(4-hydroxy-3-methylphenyl)(4-fluorophenyl)methanone | 360765-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-hydroxy-3-methylphenyl)(4-fluorophenyl)methanone
• 英文别名: 4'-fluoro-3-methyl-4-hydroxybenzophenone；(4-Hydroxy-3-methylphenyl)(4-fluorophenyl)methanone；(4-fluorophenyl)-(4-hydroxy-3-methylphenyl)methanone
• CAS: 360765-71-5
• 化学式: C₁₄H₁₁FO₂
• 分子量: 230.239
• InChiKey: WEGQVSVDCGRNRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C(Solv: ethanol (64-17-5))
• 沸点：
  394.7±42.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-hydroxy-3-methylphenyl)(4-fluorophenyl)methanone 在 2,6-二甲基吡啶 、 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 14.5h， 生成 2-oxo-2H-chromene-3-carboxylic acid N'-{2-[4-(4-fluorobenzoyl)-2-methylphenoxy]acetyl}hydrazide
  参考文献：
  名称：

  新型二苯甲酮偶联香豆素类似物的设计、合成和抗癌特性

  摘要：

  在当前情况下，开发具有特定靶点的抗癌药物在现代化学生物学中至关重要。观察到二苯甲酮和香豆素核的重要性，设计和合成带有香豆素核的新型二苯甲酮衍生物 (8a-o) 是值得的。此外，还筛选了它们在体外针对密歇根癌症基金会-7 (MCF-7) 和埃利希腹水瘤 (EAT) 细胞系及其生物标志物的前瞻性抗癌活性，然后进行了有关磷酸肌醇 3-激酶 (PI3K) 和caspase 通过分子对接。据报道，二苯甲酮是靶向肿瘤血管生成的潜在药物。因此，在存在化合物 8a-o 的情况下，观察到血管生成依赖的 CAM 等体内模型系统中新血管的形成。

  DOI：

  10.1002/ardp.201300298
• 作为产物：
  描述：

  对氟苯甲酰氯 在 aluminum (III) chloride 、 sodium hydroxide 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 生成 (4-hydroxy-3-methylphenyl)(4-fluorophenyl)methanone
  参考文献：
  名称：

  新型二苯甲酮偶联香豆素类似物的设计、合成和抗癌特性

  摘要：

  在当前情况下，开发具有特定靶点的抗癌药物在现代化学生物学中至关重要。观察到二苯甲酮和香豆素核的重要性，设计和合成带有香豆素核的新型二苯甲酮衍生物 (8a-o) 是值得的。此外，还筛选了它们在体外针对密歇根癌症基金会-7 (MCF-7) 和埃利希腹水瘤 (EAT) 细胞系及其生物标志物的前瞻性抗癌活性，然后进行了有关磷酸肌醇 3-激酶 (PI3K) 和caspase 通过分子对接。据报道，二苯甲酮是靶向肿瘤血管生成的潜在药物。因此，在存在化合物 8a-o 的情况下，观察到血管生成依赖的 CAM 等体内模型系统中新血管的形成。

  DOI：

  10.1002/ardp.201300298

文献信息

• Prototropic processes in benzaurins. 19F and 1H NMR spectra of fluoro- and methylsubstituted 4-hydroxyphenyl-diphenylcarbinols, related fuchsones and benzaurins
  作者：Poul Hansen、Alexsander Peregudov、Dimitrii Kravtsov、Antonina Krylova、Galina Babakhina、Ludmila Golovchenko、Valentina Pachevskaya

  DOI：10.2478/s11532-011-0003-0

  日期：2011.4.1

  1H and 19F chemical shifts have been determined for a number of substituted 4-hydroxyphenyl-diphenyl carbinols containing fluorine in a 3-, 3*- or 4*-position, and for similar compounds containing additional methyl groups in a position of 3, 3** or 4**. The same data have been obtained for the fuchsones prepared by dehydration of the above carbinols. On this basis chemical shifts of fluorine in different

  研究了苯甲脲类的互变异构和水合。对于许多在3-，3 *-或4 *-位含氟的取代的4-羟基苯基-二苯基甲醇和在3位上含其他甲基的类似化合物，已确定1 H和19 F的化学位移，3 **或4 **。通过上述甲醇的脱水制备的紫红色已经获得了相同的数据。在此基础上，已经评估了氟在不同位置的化学位移，作为监测4-羟苯基向半醌部分转化的监测器。在19F NMR可用于监测4 **-氟苯并尿素和相关的3,3 *-二取代和3,3 *，5,5 *-四甲基取代的化合物由于添加了水分子和来研究后两个苯甲酰脲和3,3 *，4 **三氟苯甲酰脲的互变异构现象。此外，氟和甲基的化学位移对取代的品红中的 顺反 异构体敏感 。
• Synthesis, analgesic, anti-inflammatory, ulcerogenic evaluation, and docking study of (benzoylphenoxy)-N-{5-[2-methylphenyl-6-chlorobenzoxazole]} acetamides as COX/5-LOX inhibitor
  作者：M.J. Nagesh Khadri、Hussien Ahmed Khamees、Salma Kouser、Zabiulla、Shaukath Ara Khanum

