(3S,4R,5R)-3-Amino-5-((E)-hexadec-2-enyl)-4-hydroxy-3-hydroxymethyl-dihydro-furan-2-one | 184001-24-9

• 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: (3S,4R,5R)-3-Amino-5-((E)-hexadec-2-enyl)-4-hydroxy-3-hydroxymethyl-dihydro-furan-2-one
• 英文别名: (3S,4R,5R)-3-amino-5-[(E)-hexadec-2-enyl]-4-hydroxy-3-(hydroxymethyl)oxolan-2-one
• CAS: 184001-24-9
• 化学式: C₂₁H₃₉NO₄
• 分子量: 369.545
• InChiKey: CAJHAXBDCHQHDI-QRPXNZHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-3-Amino-5-((E)-hexadec-2-enyl)-4-hydroxy-3-hydroxymethyl-dihydro-furan-2-one 在 咪唑 、 sodium acetate 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 [(3S,5R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-5-((E)-hexadec-2-enyl)-2,4-dioxo-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Potent Immunosuppressants, 2-Alkyl-2-aminopropane-1,3-diols

  摘要：

  Several immunosuppressants, ISP-I [(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoeicos-6-enoic acid, myriocin = thermozymocidin] and mycestericins A-G, were isolated from culture broths of Isaria sinclairii and Mycelia sterilia, respectively. In order to investigate structure-activity relationships, extensive modifications of ISP-I were conducted, and it was established that the fundamental structure possessing the immunosuppressive activity is a symmetrical 2-alkyl-2-aminopropane-1,3-diol. The tetradecyl, pentadecyl, and hexadecyl derivatives prolonged rat skin allograft, survival in the combination of LEW donor and F344 recipient and were more effective than cyclosporin A. Among them, 2-amino-2-tetradecylpropane-1,3-diol hydrochloride, ISP-I-55, showed the lowest toxicity. ISP-I-55 is a promising lead compound for the development of effective immunosuppressants for organ transplantations and for the treatment of autoimmune diseases.

  DOI：

  10.1021/jm960391l
• 作为产物：
  描述：

  14-deoxomyriocin 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以79.2%的产率得到(3S,4R,5R)-3-Amino-5-((E)-hexadec-2-enyl)-4-hydroxy-3-hydroxymethyl-dihydro-furan-2-one
  参考文献：
  名称：

  Potent Immunosuppressants, 2-Alkyl-2-aminopropane-1,3-diols

  摘要：

  Several immunosuppressants, ISP-I [(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoeicos-6-enoic acid, myriocin = thermozymocidin] and mycestericins A-G, were isolated from culture broths of Isaria sinclairii and Mycelia sterilia, respectively. In order to investigate structure-activity relationships, extensive modifications of ISP-I were conducted, and it was established that the fundamental structure possessing the immunosuppressive activity is a symmetrical 2-alkyl-2-aminopropane-1,3-diol. The tetradecyl, pentadecyl, and hexadecyl derivatives prolonged rat skin allograft, survival in the combination of LEW donor and F344 recipient and were more effective than cyclosporin A. Among them, 2-amino-2-tetradecylpropane-1,3-diol hydrochloride, ISP-I-55, showed the lowest toxicity. ISP-I-55 is a promising lead compound for the development of effective immunosuppressants for organ transplantations and for the treatment of autoimmune diseases.

  DOI：

  10.1021/jm960391l