4-[3-hydroxy-4-(piperidin-1-ylmethyl)phenyl]butan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-[3-hydroxy-4-(piperidin-1-ylmethyl)phenyl]butan-2-one
• 英文别名: 4-[3-Hydroxy-4-(piperidin-1-ylmethyl)phenyl]butan-2-one
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: AFFODWKGHGFDNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  哌啶 、 聚合甲醛 、 4-(3-hydroxyphenyl)butan-2-one 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 9.0h， 以84%的产率得到4-[3-hydroxy-4-(piperidin-1-ylmethyl)phenyl]butan-2-one
  参考文献：
  名称：

  Syntheses and in Vitro Antiplasmodial Activity of Aminoalkylated Chalcones and Analogues

  摘要：

  A series of readily synthesized and inexpensive aminoalkylated chalcones and diarylpropane analogues (1-55) were synthesized and tested against chloroquinone-sensitive (D10 and NF54) and -resistant (Dd2 and K1) strains of Plasmodium falciparum. Hydrogenation of the enone to a diarylpropane moiety increased antiplasmodial bioactivity significantly. The influence of the structure of the amine moiety, A-ring substituents, propyl vs ethyl linker, and chloride salt formation on further enhancing antiplasmodial activity was investigated. Several compounds have IC50 values similar to or better than chloroquine (CQ). The most active compound (26) had an IC50 value of 0.01 mu M. No signs of resistance were detected, as can be expected from compounds with structures unrelated to CQ and other currently used antimalarial drugs. Toxicity tests (in vitro CHO cell assay) gave high SI indices.

  DOI：

  10.1021/acs.jnatprod.5b00114

文献信息

• Syntheses and in Vitro Antiplasmodial Activity of Aminoalkylated Chalcones and Analogues
  作者：Anke Wilhelm、Pravin Kendrekar、Anwar E. M. Noreljaleel、Efrem T. Abay、Susan L. Bonnet、Lubbe Wiesner、Carmen de Kock、Kenneth J. Swart、Jan Hendrik van der Westhuizen

  DOI：10.1021/acs.jnatprod.5b00114

  日期：2015.8.28

  A series of readily synthesized and inexpensive aminoalkylated chalcones and diarylpropane analogues (1-55) were synthesized and tested against chloroquinone-sensitive (D10 and NF54) and -resistant (Dd2 and K1) strains of Plasmodium falciparum. Hydrogenation of the enone to a diarylpropane moiety increased antiplasmodial bioactivity significantly. The influence of the structure of the amine moiety, A-ring substituents, propyl vs ethyl linker, and chloride salt formation on further enhancing antiplasmodial activity was investigated. Several compounds have IC50 values similar to or better than chloroquine (CQ). The most active compound (26) had an IC50 value of 0.01 mu M. No signs of resistance were detected, as can be expected from compounds with structures unrelated to CQ and other currently used antimalarial drugs. Toxicity tests (in vitro CHO cell assay) gave high SI indices.