  DOI：10.1016/j.molstruc.2022.134240

  日期：2023.1

  5-LOX inhibitors with analgesic and anti-inflammatory effectiveness and very less gastrointestinal toxicity have been recognized as constructive and sustainable agents for inflammatory treatment. In this approach, a series of titled compounds (10a-j) were developed, synthesized, and evaluated in terms of in-vitro COX and LOX enzyme inhibition followed by analgesic, anti-inflammatory, and the ulcerogenic

  COX 和 5-LOX 抑制剂具有镇痛和抗炎效果以及极低的胃肠道毒性，已被公认为炎症治疗的建设性和可持续药物。在这种方法中，开发、合成了一系列标题化合物 ( 10a-j )，并在体外COX 和 LOX 酶抑制以及镇痛、抗炎和致溃疡活性方面进行了评估。对表现出潜在镇痛活性的化合物10a-c、10e和10g-10i进行了抗炎评估，随后验证了强效抗炎化合物的致溃疡作用。化合物10b苯环上的甲基邻位取代和氯基对位取代，苯并恶唑上的二苯甲酮苯甲酰基环上氯基的间位取代，观察到具有良好的抑制效力。此外，使用 Autodock 工具对接软件进行计算机研究。
• Synthesis and evaluation of novel benzophenone-thiazole derivatives as potent VEGF-A inhibitors
  作者：T. Prashanth、Prabhu Thirusangu、B.R. Vijay Avin、V. Lakshmi Ranganatha、B.T. Prabhakar、Shaukath Ara Khanum

  DOI：10.1016/j.ejmech.2014.09.069

  日期：2014.11

  A series of 2-(4-benzoyl-phenoxy)-N-(4-phenyl-thiazol-2-yl)-acetamides (10a-n) were synthesized by multistep reaction sequence and all the compounds were well characterized for structural elucidation. The in vitro cytotoxicity of compounds 10a-n was evaluated against EAC and DLA cell lines using trypan blue dye exclusion method. Further MTT assay and LDH release assay, followed by in vivo studies on murine model were also evaluated. The compound 10h with a methyl and fluor groups at benzophenone moiety and methoxy group at phenyl ring was in a leading position to exhibit the promising antiproliferative effect through translational VEGF-A inhibition. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Benzophenone-N-ethyl piperidine ether analogues—Synthesis and efficacy as anti-inflammatory agent
  作者：Shaukath A. Khanum、V. Girish、S.S. Suparshwa、Noor Fatima Khanum

  DOI：10.1016/j.bmcl.2009.02.070

  日期：2009.4

  A sequence of substituted benzophenone-N-ethyl piperidine ether analogues has been synthesized and evaluated as orally active anti-inflammatory agents with reduced side effects. The anti-inflammatory and ulcerogenic activities of the compounds were compared with naproxen, indomethacin, and phenylbutazone. These analogues showed an interesting anti-inflammatory activity in carrageenan-induced foot pad edema assay. In the air-pouch test, some of the analogues reduced the total number of leukocytes of the exudate, which indicates inhibition of prostaglandin production. Side effects of the compounds were examined on gastric mucosa, in the liver and stomach. None of the compounds illustrated significant side effects compared with standard drugs like indomethacin and naproxen. (C) 2009 Elsevier Ltd. All rights reserved.
• Design and synthesis of 1-(4-benzoylphenyl)imidazole derivatives as new potent 20-HETE synthase inhibitors
  作者：Toshio Nakamura、Takaaki Ishii、Noriyuki Miyata、Kazuo Taniguchi、Yasumitsu Tomishima、Tomokazu Ueki、Masakazu Sato

  DOI：10.1016/j.bmcl.2004.08.025

  日期：2004.11

  Structural modification of the novel 20-HETE synthase inhibitor 1 (IC50 310nM) is described. Introduction of a side chain with a carboxylic acid at the terminal position to 1 resulted in increased ability to inhibit human renal microsomal production of 20-HETE (7c: IC50 7.9 nM), with good selectivity toward CYP2D6 and cyclooxygenases (COX)-1 and -2. (C) 2004 Elsevier Ltd. All rights reserved.