4-{1-[2-(2,2-Dimethyl-propionylamino)-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl]-vinyl}-benzoic acid methyl ester | 199535-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-{1-[2-(2,2-Dimethyl-propionylamino)-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl]-vinyl}-benzoic acid methyl ester
• CAS: 199535-41-6
• 化学式: C₂₄H₂₅N₃O₄
• 分子量: 419.48
• InChiKey: CLJYJHHPERLSIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  101.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-{1-[2-(2,2-Dimethyl-propionylamino)-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl]-vinyl}-benzoic acid methyl ester 在 lithium hydroxide 、 二苯基膦叠氮化物 、 溴 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 86.5h， 生成 (2RS)-N-{4-[3-(2-amino-3,4-dihydro-4-oxo-quinazolin-6-yl)-1,2-dibromo-prop-2-yl]benzoyl}-L-glutamic acid trifluoroacetate
  参考文献：
  名称：

  Functionalized analogues of 5,8,10-trideazafolate: Development of an enzyme-assembled tight binding inhibitor of GAR Tfase and a potential irreversible inhibitor of AICAR Tfase

  摘要：

  A set of inhibitors 3 and 4 of GAR and AICAR Tfase based on the TDAF core which contain an sp(2) C-10 carbon atom replacing N-10 of the natural cofactor are detailed. Both possess electrophilic olefins and the potential of trapping the reacting amine of the substrates GAR and AICAR by a Michael addition at the enzyme active site to provide an enzyme-assembled tight binding inhibitor. While these agents did not display such characteristics and served as simple competitive inhibitors of GAR Tfase and AICAR Tfase, inhibitor 15 prepared in the conversion of 3 to 4 may provide an enzyme-assembled tight binding inhibitor of GAR Tfase upon reaction with the substrate GAR and may inactivate AICAR Tfase by virtue of alkylation of an active site residue. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00122-3
• 作为产物：
  描述：

  4-{2-[2-(2,2-Dimethyl-propionylamino)-4-oxo-3,4-dihydro-quinazolin-6-yl]-1-methanesulfonyloxymethyl-ethyl}-benzoic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以68%的产率得到4-{1-[2-(2,2-Dimethyl-propionylamino)-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl]-vinyl}-benzoic acid methyl ester
  参考文献：
  名称：

  Functionalized analogues of 5,8,10-trideazafolate: Development of an enzyme-assembled tight binding inhibitor of GAR Tfase and a potential irreversible inhibitor of AICAR Tfase

  摘要：

  A set of inhibitors 3 and 4 of GAR and AICAR Tfase based on the TDAF core which contain an sp(2) C-10 carbon atom replacing N-10 of the natural cofactor are detailed. Both possess electrophilic olefins and the potential of trapping the reacting amine of the substrates GAR and AICAR by a Michael addition at the enzyme active site to provide an enzyme-assembled tight binding inhibitor. While these agents did not display such characteristics and served as simple competitive inhibitors of GAR Tfase and AICAR Tfase, inhibitor 15 prepared in the conversion of 3 to 4 may provide an enzyme-assembled tight binding inhibitor of GAR Tfase upon reaction with the substrate GAR and may inactivate AICAR Tfase by virtue of alkylation of an active site residue. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00122-3