1-(3-aminopropyl)amino-1,2,5-trideoxy-2,5-imino-D-mannitol | 315190-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(3-aminopropyl)amino-1,2,5-trideoxy-2,5-imino-D-mannitol
• 英文别名: (2R,3R,4R,5R)-2-[(3-aminopropylamino)methyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol
• CAS: 315190-53-5
• 化学式: C₉H₂₁N₃O₃
• 分子量: 219.284
• InChiKey: HXUWYICAKDKCTQ-FNCVBFRFSA-N

物化性质

• 沸点：
  436.6±40.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  111
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丹酰氯 、 1-(3-aminopropyl)amino-1,2,5-trideoxy-2,5-imino-D-mannitol 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以88%的产率得到1-(N-dansylaminopropyl)amino-1,2,5-trideoxy-2,5-imino-D-mannitol
  参考文献：
  名称：

  Fine tuning of β-glucosidase inhibitory activity in the 2,5-dideoxy-2,5-imino-d-mannitol (DMDP) system

  摘要：

  Based on our extensive studies of D-glucosidase inhibiting 2,5-dideoxy-2,5-imino-D-mannitol derivatives, we have been trying to create a series of fluorescent derivatives with a view to an 'inhibitory activity ruler' based on competitive displacement reactions of non-fluorescent inhibitors by fluorescent ones and vice versa, which can be performed and followed in microtiter plates or on-chips. Thus, a set of compounds was assembled with K-i values between 2 nM and 1 mu M against Agrobacterium sp. beta-glucosidase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.010
• 作为产物：
  描述：

  5-azido-1-(N-benzyl-N-cyanoethylene)amino-1,5-dideoxy-D-fructopyranose 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以31%的产率得到1-(3-aminopropyl)amino-1,2,5-trideoxy-2,5-imino-D-mannitol
  参考文献：
  名称：

  Biologically Active 1-Aminodeoxy and 1-O-Alkyl Derivatives of The Powerful D-Glucosidase Inhibitor 2,5-Dideoxy-2,5-Imino-D-Mannitol

  摘要：

  By an Amadori rearrangement of easily available 5-azido-5-deoxy-D-glucofuranose with dibenzylamine and subsequent catalytic hydrogenation of the resulting 5-azido-1-(N,N-dibenzyl)amino-1,5-dideoxy-D-fructopyranose 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol was obtained in only two steps and in excellent overall yield. Likewise, other amines were employed to introduce extended side chains ultimately suitable for attachment of the inhibitor to solid supports. The reported rearrangement reaction is a high yielding, convenient and apparently general entry to I-amino deoxyketopyranoses modified at C-5, facilitated by the ring enlargement of the aldofuranose to the ketopyranose as an additional driving force. A range of selected chain extended analogues was prepared by acylation of N-1. Inhibitors obtained exhibit K-i-values with D-glucosidases in the micromolar range. Interestingly, 1-N-acylation resulted in superior inhibitory activities, as did the addition of a hexyl chain.

  DOI：

  10.1080/07328300008544129

文献信息

• Fine tuning of β-glucosidase inhibitory activity in the 2,5-dideoxy-2,5-imino-d-mannitol (DMDP) system
  作者：Tanja M. Wrodnigg、Arnold E. Stütz、Chris A. Tarling、Stephen G. Withers

  DOI：10.1016/j.carres.2006.03.010

  日期：2006.7

  Based on our extensive studies of D-glucosidase inhibiting 2,5-dideoxy-2,5-imino-D-mannitol derivatives, we have been trying to create a series of fluorescent derivatives with a view to an 'inhibitory activity ruler' based on competitive displacement reactions of non-fluorescent inhibitors by fluorescent ones and vice versa, which can be performed and followed in microtiter plates or on-chips. Thus, a set of compounds was assembled with K-i values between 2 nM and 1 mu M against Agrobacterium sp. beta-glucosidase. (c) 2006 Elsevier Ltd. All rights reserved.
• Biologically Active 1-Aminodeoxy and 1-<i>O</i>-Alkyl Derivatives of The Powerful D-Glucosidase Inhibitor 2,5-Dideoxy-2,5-Imino-D-Mannitol
  作者：Tanja M. Wrodnigg、Walter Gaderbauer、Peter Greimel、Herwig Häusler、Friedrich K. (Fitz) Sprenger、Arnold E. Stütz、Chris Virgona、Stephen G. Withers

  DOI：10.1080/07328300008544129

  日期：2000.1.1

  By an Amadori rearrangement of easily available 5-azido-5-deoxy-D-glucofuranose with dibenzylamine and subsequent catalytic hydrogenation of the resulting 5-azido-1-(N,N-dibenzyl)amino-1,5-dideoxy-D-fructopyranose 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol was obtained in only two steps and in excellent overall yield. Likewise, other amines were employed to introduce extended side chains ultimately suitable for attachment of the inhibitor to solid supports. The reported rearrangement reaction is a high yielding, convenient and apparently general entry to I-amino deoxyketopyranoses modified at C-5, facilitated by the ring enlargement of the aldofuranose to the ketopyranose as an additional driving force. A range of selected chain extended analogues was prepared by acylation of N-1. Inhibitors obtained exhibit K-i-values with D-glucosidases in the micromolar range. Interestingly, 1-N-acylation resulted in superior inhibitory activities, as did the addition of a hexyl chain.