6-(3,4,5-Trimethoxy-benzylcarbamoyl)-1,3-dihydro-isoindole-2,5-dicarboxylic acid 2-tert-butyl ester | 401810-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 6-(3,4,5-Trimethoxy-benzylcarbamoyl)-1,3-dihydro-isoindole-2,5-dicarboxylic acid 2-tert-butyl ester
• CAS: 401810-02-4
• 化学式: C₂₅H₃₀N₂O₈
• 分子量: 486.522
• InChiKey: VFMSFEHZFLYXKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  123.63
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-(3,4,5-Trimethoxy-benzylcarbamoyl)-1,3-dihydro-isoindole-2,5-dicarboxylic acid 2-tert-butyl ester 在 甲酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-N-[2-(4-chlorophenyl)ethyl]-2-[6-[5-[2-(4-chlorophenyl)ethylcarbamoyl]-6-[(3,4,5-trimethoxyphenyl)methylcarbamoyl]-1,3-dihydroisoindol-2-yl]-6-oxohexanoyl]-6-N-[(3,4,5-trimethoxyphenyl)methyl]-1,3-dihydroisoindole-5,6-dicarboxamide
  参考文献：
  名称：

  Erythropoietin Mimetics Derived from Solution Phase Combinatorial Libraries

  摘要：

  The erythropoietin receptor (EPOr) is activated by ligand-induced homodimerization, which leads to the proliferation and differentiation of erythroid progenitors. Through the screening of combinatorial libraries of dimeric iminodiacetic acid diamides, novel small molecule binders of EPOr were identified in a protein binding assay. Evaluation of a series of analogues led to optimization of binding subunits, and these were utilized in the synthesis of higher order dimer, trimer, and tetramer libraries. Several of the most active EPOr binders were found to be partial agonists and induced concentration-dependent proliferation of an EPO-dependent cell line (UT-7/EPO) while having no effect on a cell line lacking the EPOr (FDC-P1). An additional compound library, based on a symmetrical isoindoline-5,6-dicarboxylic acid template and including the optimized binding subunits, was synthesized and screened leading to the identification of additional EPO mimetics.

  DOI：

  10.1021/ja0118789
• 作为产物：
  描述：

  N-BOC-isoindoline-5,6-dicarboxylic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 6-(3,4,5-Trimethoxy-benzylcarbamoyl)-1,3-dihydro-isoindole-2,5-dicarboxylic acid 2-tert-butyl ester
  参考文献：
  名称：

  Erythropoietin Mimetics Derived from Solution Phase Combinatorial Libraries

  摘要：

  The erythropoietin receptor (EPOr) is activated by ligand-induced homodimerization, which leads to the proliferation and differentiation of erythroid progenitors. Through the screening of combinatorial libraries of dimeric iminodiacetic acid diamides, novel small molecule binders of EPOr were identified in a protein binding assay. Evaluation of a series of analogues led to optimization of binding subunits, and these were utilized in the synthesis of higher order dimer, trimer, and tetramer libraries. Several of the most active EPOr binders were found to be partial agonists and induced concentration-dependent proliferation of an EPO-dependent cell line (UT-7/EPO) while having no effect on a cell line lacking the EPOr (FDC-P1). An additional compound library, based on a symmetrical isoindoline-5,6-dicarboxylic acid template and including the optimized binding subunits, was synthesized and screened leading to the identification of additional EPO mimetics.

  DOI：

  10.1021/ja0118789