α-1-C-octyl-1-deoxynojirimycin | 74795-45-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: α-1-C-octyl-1-deoxynojirimycin
• 英文别名: (2R,3R,4R,5S,6R)-2-(hydroxymethyl)-6-octylpiperidine-3,4,5-triol
• CAS: 74795-45-2
• 化学式: C₁₄H₂₉NO₄
• 分子量: 275.389
• InChiKey: IIHXPVAHXKBRBL-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 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：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  正辛基镁溴盐 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 108.0h， 生成 α-1-C-octyl-1-deoxynojirimycin
  参考文献：
  名称：

  α-1-C-Alkyl-1-deoxynojirimycin derivatives as potent and selective inhibitors of intestinal isomaltase: remarkable effect of the alkyl chain length on glycosidase inhibitory profile

  摘要：

  A series of alpha- and beta-1-C-alkyl-1-deoxynojirimycin derivatives was prepared and evaluated as glycosidase inhibitors. Biological assays showed a marked dependence of the selectivity and potency of the inhibitors upon the position of the alkyl chain (alpha-1-C-, beta-1-C- or N-alkyl derivatives). In addition, the efficiency of alpha-1-C-alkyl-1-deoxynojirimycin derivatives as intestinal isomaltase inhibitors increases with the length of the alkyl chain. The strongest inhibition was found for alpha-1-C-nonyl-1-deoxynojirimycin with an IC50 = 3.5 nM (25x more potent inhibitor than the shorter chain homologue carrying a C-8 chain). These results demonstrate that subtle changes in the aglycon fragment may result in remarkable enzyme specificity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.086

文献信息

• Synthesis of the Purported Structure of Glyphaeaside C and Proposed Revisions to the Structures of the Glyphaeaside Alkaloids
  作者：Brendan J. Byatt、Atsushi Kato、Stephen G. Pyne

  DOI：10.1021/acs.jnatprod.3c00046

  日期：2023.5.26

  glyphaeaside alkaloids isolated from the roots of Glyphaea brevis were originally purported as piperidine-based 1-C-alkylated iminosugars, with the A-, B-, and C-type glyphaeasides bearing l-DFJ, DGJ, and DNJ ring configurations, respectively. Subsequent investigations have revealed glyphaeaside C as being a pyrrolidine-based iminosugar with a DMDP ring configuration via total synthesis of the revised

  从Glyphaea brevis的根中分离出的 10 种 glyphaeaside 生物碱最初被认为是基于哌啶的 1- C-烷基化亚氨基糖，其中 A-、B-和 C-型 glyphaeasides 带有l -DFJ、DGJ 和 DNJ 环构型，分别。随后的研究表明，通过全合成修改后的结构，glyphaeaside C 是一种基于吡咯烷的亚氨基糖，具有 DMDP 环构型。在这项工作中，最初提出的 glyphaeaside C ( 10 )结构的侧链非对映异构体和两种相关的 α-1- C - 烷基化 DNJ 衍生物是从共同的前体合成的，该前体依次通过立体选择性格氏加成到受保护的d上来制备。-糖胺，然后是还原胺化-环化序列。糖苷酶抑制活性研究表明，一般结构10对各种 α-葡萄糖苷酶具有强效抑制作用，对杏仁 β-葡萄糖苷酶具有弱抑制作用，与​​类似的基于 DNJ 的亚氨基糖一致，与天然 glyphaeaside
• Boeshagen; Geiger; Junge, Angewandte Chemie, 1981, vol. 93, # 9, p. 800 - 801
  作者：Boeshagen、Geiger、Junge

  DOI：——

  日期：——
• α-1-C-Alkyl-1-deoxynojirimycin derivatives as potent and selective inhibitors of intestinal isomaltase: remarkable effect of the alkyl chain length on glycosidase inhibitory profile
  作者：Guillaume Godin、Philippe Compain、Olivier R. Martin、Kyoko Ikeda、Liang Yu、Naoki Asano

  DOI：10.1016/j.bmcl.2004.09.086

  日期：2004.12

  A series of alpha- and beta-1-C-alkyl-1-deoxynojirimycin derivatives was prepared and evaluated as glycosidase inhibitors. Biological assays showed a marked dependence of the selectivity and potency of the inhibitors upon the position of the alkyl chain (alpha-1-C-, beta-1-C- or N-alkyl derivatives). In addition, the efficiency of alpha-1-C-alkyl-1-deoxynojirimycin derivatives as intestinal isomaltase inhibitors increases with the length of the alkyl chain. The strongest inhibition was found for alpha-1-C-nonyl-1-deoxynojirimycin with an IC50 = 3.5 nM (25x more potent inhibitor than the shorter chain homologue carrying a C-8 chain). These results demonstrate that subtle changes in the aglycon fragment may result in remarkable enzyme specificity. (C) 2004 Elsevier Ltd. All rights reserved.