1,5-(4,4,4-Trifluorobutylimino)-1,5-dideoxy-D-glucitol | 128985-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,5-(4,4,4-Trifluorobutylimino)-1,5-dideoxy-D-glucitol
• 英文别名: 3,4,5-Piperidinetriol, 2-(hydroxymethyl)-1-(4,4,4-trifluorobutyl)-, (2R,3R,4R,5S)-；(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(4,4,4-trifluorobutyl)piperidine-3,4,5-triol
• CAS: 128985-16-0
• 化学式: C₁₀H₁₈F₃NO₄
• 分子量: 273.252
• InChiKey: YPBJLHXXZZNYIP-BZNPZCIMSA-N

物化性质

• 沸点：
  385.2±42.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-脱氧野尻霉素 、 1-溴-4,4,4-三氟丁烷 在 potassium carbonate 作用下， 以 N-甲基乙酰胺 为溶剂， 生成 1,5-(4,4,4-Trifluorobutylimino)-1,5-dideoxy-D-glucitol
  参考文献：
  名称：

  1,5-dideoxy-1,5-imino-D-glucitol derivatives

  摘要：

  披露了1,5-二去氧-1,5-亚胺-D-葡萄糖醇的O-酰化衍生物，其中含有一个到四个自由羟基被选自以下羧基烷酰基的羧基烷酰基的N-烷基或N-芳酰基，.omega.，.omega.，.omega.-三氟烷酰基，碳原子数为三至八个，具有四至八个碳原子的羧基环烷酰基和具有两至十个碳原子的羧基无环烷酰基，其中N-芳酰基选自以下羧基苯基，3-(对氯苯氧基)丙酰基，2-(乙酰氧基)苯甲酰基，[1,1'-联苯]-4-基甲酰基，2-噻吩乙酰基，反式-3-呋喃丙烯基3-甲氧基苯乙酰基和3-(三氟甲基)苯甲酰基，其中N-烷基含有一个到十四个碳原子，前提是当N-烷基含有一个到五个碳原子时，O-酰化基团为.omega.，.omega.，.omega.-三氟烷酰基或羧基环烷酰基。

  公开号：

  US05221746A1

文献信息

• Antiviral compounds
  申请人：G. D. Searle & Co.

  公开号：US05310745A1

  公开（公告）日：1994-05-10

  A method of inhibiting lentivirus is disclosed which comprises mammalian host susceptible to said lentivirus with a virally inhibitory effective amount of an O-acylated derivative of 1,5-dideoxy-1,5-imino-D-glucitol and their N-alkyl, N-acyl and N-aroyl derivatives in which from one to four of the free hydroxyl groups are O-acylated with carboxylic alkanoyl radicals selected from the group consisting of .omega.,.omega.,.omega.-trifluoroalkanoyl having from three to eight carbon atoms, carboxylic cycloalkanoyl groups having from four to eight carbon atoms and carboxylic acyclic alkanoyl groups having from two to ten carbon atoms, wherein the N-aroyl groups contain from 7 to 14 carbon atoms, the N-acyl groups contain from 4 to 8 carbon atoms and the N-alkyl groups contain from 1 to 14 carbon atoms.

  本发明揭示了一种抑制慢病毒的方法，包括将哺乳动物宿主暴露于所述慢病毒的有效抑制量的1,5-二去氧-1,5-亚胺-D-葡萄糖醇的O-酰化衍生物及其N-烷基，N-酰基和N-芳酰衍生物中，其中从一个到四个自由羟基被选自由三至八个碳原子的羧基烷酰基的.omega.，.omega.，.omega.-三氟烷酰基，含有四至八个碳原子的环烷基羧基和含有两至十个碳原子的无环烷基羧基，其中N-芳酰基含有七至十四个碳原子，N-酰基含有四至八个碳原子，N-烷基含有一至十四个碳原子。
• 1,5-dideoxy-1,5-imino-d-glucitol derivatives
  申请人：G. D. Searle & Co.

  公开号：US05144037A1

  公开（公告）日：1992-09-01

  Antiviral O-acylated derivatives of 1,5-dideoxy-1,5-imino-D-glucitol are disclosed that contain an N-alkyl or N-aroyl radical in which from one to four of the free hydroxyl groups are O-acylated with carboxylic alkanoyl radicals selected from the group consisting of .omega.,.omega.,.omega.-trifluoro alkanoyl having from three to eight carbon atoms, carboxylic cycloalkanoyl groups having from four to eight carbon atoms and carboxylic acyclic alkanoyl groups having from two to ten carbon atoms, wherein the N-aroyl radical is selected from the group consisting of p-decylbenzoyl, 3-(p-chlorophenoxy)propanoyl, 2-(acetyloxy)benzoyl, [1,1'-biphenyl]-4-ylcarbonyl, 2-thiopheneacetyl, trans-3-furanacryloyl, 3-methoxyphenylacetyl and 3-(trifluoromethyl)benzoyl, and wherein the N-alkyl contains from one to fourteen carbon atoms, provided that when N-alkyl contains from one to five carbon atoms the O-acylated groups are .omega.,.omega.,.omega.-trifluoro alkanoyl or carboxylic cycloalkanoyl.

