β-1-C-butyl-1,5-dideoxy-1,5-imino-L-iditol | 1228359-12-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: β-1-C-butyl-1,5-dideoxy-1,5-imino-L-iditol
• 英文别名: (2S,3S,4R,5R,6S)-2-butyl-6-(hydroxymethyl)piperidine-3,4,5-triol；(2R,3S,4R,5R,6S)-2-butyl-6-(hydroxymethyl)piperidine-3,4,5-triol
• CAS: 1228359-12-3
• 化学式: C₁₀H₂₁NO₄
• 分子量: 219.281
• InChiKey: ZSNFEMNRWFDMNU-SOYHJAILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 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：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-benzyl-2,3,4,6-tetra-O-benzyl-β-1-C-butyl-1,5-dideoxy-1,5-imino-L-iditol 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 钯 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 以76%的产率得到β-1-C-butyl-1,5-dideoxy-1,5-imino-L-iditol
  参考文献：
  名称：

  Synthesis of new β-1-C-alkylated imino-l-iditols: A comparative study of their activity as β-glucocerebrosidase inhibitors

  摘要：

  A short synthesis of new beta-1-C-alkyl-1,5-dideoxy-1,5-imino-L-iditols by means of the diastereoselective addition of Grignard reagents onto a glucopyranosylamine is described. These compounds were evaluated as beta-glucocerebrosidase inhibitors and their activity was compared with that of related iminosugar derivatives in the D-gluco and D-xylo series. The results allowed us to conclude on the influence of the hydroxymethyl moiety and of the piperidine-ring conformation on the inhibitory activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.027

文献信息

• Compounds for their use as drugs for the treatment and/or the prevention of infection(s) caused by biofilm-forming bacteria
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US10745395B2

  公开（公告）日：2020-08-18

  The present invention relates to compounds of the following formula (I), wherein: m represents an integer being equal to 0, 1, 2, 3, 4, 5 or 6, X represents a simple bond or a radical —CHR1 wherein R1 represents:—a hydrogen atom, or—a linear or branched, possibly interrupted by up to 3 heteroatoms selected from O, S or N and/or possibly substituted, (C1-C12)-alkyl, R2, R3 and R4 represent independently from each other:—a hydrogen atom, or—a linear or branched (C1-C12-alkyl or (C1-C12)-acyl R5 represents:—a hydrogen atom, or—a linear or branched, possibly substituted, (C1-C13)-alkyi possibly substituted and possibly interrupted by up to 3 heteroatoms selected from O, S or N, R6 represents:—a hydrogen atom, or—a linear or branched possibly substituted (C1-C12)-alkyl, possibly substituted and possibly interrupted by up to 3 heteroatoms selected from O, S or N, for their use as antibacterial drugs for the treatment and/or the prevention of infection(s) caused by biofilm-forming bacteria.

  本发明涉及下式（I）的化合物，其中：m 代表等于 0、1、2、3、4、5 或 6 的整数，X 代表单键或自由基-CHR1，其中 R1 代表：氢原子，或直链或支链的、可能被最多 3 个选自 O、S 或 N 的杂原子间断的和/或可能被取代的 (C1-C12)- 烷基，R2、R3 和 R4 相互独立地代表：氢原子，或直链或支链的 (C1-C12) - 烷基或 (C1-C12)- 芳基 R5 代表：氢原子，或直链或支链的 (C1-C12)- 烷基或 (C1-C12)- 芳基-氢原子，或直链或支链、可能被取代的（C1-C13）烷基，可能被最多 3 个选自 O、S 或 N 的杂原子取代和间断，R6 代表：氢原子，或直链或支链、可能被取代的（C1-C12）烷基，可能被最多 3 个选自 O、S 或 N 的杂原子取代和间断，用作抗菌药物，用于治疗和/或预防由生物膜形成细菌引起的感染。
• COMPOUNDS FOR THEIR USE AS DRUGS FOR THE TREATMENT AND/OR THE PREVENTION OF INFECTION(S) CAUSED BY BIOFILM-FORMING BACTERIA
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20180030047A1

  公开（公告）日：2018-02-01

  Disclosed are compounds of the following formula I: wherein: m represents an integer being equal to 0, 1, 2, 3, 4, 5 or 6, X represents a simple bond or a radical —CHR 1 — wherein R 1 represents: a hydrogen atom, or a linear or branched, possibly interrupted by up to 3 heteroatoms selected from O, S or N and/or possibly substituted, (C 1 -C 12 )-alkyl, R 2 , R 3 and R 4 represent independently from each other: a hydrogen atom, or a linear or branched (C 1 -C 12 )-alkyl or (C 1 -C 12 )-acyl R 5 represents: a hydrogen atom, or a linear or branched, possibly substituted, (C 1 -C 13 )-alkyl possibly interrupted by up to 3 heteroatoms selected from O, S or N, R 6 represents: a hydrogen atom, or a linear or branched possibly substituted (C 1 -C 12 )-alkyl, possibly substituted and possibly interrupted by up to 3 heteroatoms selected from O, S or N, for their use as antibacterial drugs.
• Synthesis of new β-1-C-alkylated imino-l-iditols: A comparative study of their activity as β-glucocerebrosidase inhibitors
  作者：Wojciech Schönemann、Estelle Gallienne、Philippe Compain、Kyoko Ikeda、Naoki Asano、Olivier R. Martin

  DOI：10.1016/j.bmc.2010.02.027

  日期：2010.4

  A short synthesis of new beta-1-C-alkyl-1,5-dideoxy-1,5-imino-L-iditols by means of the diastereoselective addition of Grignard reagents onto a glucopyranosylamine is described. These compounds were evaluated as beta-glucocerebrosidase inhibitors and their activity was compared with that of related iminosugar derivatives in the D-gluco and D-xylo series. The results allowed us to conclude on the influence of the hydroxymethyl moiety and of the piperidine-ring conformation on the inhibitory activity. (C) 2010 Elsevier Ltd. All rights reserved.