5-(benzyloxy)-2-(hydroxymethyl)-1-cyclopropylpyridin-4(1H)-one | 1620023-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(benzyloxy)-2-(hydroxymethyl)-1-cyclopropylpyridin-4(1H)-one
• CAS: 1620023-69-9
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: STYDTLWWSQHKED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.46
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-2-(hydroxymethyl)-1-cyclopropylpyridin-4(1H)-one 在 氯化亚砜 、 碳酸氢钠 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 5-(benzyloxy)-2-((4-(7-chloroquinolin-4-ylamino)butylamino)methyl)-1-cyclopropylpyridin-4(1H)-one
  参考文献：
  名称：

  Kojic acid derived hydroxypyridinone–chloroquine hybrids: Synthesis, crystal structure, antiplasmodial activity and β-haematin inhibition

  摘要：

  Aminochloroquinoline-kojic acid hybrids were synthesized and evaluated for p-haematin inhibition and antiplasmodial activity against drug resistant (K1) and sensitive (3D7) strains of Plasmodium falciparum. Compound 7j was the most potent compound in both strains (IC503D7 = 0.004 mu M; IC50K1 = 0.03 mu M) and had the best beta-haematin inhibition activity (0.07 IC50 equiv vs 1.91 IC50 equiv for chloroquine). One compound 8c was found to be equipotent in both strains (IC50 = 0.04 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.012
• 作为产物：
  描述：

  曲酸 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 5-(benzyloxy)-2-(hydroxymethyl)-1-cyclopropylpyridin-4(1H)-one
  参考文献：
  名称：

  Kojic acid derived hydroxypyridinone–chloroquine hybrids: Synthesis, crystal structure, antiplasmodial activity and β-haematin inhibition

  摘要：

  Aminochloroquinoline-kojic acid hybrids were synthesized and evaluated for p-haematin inhibition and antiplasmodial activity against drug resistant (K1) and sensitive (3D7) strains of Plasmodium falciparum. Compound 7j was the most potent compound in both strains (IC503D7 = 0.004 mu M; IC50K1 = 0.03 mu M) and had the best beta-haematin inhibition activity (0.07 IC50 equiv vs 1.91 IC50 equiv for chloroquine). One compound 8c was found to be equipotent in both strains (IC50 = 0.04 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.012