(2S,3S,4S,5R)-N-(3,4-dichlorobenzyl)-5-((cycloheptylamino)methyl)-3,4-dihydroxy-tetrahydrofuran-2-carboxamide | 1038821-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R)-N-(3,4-dichlorobenzyl)-5-((cycloheptylamino)methyl)-3,4-dihydroxy-tetrahydrofuran-2-carboxamide
• 英文别名: (2S,3S,4S,5R)-5-[(cycloheptylamino)methyl]-N-[(3,4-dichlorophenyl)methyl]-3,4-dihydroxyoxolane-2-carboxamide
• CAS: 1038821-32-7
• 化学式: C₂₀H₂₈Cl₂N₂O₄
• 分子量: 431.359
• InChiKey: FFDSKRABUMIRKW-YRXWBPOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  90.8
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(3,4-dichlorobenzyl)-2,5-anhydro-1-deoxy-1-[(tert-butoxycarbonyl)(cycloheptyl)amino]-D-mannonamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以77%的产率得到(2S,3S,4S,5R)-N-(3,4-dichlorobenzyl)-5-((cycloheptylamino)methyl)-3,4-dihydroxy-tetrahydrofuran-2-carboxamide
  参考文献：
  名称：

  Design, synthesis and trypanocidal activity of lead compounds based on inhibitors of parasite glycolysis

  摘要：

  The glycolytic pathway has been considered a potential drug target against the parasitic protozoan species of Trypanosoma and Leishmania. We report the design and the synthesis of inhibitors targeted against Trypanosoma brucei phosphofructokinase (PFK) and Leishmania mexicana pyruvate kinase (PyK). Stepwise library synthesis and inhibitor design from a rational starting point identified furanose sugar amino amides as a novel class of inhibitors for both enzymes with IC(50) values of 23 mu M and 26 mu M against PFK and PyK, respectively. Trypanocidal activity also showed potency in the low micromolar range and confirms these inhibitors as promising candidates for the development towards the design of anti-trypanosomal drugs. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.045

文献信息

• Design, synthesis and trypanocidal activity of lead compounds based on inhibitors of parasite glycolysis
  作者：Matthew W. Nowicki、Lindsay B. Tulloch、Liam Worralll、Iain W. McNae、Véronique Hannaert、Paul A.M. Michels、Linda A. Fothergill-Gilmore、Malcolm D. Walkinshaw、Nicholas J. Turner

  DOI：10.1016/j.bmc.2008.03.045

  日期：2008.5

  The glycolytic pathway has been considered a potential drug target against the parasitic protozoan species of Trypanosoma and Leishmania. We report the design and the synthesis of inhibitors targeted against Trypanosoma brucei phosphofructokinase (PFK) and Leishmania mexicana pyruvate kinase (PyK). Stepwise library synthesis and inhibitor design from a rational starting point identified furanose sugar amino amides as a novel class of inhibitors for both enzymes with IC(50) values of 23 mu M and 26 mu M against PFK and PyK, respectively. Trypanocidal activity also showed potency in the low micromolar range and confirms these inhibitors as promising candidates for the development towards the design of anti-trypanosomal drugs. (c) 2008 Elsevier Ltd. All rights reserved.