N-(all-trans-Retinoyl)-morpholine

• 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)-morpholine
• 英文别名: (2E,4E,6E,8E)-3,7-dimethyl-1-morpholino-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-one；3,7-dimethyl-1-morpholin-4-yl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-1-one；(2E,4E,6E,8E)-3,7-dimethyl-1-morpholin-4-yl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-one
• 化学式: C₂₄H₃₅NO₂
• 分子量: 369.547
• InChiKey: XHPKRVYZMVFULC-SFZCRTJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吗啉 、 维A酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以9%的产率得到N-(all-trans-Retinoyl)-morpholine
  参考文献：
  名称：

  Fenretinide Derivatives Act as Disrupters of Interactions of Serum Retinol Binding Protein (sRBP) with Transthyretin and the sRBP Receptor

  摘要：

  Serum retinol binding protein (sRBP) is released from the liver as a complex with transthyretin (TTR), a process under the control of dietary retinol. Elevated levels of sRBP may be involved in inhibiting cellular responses to insulin and in generating first insulin resistance and then type 2 diabetes, offering a new target for therapeutic attack for these conditions. A series of retinoid analogues were synthesized and examined for their binding to sRBP and their ability to disrupt the sRBP-TTR and sRBP-sRBP receptor interactions. A number inhibit the sRBP-TTR and sRBP-sRBP receptor interactions as well as or better than Fenretinide (FEN), presenting a potential novel dual mechanism of action and perhaps offering a new therapeutic intervention against type 2 diabetes and its development. Shortening the chain length of the FEN derivative substantially abolished binding to sRBP, indicating that the strength of the interaction the polyene chain region. Differences in potency against the sRBP-TTR and sRBP-sRBP receptor interactions suggest variant effects of the compounds on the two loops of sRBP guarding the entrance of the binding pocket that are responsible for these two protein-protein interactions.

  DOI：

  10.1021/jm200256g

文献信息

• Amino, Amino Acid or Peptide Conjugates of Retinoic Acid
  申请人：Beumer Raphael

  公开号：US20070270472A1

  公开（公告）日：2007-11-22

  The invention provides the use of retinoyl derivatives for the cosmetic treatment or prophylaxis of wrinkles, skin aging and/or for thickening the epidermis.

  本发明提供了利用维甲酸酯类化合物进行美容治疗或预防皱纹、皮肤老化和/或增厚表皮的方法。
• Composition pour induire et stimuler la croissance des cheveux et/ou freiner leur chute, à base de dérivés de pyrimidine et de filtres solaires
  申请人：L'OREAL

  公开号：EP0376821B1

  公开（公告）日：1992-08-26
• US4055659A
  申请人：——

  公开号：US4055659A

  公开（公告）日：1977-10-25
• US4126693A
  申请人：——

  公开号：US4126693A

  公开（公告）日：1978-11-21
• US4126697A
  申请人：——

  公开号：US4126697A

  公开（公告）日：1978-11-21