N-[[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]methyl]-5-(dimethylamino)naphthalene-1-sulfonamide | 351351-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]methyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 351351-86-5
• 化学式: C₁₈H₂₅N₃O₅S
• 分子量: 395.48
• InChiKey: YQDDYECBODRLCI-DTTOXWODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  131
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]methyl]-5-(dimethylamino)naphthalene-1-sulfonamide 在 sodium hydroxide 、 sodium cyanoborohydride 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 36.0h， 生成 1-N-dansyl-2-N-(methoxycarbonylpentyl)aminocarbonylpentyl-1-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：

  丹酰氯 、 3,4-吡咯烷二醇,2-(氨基甲基)-5-(羟甲基)-,(2R,3R,4R,5R)- 以 甲醇 、 乙腈 为溶剂， 以40%的产率得到N-[[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]methyl]-5-(dimethylamino)naphthalene-1-sulfonamide
  参考文献：
  名称：

  Powerful probes for glycosidases

  摘要：

  1-Amino-1,2,5-trideoxy-2,5-imino-D-mannitol was fluorescently tagged by reaction with dansyl chloride at N-1 or by attachment of a dansyl amide bearing spacer to this centre. Compounds obtained are highly potent inhibitors of beta -glucosidase exhibiting K-i values in the single figure nanosmolar range. The 1-N-dansyl substituted inhibitor was successfully exploited for binding studies with beta -glucosidase from Agrobacterium sp. employing fluorescence spectrometric methods. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00209-8

文献信息

• Powerful probes for glycosidases
  作者：Albin Hermetter、Hubert Scholze、Arnold E. Stütz、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/s0960-894x(01)00209-8

  日期：2001.5

  1-Amino-1,2,5-trideoxy-2,5-imino-D-mannitol was fluorescently tagged by reaction with dansyl chloride at N-1 or by attachment of a dansyl amide bearing spacer to this centre. Compounds obtained are highly potent inhibitors of beta -glucosidase exhibiting K-i values in the single figure nanosmolar range. The 1-N-dansyl substituted inhibitor was successfully exploited for binding studies with beta -glucosidase from Agrobacterium sp. employing fluorescence spectrometric methods. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.