N3-(4-methoxyfumaroyl)-(L)-2,3-diaminopropanoic acid [(2-ethylbutanoyl)oxy]methyl ester trifluoroacetate | 1367293-17-1

• 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: N3-(4-methoxyfumaroyl)-(L)-2,3-diaminopropanoic acid [(2-ethylbutanoyl)oxy]methyl ester trifluoroacetate
• CAS: 1367293-17-1
• 化学式: C₂HF₃O₂*C₁₅H₂₄N₂O₇
• 分子量: 458.389
• InChiKey: FNQLNWZSEOLBGS-OPRTUBLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  171.32
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  、 N3-(4-methoxyfumaroyl)-(L)-2,3-diaminopropanoic acid [(2-ethylbutanoyl)oxy]methyl ester trifluoroacetate 在 盐酸 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 为溶剂， 反应 14.5h， 以0.26 g的产率得到N2-(bis-N,N-(2-acetoxyethyl)glycinyl)-N3-(4-methoxyfumaroyl)-(L)-2,3-diaminopropanoic acid [(2-ethylbutanoyl)oxy]methyl ester hydrochloride
  参考文献：
  名称：

  The synthesis and biological activity of lipophilic derivatives of bicine conjugated withN³-(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid (FMDP)—an inhibitor of glucosamine-6-phosphate synthase

  摘要：

  A series of bis-N,N-(2-hydroxyethyl)glycine (bicine) derivatives, conjugated with an inhibitor of glucosamine-6-phosphate synthase, have been synthesized and their lipophilic and antifungal properties have been tested. The obtained compounds demonstrated higher lipophilicity than free inhibitor (FMDP) and, in consequence, an increased potential to cross the cytoplasmic membrane. All the tested compounds show better antifungal activity than parent compound.

  DOI：

  10.3109/14756366.2011.582039
• 作为产物：
  描述：

  2-乙基丁酸氯甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 N3-(4-methoxyfumaroyl)-(L)-2,3-diaminopropanoic acid [(2-ethylbutanoyl)oxy]methyl ester trifluoroacetate
  参考文献：
  名称：

  The synthesis and biological activity of lipophilic derivatives of bicine conjugated withN³-(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid (FMDP)—an inhibitor of glucosamine-6-phosphate synthase

  摘要：

  A series of bis-N,N-(2-hydroxyethyl)glycine (bicine) derivatives, conjugated with an inhibitor of glucosamine-6-phosphate synthase, have been synthesized and their lipophilic and antifungal properties have been tested. The obtained compounds demonstrated higher lipophilicity than free inhibitor (FMDP) and, in consequence, an increased potential to cross the cytoplasmic membrane. All the tested compounds show better antifungal activity than parent compound.

  DOI：

  10.3109/14756366.2011.582039