2-(3-Fluorophenoxy)-1-phenyl-ethanone | 1154637-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-Fluorophenoxy)-1-phenyl-ethanone
• 英文别名: 2-(3-fluorophenoxy)-1-phenylethanone
• CAS: 1154637-56-5
• 化学式: C₁₄H₁₁FO₂
• mdl: MFCD12645324
• 分子量: 230.239
• InChiKey: CWPPUUOELSUMAG-UHFFFAOYSA-N

物化性质

• 沸点：
  352.7±22.0 °C(predicted)
• 密度：
  1.189±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-Fluorophenoxy)-1-phenyl-ethanone 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以91%的产率得到(NZ)-N-[2-(3-fluorophenoxy)-1-phenylethylidene]hydroxylamine
  参考文献：
  名称：

  Replacement of the Methylene of Dihydrochalcones with Oxygen: Synthesis and Biological Evaluation of 2-Phenoxyacetophenones

  摘要：

  With the aim of finding new bioactive compounds, a series of phenoxyacetophenone derivatives 2 were designed and synthesized as oxygen analogs of dihydrochalcones. Also, phenoxyacetophenones were converted to (Z)‐oxime derivatives 3 and their geometry were characterized by 1H‐NMR spectroscopy. The in vitro antifungal activity of compounds 2 and 3 was evaluated against Candida albicans, Candida glabrata, Saccharomyces cerevisiae, and Aspergillus niger using micro‐dilution method. In general, oxime derivative 3d containing 4‐fluorophenoxy moiety showed comparable or more potent antifungal activity (MICs = 15.63–31.25 μg/mL) with respect to the reference drug fluconazole against all tested yeasts. In addition, the antileishmanial activity of title compounds was determined against pormastigote form of Leishmania major. All compounds showed mild growth inhibitory activity against promastigotes. The most active compound was unsubstituted phenoxyacetophenone 2a (IC50 = 80 μg/mL). To anticipate the potential use as drugs, the target compounds were evaluated in their drug‐like properties. The in silico values of molecular descriptors for bioactive compounds 2a and 3d revealed that these compounds are within the range set by Lipinski’s ‘Rule of 5’ and show no violation of these rules. Moreover, bioactive compounds 2a and 3d are supposed to be non‐mutagenic and non‐tumorigenic, with no irritating or reproductive effects.

  DOI：

  10.1111/j.1747-0285.2012.01432.x
• 作为产物：
  描述：

  苯乙酮 在 potassium carbonate 、 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(3-Fluorophenoxy)-1-phenyl-ethanone
  参考文献：
  名称：

  新系列芳氧基苯乙酮缩氨基硫脲的合成和体外抗弓形虫活性。

  摘要：

  合成了一系列新的芳氧基苯乙酮缩氨基硫脲 4a-q 作为抗弓形虫剂。所有化合物均显示出对弓形虫感染细胞的显着抑制活性（IC50 值为 1.09-25.19 μg/mL）。4-氟苯氧基衍生物 (4l) 是最有效的化合物，对宿主细胞的选择性最高 (SI = 19)，优于标准药物乙胺嘧啶。SAR 研究表明，苯氧基苯乙酮的两个芳环上适当取代基的同时出现对效力和安全性很重要。对代表性化合物 4l 和 4p 的进一步体外实验表明，这些化合物在 5 μg/mL 的浓度下可以显着降低刚地弓形虫速殖子的活力，以及它们的感染率和细胞内增殖，与乙胺嘧啶相当。

  DOI：

  10.1007/s11030-019-09986-9

文献信息

• Replacement of the Methylene of Dihydrochalcones with Oxygen: Synthesis and Biological Evaluation of 2-Phenoxyacetophenones
  作者：Mahsa Ansari、Saeed Emami、Mohammad A. Khalilzadeh、Malek T. Maghsoodlou、Alireza Foroumadi、Mohammad A. Faramarzi、Nasrin Samadi、Sussan K. Ardestani

  DOI：10.1111/j.1747-0285.2012.01432.x

  日期：2012.10

  With the aim of finding new bioactive compounds, a series of phenoxyacetophenone derivatives 2 were designed and synthesized as oxygen analogs of dihydrochalcones. Also, phenoxyacetophenones were converted to (Z)‐oxime derivatives 3 and their geometry were characterized by 1H‐NMR spectroscopy. The in vitro antifungal activity of compounds 2 and 3 was evaluated against Candida albicans, Candida glabrata, Saccharomyces cerevisiae, and Aspergillus niger using micro‐dilution method. In general, oxime derivative 3d containing 4‐fluorophenoxy moiety showed comparable or more potent antifungal activity (MICs = 15.63–31.25 μg/mL) with respect to the reference drug fluconazole against all tested yeasts. In addition, the antileishmanial activity of title compounds was determined against pormastigote form of Leishmania major. All compounds showed mild growth inhibitory activity against promastigotes. The most active compound was unsubstituted phenoxyacetophenone 2a (IC50 = 80 μg/mL). To anticipate the potential use as drugs, the target compounds were evaluated in their drug‐like properties. The in silico values of molecular descriptors for bioactive compounds 2a and 3d revealed that these compounds are within the range set by Lipinski’s ‘Rule of 5’ and show no violation of these rules. Moreover, bioactive compounds 2a and 3d are supposed to be non‐mutagenic and non‐tumorigenic, with no irritating or reproductive effects.
• Synthesis and in vitro anti-Toxoplasma gondii activity of a new series of aryloxyacetophenone thiosemicarbazones
  作者：Mahsa Ansari、Mahbobeh Montazeri、Ahmad Daryani、‬‬‬‬‬‬Kaveh Farshadfar、Saeed Emami

  DOI：10.1007/s11030-019-09986-9

  日期：2020.11

  A new series of aryloxyacetophenone thiosemicarbazones 4a-q have been synthesized as anti-Toxoplasma gondii agents. All compounds showed significant inhibitory activity against T. gondii-infected cells (IC50 values 1.09-25.19 μg/mL). The 4-fluorophenoxy derivative (4l) was the most potent compound with the highest selectivity toward host cells (SI = 19), being better than standard drug pyrimethamine

  合成了一系列新的芳氧基苯乙酮缩氨基硫脲 4a-q 作为抗弓形虫剂。所有化合物均显示出对弓形虫感染细胞的显着抑制活性（IC50 值为 1.09-25.19 μg/mL）。4-氟苯氧基衍生物 (4l) 是最有效的化合物，对宿主细胞的选择性最高 (SI = 19)，优于标准药物乙胺嘧啶。SAR 研究表明，苯氧基苯乙酮的两个芳环上适当取代基的同时出现对效力和安全性很重要。对代表性化合物 4l 和 4p 的进一步体外实验表明，这些化合物在 5 μg/mL 的浓度下可以显着降低刚地弓形虫速殖子的活力，以及它们的感染率和细胞内增殖，与乙胺嘧啶相当。