N-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-N'-(2,2-dimethoxyethyl) thiourea | 362594-93-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-N'-(2,2-dimethoxyethyl) thiourea
• 英文别名: [(2R)-2-benzoyloxy-2-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-(2,2-dimethoxyethylcarbamothioylamino)oxolan-2-yl]ethyl] benzoate
• CAS: 362594-93-2
• 化学式: C₃₉H₃₈N₂O₁₁S
• 分子量: 742.804
• InChiKey: PGIGWFMGSRPRDQ-SSWJQGRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  189
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-N'-(2,2-dimethoxyethyl) thiourea 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以79%的产率得到[(2R)-2-benzoyloxy-2-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-(2-sulfanylidene-1H-imidazol-3-yl)oxolan-2-yl]ethyl] benzoate
  参考文献：
  名称：

  Synthesis of β-d-galactofuranosyl nucleoside analogues. A new type of β-d-galactofuranosidase inhibitor

  摘要：

  The development of beta -D-galactofuranosidase inhibitors provides a good chemotherapeutic target for treatment of major human diseases, because beta -D-galactofuranose is a constituent of important pathogen microorganisms but is absent in mammals. With this purpose we have prepared beta -D-galactofuranosyl nucleoside analogues, derived by the addition of nucleophiles to perbenzoylated beta -D-galactofuranosyl isothiocyanate, a compound previously prepared in this laboratory. N-beta -D-Galactofuratlosyl-O-ethylthiourethane N-beta -D-galactofuranosyl-4-oxoimidazolidi N-beta -D-galactofuranosyl-4-imidazoline-2-thione, and N-beta -D-galactofuranosyl-4-methoxyimidazolidine-2-thione, were prepared. The biological assays showed that imidazoline and imidazolidine-2-thione derivatives act as a new type of exo beta -D-galactofuranosidase inhibitor. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00146-x
• 作为产物：
  描述：

  氨基乙醛缩二甲醇 、 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl isothiocyanate 以 甲苯 为溶剂， 以92%的产率得到N-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-N'-(2,2-dimethoxyethyl) thiourea
  参考文献：
  名称：

  Synthesis of β-d-galactofuranosyl nucleoside analogues. A new type of β-d-galactofuranosidase inhibitor

  摘要：

  The development of beta -D-galactofuranosidase inhibitors provides a good chemotherapeutic target for treatment of major human diseases, because beta -D-galactofuranose is a constituent of important pathogen microorganisms but is absent in mammals. With this purpose we have prepared beta -D-galactofuranosyl nucleoside analogues, derived by the addition of nucleophiles to perbenzoylated beta -D-galactofuranosyl isothiocyanate, a compound previously prepared in this laboratory. N-beta -D-Galactofuratlosyl-O-ethylthiourethane N-beta -D-galactofuranosyl-4-oxoimidazolidi N-beta -D-galactofuranosyl-4-imidazoline-2-thione, and N-beta -D-galactofuranosyl-4-methoxyimidazolidine-2-thione, were prepared. The biological assays showed that imidazoline and imidazolidine-2-thione derivatives act as a new type of exo beta -D-galactofuranosidase inhibitor. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00146-x

文献信息

• Synthesis of β-d-galactofuranosyl nucleoside analogues. A new type of β-d-galactofuranosidase inhibitor
  作者：Carla Marino、Pal Herczegh、Rosa M de Lederkremer

  DOI：10.1016/s0008-6215(01)00146-x

  日期：2001.7

  The development of beta -D-galactofuranosidase inhibitors provides a good chemotherapeutic target for treatment of major human diseases, because beta -D-galactofuranose is a constituent of important pathogen microorganisms but is absent in mammals. With this purpose we have prepared beta -D-galactofuranosyl nucleoside analogues, derived by the addition of nucleophiles to perbenzoylated beta -D-galactofuranosyl isothiocyanate, a compound previously prepared in this laboratory. N-beta -D-Galactofuratlosyl-O-ethylthiourethane N-beta -D-galactofuranosyl-4-oxoimidazolidi N-beta -D-galactofuranosyl-4-imidazoline-2-thione, and N-beta -D-galactofuranosyl-4-methoxyimidazolidine-2-thione, were prepared. The biological assays showed that imidazoline and imidazolidine-2-thione derivatives act as a new type of exo beta -D-galactofuranosidase inhibitor. (C) 2001 Elsevier Science Ltd. All rights reserved.