N-(13-cis-retinoyl)glycine ethyl ester | 110848-61-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(13-cis-retinoyl)glycine ethyl ester
• CAS: 110848-61-8
• 化学式: C₂₄H₃₅NO₃
• 分子量: 385.547
• InChiKey: XQUXHEMMWYKMRG-UUEAIZLISA-N

物化性质

• 沸点：
  557.7±42.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(13-cis-retinoyl)glycine ethyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以80%的产率得到2-[[(2Z,4E,6E,8E)-3,7-二甲基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酰基]氨基]乙酸
  参考文献：
  名称：

  N-(Retinoyl) amino acids. Synthesis and chemopreventive activity in vitro

  摘要：

  N-(all-trans-Retinoyl)amino acids were synthesized via all-trans-retinoyl chloride and an ester of the amino acid. The retinoyl derivatives of leucine, phenylalanine, alanine, tyrosine, and glutamic acid were prepared. The 13-cis-retinoyl derivatives of leucine, phenylalanine, alanine, and glycine were prepared similarly from 13-cis-retinoic acid. In assays of the retinoylamino acids for reversal of squamous metaplasia in hamster trachea organ cultures, these compounds were less active than retinoic acid, but the leucine, alanine, and phenylalanine derivatives were similar in activity to several retinamides that suppress bladder carcinogenesis in vivo. Two of the retinoylamino acids, as well as two simple retinamides, were shown to be moderately cytotoxic to murine leukemia and human epidermoid carcinoma cells in culture.

  DOI：

  10.1021/jm00396a031
• 作为产物：
  描述：

  异维A酸 在 三氯化磷 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 2.5h， 生成 N-(13-cis-retinoyl)glycine ethyl ester
  参考文献：
  名称：

  N-(Retinoyl) amino acids. Synthesis and chemopreventive activity in vitro

  摘要：

  N-(all-trans-Retinoyl)amino acids were synthesized via all-trans-retinoyl chloride and an ester of the amino acid. The retinoyl derivatives of leucine, phenylalanine, alanine, tyrosine, and glutamic acid were prepared. The 13-cis-retinoyl derivatives of leucine, phenylalanine, alanine, and glycine were prepared similarly from 13-cis-retinoic acid. In assays of the retinoylamino acids for reversal of squamous metaplasia in hamster trachea organ cultures, these compounds were less active than retinoic acid, but the leucine, alanine, and phenylalanine derivatives were similar in activity to several retinamides that suppress bladder carcinogenesis in vivo. Two of the retinoylamino acids, as well as two simple retinamides, were shown to be moderately cytotoxic to murine leukemia and human epidermoid carcinoma cells in culture.

  DOI：

  10.1021/jm00396a031