Methanesulfonic acid 2-amino-1-(3-dimethylamino-propyl)-7,8-dihydro-1H-6-oxa-1,3-diaza-as-indacen-7-ylmethyl ester | 870771-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: Methanesulfonic acid 2-amino-1-(3-dimethylamino-propyl)-7,8-dihydro-1H-6-oxa-1,3-diaza-as-indacen-7-ylmethyl ester
• CAS: 870771-96-3
• 化学式: C₁₆H₂₄N₄O₄S
• 分子量: 368.457
• InChiKey: OWVMWQJWODXVOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid 2-amino-1-(3-dimethylamino-propyl)-7,8-dihydro-1H-6-oxa-1,3-diaza-as-indacen-7-ylmethyl ester 、 二甲胺 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以969 mg的产率得到Isis-11
  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：

  2,2-Dimethyl-propionic acid 4-(3-dimethylamino-propylamino)-5-nitro-2,3-dihydro-benzofuran-2-ylmethyl ester 在 盐酸 、 氢气 、 镍 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 Methanesulfonic acid 2-amino-1-(3-dimethylamino-propyl)-7,8-dihydro-1H-6-oxa-1,3-diaza-as-indacen-7-ylmethyl ester
  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