2-amino-2-octadecylpropane-1,3-diol | 162359-34-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-amino-2-octadecylpropane-1,3-diol
• 英文别名: 2-amino-2-octadecyl-1,3-propanediol
• CAS: 162359-34-4
• 化学式: C₂₁H₄₅NO₂
• 分子量: 343.594
• InChiKey: QZYAIOMYEGPVPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  19
• 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

• 作为反应物：
  描述：

  乙酸酐 、 2-amino-2-octadecylpropane-1,3-diol 在 吡啶 作用下， 生成 2-acetamido-1,3-diacetoxy-2-octadecylpropane
  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：

  diethyl 2-acetamido-2-octadecylmalonate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-amino-2-octadecylpropane-1,3-diol
  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

文献信息

• Systematic synthesis of novel phosphoglycolipid analogues as potential agonists of GPR55
  作者：Junpei Abe、Adam T. Guy、Feiqing Ding、Peter Greimel、Yoshio Hirabayashi、Hiroyuki Kamiguchi、Yukishige Ito

  DOI：10.1039/d0ob01756f

  日期：——

  LPGlc analogues having the squaryldiamide group as potential agonists of GPR55. By the axon turning assay, several analogues exhibited similar activities to that of LPGlc. These results will provide valuable information for understanding the mode of action of LPGlc and its analogues and for the discovery of potent and selective antagonists or agonists of GPR55.

  视紫红质样 G 蛋白偶联受体 (GPCR) GPR55 作为药物靶标引起了人们的关注，因为它与各种生理和病理事件有关。尽管 GPR55 最初作为大麻素受体被去孤儿化，但溶血磷脂酰肌醇 (LPI) 现在被广泛认为是 GPR55 的内源性配体。最近，溶血磷脂酰-β- D已发现-葡萄糖苷 (LPGlc) 作用于 GPR55 以排斥背根神经节 (DRG) 神经元。在这项研究中，我们设计并合成了各种具有方酸二酰胺基团的 LPGlc 类似物作为 GPR55 的潜在激动剂。通过轴突转动试验，几种类似物表现出与 LPGlc 相似的活性。这些结果将为了解 LPGlc 及其类似物的作用方式以及发现 GPR55 的有效和选择性拮抗剂或激动剂提供有价值的信息。
• [EN] PHOSPHINANE COMPOUNDS WITH IMMUNOMODULATING ACTIVITY<br/>[FR] COMPOSES DE PHOSPHINANE A EFFET IMMUNOMODULATEUR
  申请人：MITSUBISHI PHARMA CORP

  公开号：WO2005014603A1

  公开（公告）日：2005-02-17

  The invention is directed to a phosphinane compound having a unique immunomodulating activity, a process for a preparation thereof, a pharmaceutical composition containing the same, and a method of preventing or treating disorders or diseases mediated by T lymphocytes by administering the compound to a subject in need of treatment.

  这项发明涉及一种具有独特免疫调节活性的膦环化合物，其制备方法，含有该化合物的药物组合物，以及通过向需要治疗的受试者施用该化合物来预防或治疗由T淋巴细胞介导的疾病或疾病的方法。
• 2-AMINO-1,3-PROPANEDIOL COMPOUND AND IMMUNOSUPPRESSANT
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0627406A1

  公开（公告）日：1994-12-07

  A 2-amino-1,3-propanediol compound represented by general formula (I) or a pharmaceutically acceptable salt thereof, and an immunosuppressant containing the same as the active ingredient. In said formula R represents optionally substituted linear or branched carbon chain, optionally substituted aryl or optionally substituted cycloalkyl; and R2, R3, R4 and R5, which may be the same or different from one another, represent each hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl. The compound is immunodepressant and useful as an inhibitor against rejection in organ or bone marrow transplantation, as a preventive or remedy for autoimmune diseases and so forth, or a reagent in the medical and pharmaceutical fields.

  一种由通式(I)代表的2-氨基-1,3-丙二醇化合物或其药学上可接受的盐，以及一种以其为活性成分的免疫抑制剂。在所述式中，R 代表任选取代的直链或支链碳链、任选取代的芳基或任选取代的环烷基；而 R2、R3、R4 和 R5（它们彼此可以相同或不同）分别代表氢、烷基、芳烷基、酰基或烷氧基羰基。该化合物具有免疫抑制作用，可作为器官移植或骨髓移植中的排斥抑制剂、自身免疫性疾病的预防或治疗药物等，也可作为医疗和制药领域的试剂。
• EP0627406B1
  申请人：——

  公开号：EP0627406B1

  公开（公告）日：1998-10-28
• COMBINED CHEMICAL MODIFICATION OF SPHINGOSINE-1-PHOSPHATE (S1P) AND CXCR4 SIGNALLING PATHWAYS FOR HEMATOPOIETIC STEM CELL (HSC) MOBILIZATION AND ENGRAFTMENT
  申请人：Children's Medical Center Corporation

  公开号：EP2720690A1

  公开（公告）日：2014-04-23