6-hydroxy-3,4-dihydro-1-oxo-2(1H)-isoquinolineacetic acid 1,1-dimethylethyl ester | 164147-68-6

• 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: 6-hydroxy-3,4-dihydro-1-oxo-2(1H)-isoquinolineacetic acid 1,1-dimethylethyl ester
• 英文别名: Tert-butyl 2-(6-hydroxy-1-oxo-3,4-dihydroisoquinolin-2-yl)acetate
• CAS: 164147-68-6
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: DRRKWNDYCMMEQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-hydroxy-3,4-dihydro-1-oxo-2(1H)-isoquinolineacetic acid 1,1-dimethylethyl ester 在 吡啶 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 Methyl 2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1-oxo-3,4-dihydroisoquinoline-6-carboxylate
  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：

  6-(benzyloxy)-3,4-dihydroisoquinolin-1(2H)-one 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙酸乙酯 为溶剂， 反应 4.5h， 生成 6-hydroxy-3,4-dihydro-1-oxo-2(1H)-isoquinolineacetic acid 1,1-dimethylethyl ester
  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