(3R,5R)-二羟基哌啶 | 1043449-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (3R,5R)-二羟基哌啶
• 英文名称: (3R,5R)-piperidine-3,5-diol
• 英文别名: (3R,5R)-dihydroxypiperidine；3,5-dihydroxypiperidine；(3R,5R)-3,5-dihydroxypiperidine
• CAS: 1043449-04-2
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: QCQKTGJRAPFKRX-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5R)-二羟基哌啶 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 10% palladium on activated charcoal 、 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 (3S,5R)-3-amino-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidine
  参考文献：
  名称：

  The synthesis of piperidine nucleoside analogs—a comparison of several methods to access the introduction of nucleobases

  摘要：

  This work deals with the synthesis of piperidine and hydroxypiperidine analogs of nucleosides. Starting from commercially available 3-hydroxypiperidine, proline or 4-hydroxyproline, a series of piperidine derivatives of both purine and pyrimidine nucleobases was prepared. Various methods of nucleobase attachment were evaluated. The prepared compounds were tested for cytostatic, antibacterial, and antiviral properties but no significant activity was found. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.029
• 作为产物：
  描述：

  (2S,4R)-1-benzyl-4-hydroxyproline methyl ester 在 lithium aluminium tetrahydride 、 10% palladium on activated charcoal 、 氢气 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 141.66h， 生成 (3R,5R)-二羟基哌啶
  参考文献：
  名称：

  The synthesis of piperidine nucleoside analogs—a comparison of several methods to access the introduction of nucleobases

  摘要：

  This work deals with the synthesis of piperidine and hydroxypiperidine analogs of nucleosides. Starting from commercially available 3-hydroxypiperidine, proline or 4-hydroxyproline, a series of piperidine derivatives of both purine and pyrimidine nucleobases was prepared. Various methods of nucleobase attachment were evaluated. The prepared compounds were tested for cytostatic, antibacterial, and antiviral properties but no significant activity was found. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.029

文献信息

• [EN] PYRROLO[3,2] PYRIMIDINE DERIVATIVES AS INDUCERS OF HUMAN INTERFERON<br/>[FR] DÉRIVÉS DE PYRROLO[3,2]PYRIMIDINE EN TANT QU'INDUCTEURS D'INTERFÉRON HUMAIN
  申请人：GLAXOSMITHKLINE IP NO 2 LTD

  公开号：WO2015124591A1

  公开（公告）日：2015-08-27

  Compounds of formula (I) and salts thereof: (I) wherein R1 is hydrogen, methyl or –(CH2 )2 OR3, R2 is methyl or –(CH2)2 OR4, or R1 and R2, together with the nitrogen atom to which they are attached, are linked to form a 5-or 6- membered heterocyclyl wherein the 6-membered heterocyclyl is optionally substituted by two hydroxy substituents; R3 and R4 are each independently hydrogen or methyl; and n is an integer having a value of 5 or 6, are inducers of human interferon. Compounds which induce human interferon may be useful in the treatment or prevention of various disorders, for example the treatment or prevention of allergic diseases and other inflammatory conditions, for example allergic rhinitis and asthma, infectious diseases and cancer, and may also be useful as vaccine adjuvants.

  式（I）的化合物及其盐：其中R1为氢、甲基或-(CH2)2OR3，R2为甲基或-(CH2)2OR4，或者R1和R2与它们连接的氮原子一起形成5-或6-成员杂环基，其中6-成员杂环基可选择地被两个羟基取代；R3和R4各自独立地为氢或甲基；n为取值为5或6的整数，是人类干扰素的诱导剂。诱导人类干扰素的化合物可能在治疗或预防各种疾病方面有用，例如治疗或预防过敏性疾病和其他炎症性疾病，例如过敏性鼻炎和哮喘，传染病和癌症，也可能作为疫苗佐剂有用。
• Lipophosphonoxins, method of their preparation and use
  申请人：Ustav organicke chemie a biochemie AV CR, v.v.i.

  公开号：EP2527351B1

  公开（公告）日：2013-12-11
• Lipophosphonoxins: New Modular Molecular Structures with Significant Antibacterial Properties
  作者：Dominik Rejman、Alžbeta Rabatinová、António R. Pombinho、Soňa Kovačková、Radek Pohl、Eva Zbornı́ková、Milan Kolář、Kateřina Bogdanová、Otakar Nyč、Hana Šanderová、Tomáš Látal、Petr Bartůněk、Libor Krásný

  DOI：10.1021/jm2009343

  日期：2011.11.24

  Novel compounds termed lipophosphonoxins were prepared using a simple and efficient synthetic approach. The general structure of lipophosphonoxins consists of four modules: (i) a nucleoside module, (ii) an iminosugar module, (iii) a hydrophobic module (lipophilic alkyl chain), and (iv) a phosphonate linker module that holds together modules i-iii. Lipophosphonoxins displayed significant antibacterial properties against a panel of Gram-positive species, including multiresistant strains. The minimum inhibitory concentration (MIC) values of the best inhibitors were in the 1-12 mu g/mL range, while their cytotoxic concentrations against human cell lines were significantly above this range. The modular nature of this artificial scaffold offers a large number of possibilities for further modifications/exploitation of these compounds.
• The synthesis of piperidine nucleoside analogs—a comparison of several methods to access the introduction of nucleobases
  作者：Soňa Kovačková、Martin Dračínský、Dominik Rejman

  DOI：10.1016/j.tet.2010.12.029

  日期：2011.2

  This work deals with the synthesis of piperidine and hydroxypiperidine analogs of nucleosides. Starting from commercially available 3-hydroxypiperidine, proline or 4-hydroxyproline, a series of piperidine derivatives of both purine and pyrimidine nucleobases was prepared. Various methods of nucleobase attachment were evaluated. The prepared compounds were tested for cytostatic, antibacterial, and antiviral properties but no significant activity was found. (C) 2010 Elsevier Ltd. All rights reserved.