Tert-butyl 2-[6-[2-(4-carbamimidoylphenyl)ethynyl]-1-oxo-3,4-dihydroisoquinolin-2-yl]acetate | 164147-73-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Tert-butyl 2-[6-[2-(4-carbamimidoylphenyl)ethynyl]-1-oxo-3,4-dihydroisoquinolin-2-yl]acetate
• CAS: 164147-73-3
• 化学式: C₂₄H₂₅N₃O₃
• 分子量: 403.481
• InChiKey: BZXVJJSKNYPHCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-[6-[2-(4-carbamimidoylphenyl)ethynyl]-1-oxo-3,4-dihydroisoquinolin-2-yl]acetate 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 6-[[4-(aminoiminomethyl)phenyl]ethynyl]-3,4-dihydro-1-oxo-2(1H)-isoquinolineacetic acid trifluoroacetate
  参考文献：
  名称：

  Non-Peptide RGD Surrogates Which Mimic a Gly-Asp β-Turn:  Potent Antagonists of Platelet Glycoprotein IIb−IIIa

  摘要：

  Cyclic heptapeptide 1, which contains an Arg-Gly-Asp sequence, has good affinity for the platelet receptor GPIIb-IIIa and was chosen for study by H-1 NMR techniques. The key RGD sequence of this molecule was found to reside in a conformationally defined type II' Gly-Asp beta-turn, and this information was used in the design of simple non-peptide RGD mimics. Disubstituted isoquinolones, bearing an acidic side chain at position 2 and a basic side chain at position 6, were prepared and were found to have modest affinity for GPIIb-IIIa. Systematic modification of the basic residue contained in these molecules yielded compounds with high affinity for GPIIb-IIIa.

  DOI：

  10.1021/jm9701076
• 作为产物：
  描述：

  Tert-butyl 2-[1-oxo-6-(trifluoromethylsulfonyloxy)-3,4-dihydroisoquinolin-2-yl]acetate 在 吡啶 、 bis(triphenylphosphine)palladium(II)-chloride 、 硫化氢 、 ammonium acetate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 52.0h， 生成 Tert-butyl 2-[6-[2-(4-carbamimidoylphenyl)ethynyl]-1-oxo-3,4-dihydroisoquinolin-2-yl]acetate
  参考文献：
  名称：

  Non-Peptide RGD Surrogates Which Mimic a Gly-Asp β-Turn:  Potent Antagonists of Platelet Glycoprotein IIb−IIIa

  摘要：

  Cyclic heptapeptide 1, which contains an Arg-Gly-Asp sequence, has good affinity for the platelet receptor GPIIb-IIIa and was chosen for study by H-1 NMR techniques. The key RGD sequence of this molecule was found to reside in a conformationally defined type II' Gly-Asp beta-turn, and this information was used in the design of simple non-peptide RGD mimics. Disubstituted isoquinolones, bearing an acidic side chain at position 2 and a basic side chain at position 6, were prepared and were found to have modest affinity for GPIIb-IIIa. Systematic modification of the basic residue contained in these molecules yielded compounds with high affinity for GPIIb-IIIa.

  DOI：

  10.1021/jm9701076