N-(2-aminoethyl)-2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol | 205649-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-aminoethyl)-2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
• 英文别名: 2-((2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)piperidin-1-yl)ethan-1-amine；2-[(2R,3R,4R,5S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)piperidin-1-yl]ethanamine
• CAS: 205649-40-7
• 化学式: C₃₆H₄₂N₂O₄
• 分子量: 566.74
• InChiKey: WVDKJERZBGUEGZ-IYKITFJXSA-N

物化性质

• 沸点：
  669.8±55.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.18
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(2-aminoethyl)-2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 50.5h， 生成 N-<2-<<1R-(1α,2β,3α,4β,5β)>-<1-(tert-butyldimethylsilyloxymethyl)-1-hydroxy-2,3,4-tris(tert-bityldimethylsilyloxy)cyclopent-5-yl>aminothiocarbonyl>aminoethyl>-2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  Synthesis of 1-deoxynojirimycin-trehalamine fused compound and its related compounds

  摘要：

  1-Deoxynojirimycin-trehalamine fused compound 10 as a mixture together with 11 and its related compound 19 were synthesized The enzyme inhibitory activities of the mixture (10 and 11), 19 and 20 exhibited IC50 values of 0.68, 4.2, and 1.5 mu g/ml, respectively, toward rat intestinal maltase. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00049-5
• 作为产物：
  描述：

  N--2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 在 硼烷四氢呋喃络合物 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 N-(2-aminoethyl)-2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  Synthesis of 1-deoxynojirimycin-trehalamine fused compound and its related compounds

  摘要：

  1-Deoxynojirimycin-trehalamine fused compound 10 as a mixture together with 11 and its related compound 19 were synthesized The enzyme inhibitory activities of the mixture (10 and 11), 19 and 20 exhibited IC50 values of 0.68, 4.2, and 1.5 mu g/ml, respectively, toward rat intestinal maltase. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00049-5

文献信息

• Study on the Synthesis and Biological Activities of N-Alkylated Deoxynojirimycin Derivatives with a Terminal Tertiary Amine
  作者：Lin Wang、Zhijie Fang

  DOI：10.17344/acsi.2019.5778

  日期：——

  derivatives connected to a terminal tertiary amine at the alkyl chains of various lengths were prepared. These novel synthetic compounds were assessed for preliminary glucosidase inhibition and anticancer activities in vitro . Potent and selective inhibition was observed among them. Compound 7d (IC 50 = 0.052 mM) showed improved and selective inhibitory activity against β-glucosidase compared to DNJ

  制备了一系列在各种长度的烷基链上连接至末端叔胺的N-烷基化脱氧野oji霉素（DNJ）衍生物。这些新的合成化合物进行了初步的葡萄糖苷酶抑制和抗癌活性的体外评价。其中观察到有效和选择性抑制。与DNJ（IC 50 = 0.65 mM）相比，化合物7d（IC 50 = 0.052 mM）对β-葡萄糖苷酶表现出改善的选择性抑制活性。此外，使用Lineweaver-Burk图对酶抑制动力学进行分析，结果表明7d以竞争方式抑制了β-葡萄糖苷酶，这表明7d有望与β-葡萄糖苷酶的活性位点结合。发现化合物8b和8c是α-葡萄糖苷酶的中度和选择性抑制剂。尽管如此，
• Syntheses of 1-deoxynojirimycin-trehalamine-fused and -linked compounds and their biological activities
  作者：Masao Shiozaki、Reiko Yoshiike、Osamu Ando、Osamu Ubukata、Hideyuki Haruyama

  DOI：10.1016/s0040-4020(98)00966-1

  日期：1998.12

  1-Deoxynojirimycin-trehalamine-fused and -linked compounds (10, 19a and 19b) were synthesized from 1-deoxy-2,3,4,6-tetra-O-benzylnojirimycin and trehazolamine, which was obtained from natural trehazorin as a degradation product. None of these synthetic compounds exceeded 1-deoxynojirimycin in the inhibitory activities towards rat intestinal maltase and yeast alpha-D-glucosidase. (C) 1998 Elsevier Science Ltd. All rights reserved.