  本发明涉及1,5-二去氧-1,5-亚硝基-D-葡萄糖醇的抗病毒O-酰化衍生物，其中含有一个至四个游离羟基被选自由从三到八个碳原子的羧基脂肪酰基所选择的ω,ω,ω-三氟代烷酰基、从四到八个碳原子的环烷基羧基和从二到十个碳原子的非环烷基羧基的N-烷基或N-芳酰基，其中N-芳酰基被选自p-癸基苯甲酰基、3-(对氯苯氧基)丙酰基、2-(乙酰氧基)苯甲酰基、[1,1'-联苯]-4-基羰基、2-噻吩乙酰基、反式-3-呋喃丙烯酰基、3-甲氧基苯乙酰基和3-(三氟甲基)苯甲酰基，其中N-烷基含有从一个到十四个碳原子，但当N-烷基含有从一个到五个碳原子时，O-酰化基为ω,ω,ω-三氟代烷酰基或环烷基羧基。
• Glucamine salts for treating hepatitis virus infections
  申请人：Pharmacia Corporation

  公开号：US20030195229A1

  公开（公告）日：2003-10-16

  N-Substituted glucamine compounds of Formula I are effective in treatment of hepatitis infections, including hepatitis B and hepatitis C. In treating hepatitis infections, the compounds of Formula I may be used alone, or in combination with another antiviral agent selected from among nucleosides, nucleotides, immunomodulators, immunostimulants or various combinations of such other agents.

  式I的N-取代葡萄糖胺化合物在治疗肝炎感染，包括乙型肝炎和丙型肝炎方面具有有效性。在治疗肝炎感染时，式I的化合物可以单独使用，也可以与从核苷，核苷酸，免疫调节剂，免疫刺激剂或各种这些其他剂量中选择的另一种抗病毒剂联合使用。
• Novel antiviral compounds
  申请人：G.D. Searle & Co.

  公开号：EP0494850A2

  公开（公告）日：1992-07-15

  O-acylated derivatives of 1,5-dideoxy-1,5-imino-D-glucitol are disclosed that contain an N-alkyl or N-aroyl radical in which from one to four of the free hydroxyl groups are O-acylated with carboxylic alkanoyl radicals selected from the group consisting of w,w,w-trifluoro alkanoyl having from three to eight carbon atoms, carboxylic cycloalkanoyl groups having from four to eight carbon atoms and carboxylic acyclic alkanoyl groups having from two to ten carbon atoms, wherein the N-aroyl radical is selected from the group consisting of p-decylbenzoyl, 3-(p-chlorophenoxy)-propanoyl, 2-(acetyloxy)benzoyl, [1,1' -biphenyl]-4-ylcarbonyl, 2-thiopheneacetyl, trans-3-furanacryloyl, 3-methoxyphenylacetyl and 3-(trifluoromethyl)benzoyl, and wherein the N-alkyl contains from one to fourteen carbon atoms, provided that when N-alkyl contains from one to five carbon atoms the O-acylated groups are w,w,w-trifluoro alkanoyl or carboxylic cycloalkanoyl.

  本发明公开了 1,5-二脱氧-1,5-亚氨基-D-葡萄糖醇的 O-酰化衍生物，该衍生物含有 N-烷基或 N-芳酰基，其中 1 至 4 个游离羟基与选自以下组别的羧基烷酰基 O-酰化：具有 3 至 8 个碳原子的 w,w-三氟烷酰基、具有 4 至 8 个碳原子的羧基环烷酰基和羧基无环烷酰基、w，w-三氟烷氧基（具有 3 至 8 个碳原子）、环烷氧基（具有 4 至 8 个碳原子）和无环烷氧基（具有 2 至 10 个碳原子）组成的组、其中，N-芳酰基选自由对-癸基苯甲酰基、3-（对氯苯氧基）-丙酰基、2-（乙酰氧基）苯甲酰基、[1,1'-联苯]-4-基羰基、2-噻吩乙酰基、反式-3-呋喃丙烯酰基、3-甲氧基苯乙酰基和 3-（三氟甲基）苯甲酰基组成的组、其中 N-烷基含有 1 至 14 个碳原子，但当 N-烷基含有 1 至 5 个碳原子时，O-酰化基团为 w,w,w-三氟烷酰基或羧基环烷酰基。
• Substituted-1,5-dideoxy-1,5-imino-D-glucitol compounds for treating hepatitis virus infections
  申请人：G.D. Searle & Co.

  公开号：EP1658846A1

  公开（公告）日：2006-05-24

  N-Substituted-1,5-dideoxy-1,5-imino-D-glucitol compounds of Formula (I) are effective in treatment of hepatitis infections, including hepatitis B and hepatitis C. In treating hepatitis infections, the compounds of Formula (I) may be used alone, or in combination with another antiviral agent selected from among nucleosides, nucleotides, immunomodulators, immunostimulants or various combinations of such other agents.

  N-取代的-1,5-二脱氧-1,5-亚氨基-D-葡萄糖醇式（I）化合物可有效治疗肝炎感染，包括乙型肝炎和丙型肝炎。在治疗肝炎感染时，式（I）化合物可单独使用，也可与选自核苷类、核苷酸类、免疫调节剂、免疫刺激剂或此类其它药物的各种组合中的另一种抗病毒剂联合使用。