8-methyl-2-[(3-nitrophenyl)amino]-6-oxo-3-[2-(1-pyrrolidinyl)ethyl]-6H-pyrano[2,3-f]benzimidazole-7-carboxamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-methyl-2-[(3-nitrophenyl)amino]-6-oxo-3-[2-(1-pyrrolidinyl)ethyl]-6H-pyrano[2,3-f]benzimidazole-7-carboxamide
• 英文别名: 8-Methyl-2-(3-nitroanilino)-6-oxo-3-(2-pyrrolidin-1-ylethyl)pyrano[3,2-f]benzimidazole-7-carboxamide；8-methyl-2-(3-nitroanilino)-6-oxo-3-(2-pyrrolidin-1-ylethyl)pyrano[3,2-f]benzimidazole-7-carboxamide
• 化学式: C₂₄H₂₄N₆O₅
• 分子量: 476.492
• InChiKey: QXRVIWLNBVPSBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-fluoro-4-methyl-6-nitro-2-oxo-2H-1-benzopyran-3-carboxylic acid 、 1-(2-氨乙基)吡咯烷 、 3-硝基异硫氰酸苯酯 以70%的产率得到8-methyl-2-[(3-nitrophenyl)amino]-6-oxo-3-[2-(1-pyrrolidinyl)ethyl]-6H-pyrano[2,3-f]benzimidazole-7-carboxamide
  参考文献：
  名称：

  Parallel solid-phase synthesis of 2-arylamino-6H-pyrano[2,3-f]benzimidazole-6-ones

  摘要：

  The parallel solid-phase synthesis of a hydrophilic psoralen analogue, 2-arylamino-6H-pyrano[2,3-f]benzimidazole-6-ones (2-arylaminoimidazocoumarins), has been developed. The resin-bound 7-fluoro-4-methyl-6-nitro-2-oxo-2H-1-benzopyran-3-carboxylic acid underwent aromatic substitution with primary amines, followed by reduction of the nitro group with tin(II) chloride. The cyclization of the o-dianilino intermediates was accomplished with aryl isothiocyanates in the presence of 1,3-diisopropylcarbodiimide (DIC). The final products were released from the resin with trifluoroacetic acid (TFA) and obtained in high purity and good isolated yield. The 2-arylaminoimidazocoumarins exhibit interesting spectral properties. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.102

文献信息

• [EN] ABETA-BINDING SMALL MOLECULES<br/>[FR] PETITES MOLÉCULES SE LIANT À ABETA
  申请人：UNIV CALIFORNIA

  公开号：WO2009059214A1

  公开（公告）日：2009-05-07

  In one aspect, the present invention provides for compounds and labeled compounds of Formula I, and pharmaceutical compositions thereof. In another aspect, the present invention provides for methods of using compounds or labeled compounds of Formula I for various therapeutic and imaging purposes, including, but not limited to, treating Alzheimer's disease in patient and imaging Aβ peptide aggregates in a patient.
• Parallel solid-phase synthesis of 2-arylamino-6H-pyrano[2,3-f]benzimidazole-6-ones
  作者：Aimin Song、Kit S. Lam

  DOI：10.1016/j.tet.2004.05.102

  日期：2004.9

  The parallel solid-phase synthesis of a hydrophilic psoralen analogue, 2-arylamino-6H-pyrano[2,3-f]benzimidazole-6-ones (2-arylaminoimidazocoumarins), has been developed. The resin-bound 7-fluoro-4-methyl-6-nitro-2-oxo-2H-1-benzopyran-3-carboxylic acid underwent aromatic substitution with primary amines, followed by reduction of the nitro group with tin(II) chloride. The cyclization of the o-dianilino intermediates was accomplished with aryl isothiocyanates in the presence of 1,3-diisopropylcarbodiimide (DIC). The final products were released from the resin with trifluoroacetic acid (TFA) and obtained in high purity and good isolated yield. The 2-arylaminoimidazocoumarins exhibit interesting spectral properties. (C) 2004 Elsevier Ltd. All rights reserved.