1-(4-氯苯基)-3-(4-氟苯基)-2-丙烯-1-酮 | 98991-31-2

• 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
• 中文名称: 1-(4-氯苯基)-3-(4-氟苯基)-2-丙烯-1-酮
• 英文名称: 1-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
• 英文别名: 1-(4-chloro-phenyl)-3-(4-fluoro-phenyl)-propenone；[2-(4-fluorophenyl)vinyl]-(4-chlorophenyl)-ketone
• CAS: 98991-31-2
• 化学式: C₁₅H₁₀ClFO
• mdl: MFCD00018703
• 分子量: 260.695
• InChiKey: PLCRXLPQUCVAPP-UHFFFAOYSA-N

物化性质

• 沸点：
  385.3±42.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)-3-(4-氟苯基)-2-丙烯-1-酮 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 以63%的产率得到1-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one oxime
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of chalcone oxime derivatives as potential immunosuppressive agents

  摘要：

  A series of deoxybenzoin oximes were recently reported as potent immunosuppressive agents by our group. In order to continue the original research for potential immunosuppressive agents with high efficacy and low toxicity, we synthesized a series of new chalcone oximes and evaluated them for their cytotoxicities and immunosuppressive activities. Among the synthesized compounds, chalcone oximes 25 and 27 exhibited lower cytotoxicities and higher inhibitory activities on anti-CD3/anti-CD28 co-stimulated lymph node cells than other compounds. Specially, compound 27 displayed 200-fold lower cytotoxicity (CC50 = 2174.39 mu M) than cyclosporin A (CC50 = 10.10 mu M) and showed SI value (SI = 176.69) close to cyclosporin A (SI = 154.13). Besides, the preliminary mechanism of inhibition effect of compounds 25 and 27 was also detected by flow cytometry, and the compounds exerted immunosuppressive activities via inducing the apoptosis of activated lymph node cells in a dose dependent manner. Also, the deep mechanism of apoptosis was detected by Western blot analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.080
• 作为产物：
  描述：

  对氟苯甲醛 、 对氯苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以94%的产率得到1-(4-氯苯基)-3-(4-氟苯基)-2-丙烯-1-酮
  参考文献：
  名称：

  草酸区域选择性合成硫代三氮杂-螺衍生物的新方法的发现

  摘要：

  描述了合成一系列新型 thioxotriaza-spiro 衍生物的重要方法。这些新的杂环体系是在 5,6-diamino-2-mercaptopyrimidine-4-ols 存在下通过草酸催化的 α,β-不饱和酮反应获得的；因此，螺环是一步构建的。值得注意的是，这种转化涉及氨基的缩合，然后是烯胺与烯烃的反应，随后由草酸促进的反应得到具有优异区域选择性的螺环化合物。

  DOI：

  10.1055/s-0039-1690204

文献信息

• Novel benzothiazole based sulfonylureas/sulfonylthioureas: design, synthesis and evaluation of their antidiabetic potential
  作者：Chetna Kharbanda、Mohammad Sarwar Alam、Hinna Hamid、Kalim Javed、Sameena Bano、Yakub Ali、Abhijeet Dhulap、Parwez Alam、M. A. Q. Pasha

  DOI：10.1039/c5nj03589a

  日期：——

  Twenty-eight benzothiazole based sulfonylureas/sulfonylthioureas were synthesized and were found to be effective against diabetes as PPAR-γ agonists.

  合成了 28 种基于苯并噻唑的磺酰脲类/磺酰硫脲类，发现它们作为 PPAR-γ 激动剂对糖尿病有效。
• Naphtho[2,3-<i>b</i>]furan-4,9-dione synthesis <i>via</i> palladium-catalyzed reverse hydrogenolysis
  作者：Jimei Li、Jie Zhang、Mingfei Li、Chenyang Zhang、Yongkun Yuan、Renhua Liu

  DOI：10.1039/c8cc09369e

  日期：——

  2-hydroxy-1,4-naphthoquinones with olefins to produce naphtha[2,3-b]furan-4,9-diones and hydrogen (H2). The reaction is catalyzed by commercially available Pd/C without oxidants and hydrogen acceptors, thereby providing an intrinsically waste-free approach for the synthesis of functionalized and potentially biologically relevant naphtha[2,3-b]furan-4,9-diones.

