4-[2-hydroxy-3-(2-oxo-2H-chromen-4-yloxy)propylamino]butyric acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[2-hydroxy-3-(2-oxo-2H-chromen-4-yloxy)propylamino]butyric acid
• 英文别名: 4-[[2-Hydroxy-3-(2-oxochromen-4-yl)oxypropyl]amino]butanoic acid；4-[[2-hydroxy-3-(2-oxochromen-4-yl)oxypropyl]amino]butanoic acid
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: RSWMFLKXZFINNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 4-[2-hydroxy-3-(2-oxo-2H-chromen-4-yloxy)propylamino]butyric acid
  参考文献：
  名称：

  Synthesis and biological evaluation of 4-oxycoumarin derivatives as a new class of antifilarial agents

  摘要：

  A series of 4-oxycoumarin derivatives was synthesized, characterized and evaluated in vitro and in vivo for antifilarial activity against the human lymphatic filarial parasite, Brugia malayi. A majority of the compounds studied showed potent in vitro activity with low IC50 values in the micro molar (mu M) range (0.014-1.73 and 0.0056-0.43) against adult worms and microfilariae, respectively. Compounds 8 and 9 were identified to be the most promising antifilarial candidate molecules exhibiting activity in the nanomolar (nM) range. The IC50 values for compound 8 were 14 nM and 5.6 nM while for compound 9 were 94 nM and 13 nM, respectively, for adult worm and microfilaria. These two compounds also displayed promising adulticidal activity (74.9 +/- 4.8% and 69.4 +/- 2.8%, respectively) in the primary rodent (jird) screen. This study also serves as a starting point for investigating structure-activity relationship with different amino substituents. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.043

文献信息

• Synthesis and biological evaluation of 4-oxycoumarin derivatives as a new class of antifilarial agents
  作者：Sweta Misra、Lav Kumar Singh、Priyanka、Jyoti Gupta、Shailja Misra-Bhattacharya、Diksha Katiyar

  DOI：10.1016/j.ejmech.2015.02.043

  日期：2015.4

  A series of 4-oxycoumarin derivatives was synthesized, characterized and evaluated in vitro and in vivo for antifilarial activity against the human lymphatic filarial parasite, Brugia malayi. A majority of the compounds studied showed potent in vitro activity with low IC50 values in the micro molar (mu M) range (0.014-1.73 and 0.0056-0.43) against adult worms and microfilariae, respectively. Compounds 8 and 9 were identified to be the most promising antifilarial candidate molecules exhibiting activity in the nanomolar (nM) range. The IC50 values for compound 8 were 14 nM and 5.6 nM while for compound 9 were 94 nM and 13 nM, respectively, for adult worm and microfilaria. These two compounds also displayed promising adulticidal activity (74.9 +/- 4.8% and 69.4 +/- 2.8%, respectively) in the primary rodent (jird) screen. This study also serves as a starting point for investigating structure-activity relationship with different amino substituents. (C) 2015 Elsevier Masson SAS. All rights reserved.