N-(all-trans-retinoyl)-L-leucine | 110769-97-6

• 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-(all-trans-retinoyl)-L-leucine
• 英文别名: N-(all-trans-retinoyl)leucine；(2S)-2-[[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]-4-methylpentanoic acid
• CAS: 110769-97-6
• 化学式: C₂₆H₃₉NO₃
• 分子量: 413.601
• InChiKey: XILISIALPJYAMY-NYIXRIPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  维A酸 在 氢氧化钾 、 三氯化磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 2.0h， 生成 N-(all-trans-retinoyl)-L-leucine
  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

文献信息

• Effect of conjugates of all-trans-retinoic acid and shorter polyene chain analogues with amino acids on prostate cancer cell growth
  作者：Eldem Sadikoglou、George Magoulas、Christina Theodoropoulou、Constantinos M. Athanassopoulos、Efstathia Giannopoulou、Olga Theodorakopoulou、Denis Drainas、Dionysios Papaioannou、Evangelia Papadimitriou

  DOI：10.1016/j.ejmech.2009.03.029

  日期：2009.8

  cells. In contrast to ATRA, all conjugates bearing amino acids with polar side chains showed no inhibitory effect on LNCaP cell proliferation, while conjugates with α-amino acids with lipophilic side chain, such as 7, or linear amino acids, such as 9, significantly decreased prostate cancer LNCaP cell number. Interestingly, while the effect of ATRA was RARα-dependent, the effect of its active analogues

  在本工作中，通过将酸性类维生素A的琥珀酰亚胺基活性酯与适当保护的氨基酸或肽偶联，合成了一系列氨基酸与全反式维甲酸（ATRA）和较短的多烯链类似物的共轭物。通过脱保护，并检查其对人前列腺癌LNCaP细胞活力的可能影响。与ATRA相反，所有带有极性侧链氨基酸的结合物对LNCaP细胞的增殖均无抑制作用，而带有亲脂性侧链的α-氨基酸（例如7）或线性氨基酸（例如9）的结合物，显着降低了前列腺癌LNCaP细胞的数量。有趣的是，尽管ATRA的作用是RARα依赖性的，但其活性类似物的作用并未受到选择性RARα拮抗剂的抑制。细胞周期分析显示对细胞周期没有影响，而膜联蛋白V-碘化丙啶染色的定量分析表明，ATRA及其类似物均不影响LNCaP细胞凋亡或坏死。这些结果表明，化合物7和9是潜在有用的试剂，需要进一步的临床前开发以治疗前列腺癌。
• SHEALY, Y. FULMER;FRYE, JERRY L.;SCHIFF, LEONARD J., J. MED. CHEM., 31,(1988) N 1, 190-196
  作者：SHEALY, Y. FULMER、FRYE, JERRY L.、SCHIFF, LEONARD J.

  DOI：——

  日期：——
• N-(Retinoyl) amino acids. Synthesis and chemopreventive activity in vitro
  作者：Y. Fulmer Shealy、Jerry L. Frye、Leonard J. Schiff

  DOI：10.1021/jm00396a031

  日期：1988.1

  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.