(+)-threo-1,3-Dihydroxy-2-amino-eicosan | 3530-52-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+)-threo-1,3-Dihydroxy-2-amino-eicosan
• 英文别名: L-threo-C20-sphinganine；(2S,3S)-2-aminoicosane-1,3-diol
• CAS: 3530-52-7；20180-62-5；24006-62-0；24028-07-7；91685-44-8；98575-69-0；122087-64-3
• 化学式: C₂₀H₄₃NO₂
• 分子量: 329.567
• InChiKey: UFMHYBVQZSPWSS-PMACEKPBSA-N

物化性质

• 沸点：
  471.9±25.0 °C(Predicted)
• 密度：
  0.920±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿:甲醇(5:1)：可溶；乙醇：可溶，温热下溶解

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  23
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硬脂烷醛 在 镍 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (+)-threo-1,3-Dihydroxy-2-amino-eicosan
  参考文献：
  名称：

  鞘脂系列研究（十七）：赤型和苏-C 20-二氢鞘氨醇的合成与拆分

  摘要：

  通过向硝基十八醇中添加硝基乙醇，然后还原赤型和苏型硝基二醇，得到了赤型和苏型-1,3-二羟基-2-氨基二十二烷。用1-谷氨酸拆分得到碱的四种旋光形式。d-构型已分配给+-赤型异构体。

  DOI：

  10.1016/0040-4020(61)80099-9

文献信息

• Compositions and methods for treating hyperproliferative disorders
  申请人：TEXAS TECH UNIVERSITY

  公开号：EP2669267A1

  公开（公告）日：2013-12-04

  A method of treating a hyperproliferative disorder in a subject in need of such treatment, comprising administering to said subject, in combination, a treatment effective amount of: (a) a ceramide-increasing retinoid such as fenretinide or a pharmaceutically acceptable salt thereof; and (b) at least one (and in certain embodiments at least two) compounds selected from the groups consisting of (i) a non-18 carbon chain length L-threo-sphinganine(s) or pharmaceuticeutically acceptable salt thereof, (ii) glucosylceramide or glucosyl(dihydro)ceramide synthesis inhibitor(s), and (iii) sphingomyelin or dihydrosphingomyelin synthase inhibitor(s). Preferred L-threo-sphinganines are of carbon chain length 17 carbons, 19 carbons and 20 carbons. A preferred glucosylceramide or glucosyl(dihydro)ceramide synthesis inhibitor is D-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol.; A preferred sphingomyelin or dihydrosphingomyelin synthesis inhibitor is D-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol. A preferred hyperproliferative disorder is brain cancers.

  一种治疗需要这种治疗的受试者的过度增殖性疾病的方法，包括向所述受试者联合施用治疗有效量的以下物质：(a) 神经酰胺增加型维甲酸，如芬瑞替尼或其药学上可接受的盐；(b) 至少一种（在某些实施方案中至少两种）选自以下组别的化合物：(i) 非 18 碳链长度的 L-苏-鞘氨醇或其药学上可接受的盐；(ii) 葡萄糖甘油酰胺或葡萄糖（二氢）神经酰胺合成抑制剂；(iii) 鞘磷脂或二氢鞘磷脂合成酶抑制剂。优选的 L-硫代鞘磷脂的碳链长度为 17 碳、19 碳和 20 碳。一种优选的葡糖基甘油酰胺或葡糖基（二氢）神经酰胺合成抑制剂是 D-苏-1-苯基-2-棕榈酰氨基-3-吗啉基-1-丙醇；一种优选的鞘磷脂或二氢鞘磷脂合成抑制剂是 D-苏-1-苯基-2-棕榈酰氨基-3-吗啉基-1-丙醇。一种优选的过度增殖性疾病是脑癌。
• COMPOSITIONS AND METHODS FOR TREATING HYPERPROLIFERATIVE DISORDERS
  申请人：TEXAS TECH UNIVERSITY

  公开号：EP2501672A2

  公开（公告）日：2012-09-26
• Compositions and Methods for Treating Hyperproliferative Disorders
  申请人：Maurer Barry James

  公开号：US20110152267A1

  公开（公告）日：2011-06-23

  A method of treating a hyperproliferative disorder in a subject in need of such treatment, comprising administering to said subject, in combination, a treatment effective amount of: (a) a ceramide-increasing retinoid such as fenretinide or a pharmaceutically acceptable salt thereof; and (b) at least one (and in certain embodiments at least two) compounds selected from the groups consisting of (i) a non-18 carbon chain length L-threo-sphinganine(s) or pharmaceuticeutically acceptable salt thereof, (ii) glucosylceramide or glucosyl(dihydro)ceramide synthesis inhibitor(s), and (iii) sphingomyelin or dihydrosphingomyelin synthase inhibitor(s). Preferred L-threo-sphinganines are of carbon chain length 17 carbons, 19 carbons and 20 carbons. A preferred glucosylceramide or glucosyl(dihydro)ceramide synthesis inhibitor is D-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol. A preferred sphingomyelin or dihydrosphingomyelin synthesis inhibitor is D-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol. A preferred hyperproliferative disorder is brain cancers.
• [EN] COMPOSITIONS AND METHODS FOR TREATING HYPERPROLIFERATIVE DISORDERS<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT DE TROUBLES HYPERPROLIFÉRATIFS
  申请人：UNIV TEXAS TECH

  公开号：WO2011060332A2

  公开（公告）日：2011-05-19

  A method of treating a hyperproliferative disorder in a subject in need of such treatment, comprising administering to said subject, in combination, a treatment effective amount of: (a) a ceramide-increasing retinoid such as fenretinide or a pharmaceutically acceptable salt thereof; and (b) at least one (and in certain embodiments at least two) compounds selected from the groups consisting of (i) a non-18 carbon chain length L-threo-sphinganine(s) or pharmaceuticeutically acceptable salt thereof, (ii) glucosylceramide or glucosyl(dihydro)ceramide synthesis inhibitor(s), and (iii) sphingomyelin or dihydrosphingomyelin synthase inhibitor(s). Preferred L-threo-sphinganines are of carbon chain length 17 carbons, 19 carbons and 20 carbons. A preferred glucosylceramide or glucosyl(dihydro)ceramide synthesis inhibitor is D-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol. A preferred sphingomyelin or dihydrosphingomyelin synthesis inhibitor is D-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol. A preferred hyperproliferative disorder is brain cancers.
• Studies in the sphingolipids series—XVII
  作者：B. Majhofer-Oreščanin、M. Proštenik

  DOI：10.1016/0040-4020(61)80099-9

  日期：1961.1

  Erythro and threo-1,3-dihydroxy-2-amino-eicosane have been obtained by addition of nitroethanol to octadecanal and subsequent reduction of both erythro and threo-nitrodiols. Resolution with l-glutamic acid gave four optically active forms of the base. The d-configuration has been assigned to the +-erythro-isomer.

  通过向硝基十八醇中添加硝基乙醇，然后还原赤型和苏型硝基二醇，得到了赤型和苏型-1,3-二羟基-2-氨基二十二烷。用1-谷氨酸拆分得到碱的四种旋光形式。d-构型已分配给+-赤型异构体。