N-mycophenoyl-L-phenylalanine

• 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: N-mycophenoyl-L-phenylalanine
• 英文别名: (2S)-2-[[(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoyl]amino]-3-phenylpropanoic acid
• 化学式: C₂₆H₂₉NO₇
• 分子量: 467.519
• InChiKey: SPTFSNWAKOEDBG-ULXKQSRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl ester N-mycophenoyl-L-phenylalanine 在 lithium hydroxide monohydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以59%的产率得到N-mycophenoyl-L-phenylalanine
  参考文献：
  名称：

  Synthesis and biological activity of mycophenolic acid-amino acid derivatives

  摘要：

  In search of new immunosuppressants we synthesized 11 amino acids derivatives of MPA as methyl esters 10a-k using EDCl/DMAP and their corresponding amino acid derivatives in free acid form ha k by hydrolysis of ester group with LiOH/MeOH. New analogs were evaluated as growth inhibitors of lymphoid cell line (Jurkat) and human peripheral blood mononuclear cells (PBMC) from healthy donors. According to obtained results recovering of free carboxylic group increased their activity. Additionally, the cytotoxic properties depends on the substituent and configuration at chiral center in amino acid unit. The compounds 10j, lie and 11h exhibited higher potency than MPA 1 in vitro. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.026

文献信息

• Synthesis and biological activity of mycophenolic acid-amino acid derivatives
  作者：Dorota Iwaszkiewicz-Grzes、Grzegorz Cholewinski、Agata Kot-Wasik、Piotr Trzonkowski、Krystyna Dzierzbicka

  DOI：10.1016/j.ejmech.2013.09.026

  日期：2013.11

  In search of new immunosuppressants we synthesized 11 amino acids derivatives of MPA as methyl esters 10a-k using EDCl/DMAP and their corresponding amino acid derivatives in free acid form ha k by hydrolysis of ester group with LiOH/MeOH. New analogs were evaluated as growth inhibitors of lymphoid cell line (Jurkat) and human peripheral blood mononuclear cells (PBMC) from healthy donors. According to obtained results recovering of free carboxylic group increased their activity. Additionally, the cytotoxic properties depends on the substituent and configuration at chiral center in amino acid unit. The compounds 10j, lie and 11h exhibited higher potency than MPA 1 in vitro. (C) 2013 Elsevier Masson SAS. All rights reserved.