6-(2-N-tert-butoxycarbonyl-N-methyl-aminothiazol-5-yl)-1-(N,N-dimethylsulfamoyl)-benzimidazole | 479198-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 6-(2-N-tert-butoxycarbonyl-N-methyl-aminothiazol-5-yl)-1-(N,N-dimethylsulfamoyl)-benzimidazole
• 英文别名: tert-butyl N-[5-[3-(dimethylsulfamoyl)benzimidazol-5-yl]-1,3-thiazol-2-yl]-N-methylcarbamate
• CAS: 479198-83-9
• 化学式: C₁₈H₂₃N₅O₄S₂
• 分子量: 437.544
• InChiKey: LUDJNCKJROZMLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-(2-N-tert-butoxycarbonyl-N-methyl-aminothiazol-5-yl)-1-(N,N-dimethylsulfamoyl)-benzimidazole 在 4-二甲氨基吡啶 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 Methanesulfonic acid (R)-1-{6-[2-(tert-butoxycarbonyl-methyl-amino)-thiazol-5-yl]-1-dimethylsulfamoyl-1H-benzoimidazol-2-yl}-2-[(4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester
  参考文献：
  名称：

  Synthesis, Incorporation into Triplex-Forming Oligonucleotide, and Binding Properties of a Novel 2‘-Deoxy-C-Nucleoside Featuring a 6-(Thiazolyl-5)benzimidazole Nucleobase

  摘要：

  6-(Thiazolyl-5)benzimidazole (B-1) was designed as a novel nucleobase for the specific recognition of an inverted A(.)T base pair in a triple helix motif. It was successfully incorporated into an 18-mer triplex-forming oligonucleotide (TFO) using the 2'-deoxy-C-nucleoside phosphoramidite 16. The triple helix binding properties of the modified TFO were examined by means of thermal denaturation experiments targeting an oligopyrimidine-oligopurine 26-mer DNA duplex containing an A-T base pair inversion.

  DOI：

  10.1021/ol026609h
• 作为产物：
  描述：

  2-(N-tert-butoxycarbonyl-N-methyl-amino)-5-tributyltin-thiazole 、 6-iodo-1-(N,N-dimethylsulfamoyl)-benzimidazole 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到6-(2-N-tert-butoxycarbonyl-N-methyl-aminothiazol-5-yl)-1-(N,N-dimethylsulfamoyl)-benzimidazole
  参考文献：
  名称：

  Synthesis, Incorporation into Triplex-Forming Oligonucleotide, and Binding Properties of a Novel 2‘-Deoxy-C-Nucleoside Featuring a 6-(Thiazolyl-5)benzimidazole Nucleobase

  摘要：

  6-(Thiazolyl-5)benzimidazole (B-1) was designed as a novel nucleobase for the specific recognition of an inverted A(.)T base pair in a triple helix motif. It was successfully incorporated into an 18-mer triplex-forming oligonucleotide (TFO) using the 2'-deoxy-C-nucleoside phosphoramidite 16. The triple helix binding properties of the modified TFO were examined by means of thermal denaturation experiments targeting an oligopyrimidine-oligopurine 26-mer DNA duplex containing an A-T base pair inversion.

  DOI：

  10.1021/ol026609h