitroagainst mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis,H-1-,C-13-NMR) and mass spectrometry (EI-MS). The structure of compound15was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibioticsi.e.Cefixime and Clotrimazole. Amongst the series, the compounds2, 4, 5, 6, 7, 10, 11, 14and22exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound2(IC50= 0.280 +/- 0.010 mu g/ml) was found almost sixfold and derivative5(IC50= 0.230 +/- 0.020 mu g/ml) about sevenfold more active as compared to standard Kojic acid (IC50=1.79 +/- 0.6 mu g/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma