6-(chloromethyl)-3-hydroxy-2-({4-[4-(trifluoromethyl)phenyl]piperazin-1-yl}methyl)-4H-pyran-4-one | 1225388-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-(chloromethyl)-3-hydroxy-2-({4-[4-(trifluoromethyl)phenyl]piperazin-1-yl}methyl)-4H-pyran-4-one
• 英文别名: 6-(Chloromethyl)-3-hydroxy-2-[[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]pyran-4-one；6-(chloromethyl)-3-hydroxy-2-[[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]pyran-4-one
• CAS: 1225388-70-4
• 化学式: C₁₈H₁₈ClF₃N₂O₃
• 分子量: 402.801
• InChiKey: GQBZKLIASIUGHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  曲酸 在 氯化亚砜 作用下， 以 甲醇 、 水 为溶剂， 反应 0.42h， 生成 6-(chloromethyl)-3-hydroxy-2-({4-[4-(trifluoromethyl)phenyl]piperazin-1-yl}methyl)-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis and biological activities of new Mannich bases of chlorokojic acid derivatives

  摘要：

  A novel series of 6-chloromethyl-3-hydroxy-2-substituted 4H-pyran-4-one derivatives were synthesized and tested for their antibacterial, antifungal and antiviral in vitro properties. In the view of activity results, compounds 8-11 (MIC: 8 mu g/ml) were more remarkably active against Staphylococcus aureus and Enterococcus faecalis. Compounds 1-7 were highly active against Candida albicans and C. parapsilosis with MIC value of 8 mu g/ml. Compound 9 bearing 3-chlorophenyl moiety was determined to be the most active compound against RNA virus PI-3.

  DOI：

  10.1007/s00044-010-9338-x

文献信息

• Synthesis and biological activities of new Mannich bases of chlorokojic acid derivatives
  作者：Mutlu Dilsiz Aytemir、Berrin Özçelik

  DOI：10.1007/s00044-010-9338-x

  日期：2011.5

  A novel series of 6-chloromethyl-3-hydroxy-2-substituted 4H-pyran-4-one derivatives were synthesized and tested for their antibacterial, antifungal and antiviral in vitro properties. In the view of activity results, compounds 8-11 (MIC: 8 mu g/ml) were more remarkably active against Staphylococcus aureus and Enterococcus faecalis. Compounds 1-7 were highly active against Candida albicans and C. parapsilosis with MIC value of 8 mu g/ml. Compound 9 bearing 3-chlorophenyl moiety was determined to be the most active compound against RNA virus PI-3.
• Evaluation of bioactivities of chlorokojic acid derivatives against dermatophytes couplet with cytotoxicity
  作者：Mutlu Dilsiz Aytemir、Berrin Özçelik、Gülşah Karakaya

  DOI：10.1016/j.bmcl.2013.03.098

  日期：2013.6

  In an attempt to find novel antifungal agents with improved activity, a series of compounds bearing 6-chloromethyl-3-hydroxy-2-substituted 4H-pyran-4-one moiety were synthesized and examined for their cytotoxic evaluation and antifungal activities against both standard and isolated dermatophytic fungal species Microsporum gypseum, Trichophyton mentagrophytes var. erinacei and Epidermophyton floccosum. (C) 2013 Elsevier Ltd. All rights reserved.