  已经开发了一种反向氢解工艺，用于将2-羟基-1,4-萘醌与烯烃进行两点偶联，以生产石脑油[2,3 - b ]呋喃-4,9-二酮和氢（H 2）。该反应由市售的Pd / C催化，不含氧化剂和氢受体，从而为合成功能化的和潜在生物学相关的石脑油[2,3 - b ]呋喃-4,9-二酮提供了一种本质上无浪费的方法。
• Synthesis and evaluation of pyrazolines bearing benzothiazole as anti-inflammatory agents
  作者：Chetna Kharbanda、Mohammad Sarwar Alam、Hinna Hamid、Kalim Javed、Sameena Bano、Abhijeet Dhulap、Yakub Ali、Syed Nazreen、Saqlain Haider

  DOI：10.1016/j.bmc.2014.09.028

  日期：2014.11

  aims at the synthesis of pyrazolines bearing benzothiazole and their evaluation as anti-inflammatory agents. The synthesized compounds were evaluated for their anti-inflammatory potential using carrageenan induced paw edema model. Two compounds 5a and 5d alleviated inflammation more than the standard drug celecoxib. Eight compounds 5b, 5c, 5e, 5g, 5h, 6b, 6e and 6f showed anti-inflammatory activity comparable

  本研究旨在合成带有苯并噻唑的吡唑啉及其作为抗炎药的评价。使用角叉菜胶诱导的爪水肿模型评价合成的化合物的抗炎潜力。两种化合物5a和5d比标准药物塞来昔布更能减轻炎症。八个化合物5b，5c，5e，5g，5h，6b，6e和6f显示出与塞来昔布相当的抗炎活性。为了理解作用方式，进行了COX-2酶测定和TNF-α测定。评估所有活性化合物的细胞毒性。对未发现有细胞毒性的活性化合物进行了致溃疡风险评估。在十种活性化合物中，最终发现两种化合物（5d和6f）是最有效的抗炎药，可抑制COX-2酶活性和TNF-α的产生，而不会产生细胞毒性或致溃疡性。
• Synthesis and Evaluation of Human Monoamine Oxidase Inhibitory Activities of Some 3,5-Diaryl-N-substituted-4,5-dihydro-1H-pyrazole-1-carbothioamide Derivatives
  作者：Kerem Şentürk、Oya Unsal Tan、Samiye Yabanoğlu Çiftçi、Gülberk Uçar、Erhan Palaska

  DOI：10.1002/ardp.201100448

  日期：2012.9

  Sixteen 3‐aryl‐5‐(4‐fluorophenyl)‐N‐substituted‐4,5‐dihydro‐1H‐pyrazole‐1‐carbothioamide derivatives were synthesized and their structure were identified by UV, IR, 1H NMR, mass spectra, and microanalyses. The compounds were evaluated in vitro for their human monoamine oxidase (hMAO) inhibitory activities and their MAO‐A and ‐B selectivity. All the compounds were found to potently inhibit MAO‐A isoforms

  合成了 16 种 3-芳基-5-(4-氟苯基)-N-取代的-4,5-二氢-1H-吡唑-1-碳硫酰胺衍生物，并通过紫外、红外、1H 核磁共振、质谱和质谱鉴定了它们的结构。微量分析。体外评估了这些化合物的人单胺氧化酶 (hMAO) 抑制活性及其 MAO-A 和 MAO-B 选择性。发现所有化合物均能有效抑制 MAO-A 异构体。发现 5-(4-氟苯基)-3-(4-甲氧基苯基)-N-甲基-4,5-二氢-1H-吡唑-1-碳硫酰胺 (1.0 × 10-3 µM) 最有选择性地抑制 hMAO-A并且有力地。还使用对接研究预测了 5-(4-氟苯基)-3-(4-甲氧基苯基)-N-甲基-4,5-二氢-1H-吡唑-1-碳硫酰胺与 hMAO-A 的结合模式。
• Synthesis and cytotoxic activities of some pyrazoline derivatives bearing phenyl pyridazine core as new apoptosis inducers
  作者：Riham F. George、Marwa A. Fouad、Iman E.O. Gomaa

  DOI：10.1016/j.ejmech.2016.01.048

  日期：2016.4

  to the formation of new pyrazoline derivatives 8a-8u. All final compounds were characterized by spectral and elemental analyses. They were screened for their antiproliferative activities against A549 (lung), HepG-2 (liver), CaCo-2 (intestinal) and MCF-7 (breast) cancer cell lines. Some of the synthesized compounds exhibited promising antiproliferative activities especially compound 8k with IC50 values

  在碱性条件下，将查尔酮3a - 3u与3-肼基-6-苯基哒嗪7环合导致形成新的吡唑啉衍生物8a-8u。所有最终化合物均通过光谱和元素分析进行​​表征。筛选了它们对A549（肺），HepG-2（肝），CaCo-2（肠）和MCF-7（乳腺癌）癌细胞系的抗增殖活性。某些合成的化合物显示出有希望的抗增殖活性，尤其是具有IC 50的化合物8k分别针对HepG-2，MCF-7和CaCo-2癌细胞系的8.33、1.67和10μM的最高值。此外，它们的抗增殖活性是由于细胞凋亡而不是坏死诱导，除了化合物8h表现出相同的凋亡和坏死特性。化合物8k显示caspase-3活性增加了5倍，表明细胞凋亡通过caspase-3活化而进行。