6-(2-N-tert-butoxycarbonyl-N-methyl-aminothiazole-5-yl)-2-(2'-deoxy-β-D-ribofuranosyl-1')-1-(N,N-dimethylsulfamoyl)-benzimidazole | 479198-96-4

• 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-aminothiazole-5-yl)-2-(2'-deoxy-β-D-ribofuranosyl-1')-1-(N,N-dimethylsulfamoyl)-benzimidazole
• 英文别名: tert-butyl N-[5-[3-(dimethylsulfamoyl)-2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]benzimidazol-5-yl]-1,3-thiazol-2-yl]-N-methylcarbamate
• CAS: 479198-96-4
• 化学式: C₂₃H₃₁N₅O₇S₂
• 分子量: 553.66
• InChiKey: ZOJUQSHLOHFPAH-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  184
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-(2-N-tert-butoxycarbonyl-N-methyl-aminothiazole-5-yl)-2-(2'-deoxy-β-D-ribofuranosyl-1')-1-(N,N-dimethylsulfamoyl)-benzimidazole 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 [5-(2-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-tetrahydro-furan-2-yl}-3-dimethylsulfamoyl-3H-benzoimidazol-5-yl)-thiazol-2-yl]-methyl-carbamic acid tert-butyl 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：

  6-(2-N-tert-butoxycarbonyl-N-methyl-aminothiazol-5-yl)-1-(N,N-dimethylsulfamoyl)-benzimidazole 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 、 tin(ll) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 22.25h， 生成 6-(2-N-tert-butoxycarbonyl-N-methyl-aminothiazole-5-yl)-2-(2'-deoxy-β-D-ribofuranosyl-1')-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