(1S,2S,3S,5S,8aR)-3-(hydroxymethyl)-5-[(4-methoxyphenyl)methyl]-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2-diol | 1346678-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S,2S,3S,5S,8aR)-3-(hydroxymethyl)-5-[(4-methoxyphenyl)methyl]-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2-diol
• CAS: 1346678-95-2
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: BBFIZQSHNUXXOW-OBCVZTRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  73.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 盐酸 、 palladium 10% on activated carbon 、 水 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以57%的产率得到(1S,2S,3S,5S,8aR)-3-(hydroxymethyl)-5-[(4-methoxyphenyl)methyl]-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2-diol
  参考文献：
  名称：

  An expeditious synthesis of an analogue of (−)-steviamine by way of the 1,3-dipolar cycloaddition of a nitrile oxide with a 1-C-allyl iminosugar

  摘要：

  In our continuing effort to develop inhibitors of the mycobacterial galactan biosynthesis, we planned to synthesize original iminosugar-based analogues of UDP-galactofuranose by way of the 1,3-dipolar cycloaddition reaction between a 1-C-allyl iminosugar and a nitrile oxide, followed by the reductive cleavage of the resulting isooxazoline. In initial studies, it was found that this last step led in one pot to a new poly-hydroxylated indolizidine derivative closely related to the recently isolated (-)-steviamine, in good yield, by way of a sequence involving at least five individual reactions. The activity of this new compound as a glycosidase inhibitor was evaluated against a panel of glycosidases and compared to (-)-steviamine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.065

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.