(1R)-1-C-nonyl-1,5-dideoxy-1,5-imino-D-xylitol | 929880-74-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (1R)-1-C-nonyl-1,5-dideoxy-1,5-imino-D-xylitol
• 英文别名: (1R)-1,5-dideoxy-1,5-imino-1-C-nonyl-D-xylitol；α-1-C-nonyl-iminoxylitol；(2R,3S,4S,5R)-2-nonylpiperidine-3,4,5-triol
• CAS: 929880-74-0
• 化学式: C₁₄H₂₉NO₃
• 分子量: 259.389
• InChiKey: WVYPOMDXOXCTJU-MQYQWHSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-碘丁烷 、 (1R)-1-C-nonyl-1,5-dideoxy-1,5-imino-D-xylitol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以15%的产率得到(2R,3S,4S,5R)-1-Butyl-2-nonylpiperidine-3,4,5-triol
  参考文献：
  名称：

  Novel Compounds of the Family of Iminosugars, Uses Thereof for Trewating Lysosomal Diseases, and Method for Preparing Same

  摘要：

  该发明涉及一种通式（I）中的化合物的使用，其中：R0特指氢原子或烷基基团；R1特指氢原子或烷基基团；R2、R3和R4特指，独立地，氢原子、羟基团、烷氧基或酰氧基，用于制备一种治疗至少一种溶酶体葡糖苷酶酶功能障碍相关的溶酶体疾病的药物。

  公开号：

  US20080269285A1
• 作为产物：
  描述：

  nonylmagnesium bromide 在 盐酸 、 溶剂黄146 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 140.5h， 生成 (1R)-1-C-nonyl-1,5-dideoxy-1,5-imino-D-xylitol
  参考文献：
  名称：

  Novel Compounds of the Family of Iminosugars, Uses Thereof for Trewating Lysosomal Diseases, and Method for Preparing Same

  摘要：

  该发明涉及一种通式（I）中的化合物的使用，其中：R0特指氢原子或烷基基团；R1特指氢原子或烷基基团；R2、R3和R4特指，独立地，氢原子、羟基团、烷氧基或酰氧基，用于制备一种治疗至少一种溶酶体葡糖苷酶酶功能障碍相关的溶酶体疾病的药物。

  公开号：

  US20080269285A1

文献信息

• Synthesis and Evaluation of Lipophilic Aza-C-glycosides as Inhibitors of Glucosylceramide Metabolism
  作者：Tom Wennekes、Richard J. B. H. N. van den Berg、Thomas J. Boltje、Wilma E. Donker-Koopman、Bastiaan Kuijper、Gijsbert A. van der Marel、Anneke Strijland、Carlo P. Verhagen、Johannes M. F. G. Aerts、Herman S. Overkleeft

  DOI：10.1002/ejoc.200901208

  日期：2010.3

  The structure–activity relationship of lipophilic aza-C-glycosides as inhibitors of the three enzymes of glucosylceramide metabolism is investigated. A library of β-aza-C-glycosides was synthesized with variations in N-alkylation and the linker length/type to the lipophilic moiety. A cross-metathesis reaction was used to prepare a second library of α-aza-C-glycosides with D-gluco, L-ido and D-xylo

  研究了亲脂性氮杂-C-糖苷作为葡萄糖神经酰胺代谢三种酶抑制剂的构效关系。合成了一个 β-氮杂-C-糖苷库，其中 N-烷基化和亲脂性部分的接头长度/类型有所不同。使用交叉复分解反应制备第二个 α-氮杂-C-糖苷库，其中 D-葡萄糖、L-ido 和 D-木亚氨基糖核心具有类似的接头变异。对两个文库的评估均未发现葡萄糖神经酰胺合酶的有效或选择性抑制剂。然而，发现 β-aza-C-glycoside 43 是 β-glucosidase 2 的选择性抑制剂。葡萄糖脑苷脂酶的选择性抑制剂。
• An improved methodology for the synthesis of 1-C-allyl imino-d-xylitol and -l-arabinitol and their rapid functionalization
  作者：Anna Biela、Farah Oulaïdi、Estelle Gallienne、Marcin Górecki、Jadwiga Frelek、Olivier R. Martin

  DOI：10.1016/j.tet.2012.12.082

  日期：2013.4

  As part of our research program dedicated to the design and synthesis of new iminosugars as pharmacological chaperones for the treatment of lysosomal storage disorders, we developed a rapid and efficient methodology for the access to functionalized and non-functionalized 1-C-alkylated derivatives in the d-xylo and l-arabino series. These compounds, as gluco and galacto mimics, were designed to be potent

  作为我们致力于设计和合成新的亚氨基糖作为溶酶体贮积症的药理分子伴侣的研究计划的一部分，我们开发了一种快速有效的方法，可从中获得功能化和非功能化的1- C烷基化衍生物。d - xylo和l - arabino系列。这些化合物，如葡萄糖和半乳糖模拟物，被设计成分别是与高雪氏病有关的β-葡萄糖脑苷脂酶和负责Krabbe病的β-半乳糖脑苷脂酶的有效抑制剂。合成的关键步骤是将烯丙基三甲基硅烷非对映选择性地加到d-低聚木糖或升-阿拉伯ñ -苄氧保护glycopyranosylamine。该保护基允许使用复分解或氧化反应将获得的亚氨基糖直接官能化。为了确定二羟基化反应产物的绝对构型，成功地使用了电子圆二色性光谱法的原位二钼法。
• 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.
• Novel Compounds of the Family of Iminosugars, Uses Thereof for Trewating Lysosomal Diseases, and Method for Preparing Same
  申请人：Martin Olivier Richard

  公开号：US20080269285A1

  公开（公告）日：2008-10-30

  The invention concerns the use of a compound of general formula (I) wherein: R 0 represents in particular a hydrogen atom or an alkyl group; R 1 represents in particular a hydrogen atom or an alkyl group; R 2 , R 3 and R 4 represent in particular, independently of one another, a hydrogen atom, a hydroxyl group, an alkoxy group or an acyloxy group, for preparing a medicine for treating lysosomal diseases related to a dysfunction of at least one lysosomal glycosidase enzyme.

  该发明涉及一种通式（I）中的化合物的使用，其中：R0特指氢原子或烷基基团；R1特指氢原子或烷基基团；R2、R3和R4特指，独立地，氢原子、羟基团、烷氧基或酰氧基，用于制备一种治疗至少一种溶酶体葡糖苷酶酶功能障碍相关的溶酶体疾病的药物。