(NZ)-N-[1-phenyl-2-(3,4,5-trimethoxyphenoxy)ethylidene]hydroxylamine | 1408323-59-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (NZ)-N-[1-phenyl-2-(3,4,5-trimethoxyphenoxy)ethylidene]hydroxylamine
• CAS: 1408323-59-0
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: LZYDJFLRSXOBFY-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  69.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-phenyl-2-(3,4,5-trimethoxyphenoxy)ethanone 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以64%的产率得到(NZ)-N-[1-phenyl-2-(3,4,5-trimethoxyphenoxy)ethylidene]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

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.