methyl 1-[2-(furan-2-yl)-2-oxoethyl]-5-oxopyrrolidine-2-carboxylate

• 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: methyl 1-[2-(furan-2-yl)-2-oxoethyl]-5-oxopyrrolidine-2-carboxylate
• 英文别名: Methyl 1-[2-(furan-2-yl)-2-oxoethyl]-5-oxopyrrolidine-2-carboxylate
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: ZIBXGQZPYZZQRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  76.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  licochalcone A 在 transgenic crown galls of Panax quinquefolium 作用下， 以 甲醇 为溶剂， 反应 168.0h， 以4.5 mg的产率得到methyl 1-[(5-formylfuran-2-yl)methyl]-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  Biotransformation of Licochalcone A by transgenic crown galls of Panax quinquefolium

  摘要：

  Licochalcone A, as main constituent of Chinese Gancao (Glycyrrhiza inflate Bat), is responsible for the chemopreventive effect of the herbal. In order to get the bioactive modified molecules of Licochalcone A, it was biotransformed using transgenic crown galls of Panax quinquefolium to afford 9 products including a new alkaloid together with 8 known compounds. Their structures were elucidated by physicochemical and spectral methods as: methyl(12S)-1-[(5-formylfuran-2-yl)methy1]-5-oxopyrrolidine-2-carboxylate (1), methyl(12S)-1- [2-(furan-2-y1)-2-oxoethy1]-5-oxopyrrolidine-2-carboxylate (2), 5-hydroxymethy12-furfural (3), (S)-methylpyroglutamate (4), 4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-y1) benzaldehyde (5), 4-hydroxybenzoicacid (6), dibutyl phthalate (7), 3 beta,6 alpha,12 beta,25-tetrahydroxy-(20S,24R)epoxy-dammarane (8)beta-sitosterol (9).Among them, compounds 5 and 6 were transformed from Licochalcone A, while 1-4 and 8 were derived from the culture medium stimulated by the substrate. Furthermore, their cancer chemopreventive effect were tested by the assay of NQ01 (NAD(P)H: quinine oxidoreductase 1) inducing activities in Hepa lcl c cells. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.09.015