N-[1-(3-Dimethylamino-propyl)-8-hydroxymethyl-1,7,8,9-tetrahydro-chromeno[5,6-d]imidazol-2-yl]-benzamide | 870771-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-[1-(3-Dimethylamino-propyl)-8-hydroxymethyl-1,7,8,9-tetrahydro-chromeno[5,6-d]imidazol-2-yl]-benzamide
• CAS: 870771-90-7
• 化学式: C₂₃H₂₈N₄O₃
• 分子量: 408.5
• InChiKey: OWWXKAFKGUBIHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  79.62
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[1-(3-Dimethylamino-propyl)-8-hydroxymethyl-1,7,8,9-tetrahydro-chromeno[5,6-d]imidazol-2-yl]-benzamide 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以396 mg的产率得到[2-Amino-1-(3-dimethylamino-propyl)-1,7,8,9-tetrahydro-chromeno[5,6-d]imidazol-8-yl]-methanol
  参考文献：
  名称：

  SAR by MS:  Discovery of a New Class of RNA-Binding Small Molecules for the Hepatitis C Virus:  Internal Ribosome Entry Site IIA Subdomain

  摘要：

  A new class of small molecules that bind the HCV RNA IRES IIA subdomain with sub-micromolar affinity is reported. The benzimidazole 'hit' 1 with a K-D similar to 100 mu M to a 29-mer RNA model of Domain IIA was identified from a 180000-member library using mass spectrometry-based screening methods. Further MS-assisted SAR (structure-activity relationships) studies afforded benzimidazole derivatives with sub-micromolar binding affinity for the IIA RNA construct. The optimized benzimidazoles demonstrated activity in a cellular replicon assay at concentrations comparable to their K-D for the RNA target.

  DOI：

  10.1021/jm050815o
• 作为产物：
  描述：

  Acetic acid 2-acetoxymethyl-3-(2,6-difluoro-3-nitro-phenyl)-propyl ester 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 calcium carbonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 146.0h， 生成 N-[1-(3-Dimethylamino-propyl)-8-hydroxymethyl-1,7,8,9-tetrahydro-chromeno[5,6-d]imidazol-2-yl]-benzamide
  参考文献：
  名称：

  SAR by MS:  Discovery of a New Class of RNA-Binding Small Molecules for the Hepatitis C Virus:  Internal Ribosome Entry Site IIA Subdomain

  摘要：

  A new class of small molecules that bind the HCV RNA IRES IIA subdomain with sub-micromolar affinity is reported. The benzimidazole 'hit' 1 with a K-D similar to 100 mu M to a 29-mer RNA model of Domain IIA was identified from a 180000-member library using mass spectrometry-based screening methods. Further MS-assisted SAR (structure-activity relationships) studies afforded benzimidazole derivatives with sub-micromolar binding affinity for the IIA RNA construct. The optimized benzimidazoles demonstrated activity in a cellular replicon assay at concentrations comparable to their K-D for the RNA target.

  DOI：

  10.1021/jm050815o