Tert-butyl 2-[1-oxo-6-(trifluoromethylsulfonyloxy)-3,4-dihydroisoquinolin-2-yl]acetate | 164147-71-1

• 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-[1-oxo-6-(trifluoromethylsulfonyloxy)-3,4-dihydroisoquinolin-2-yl]acetate
• CAS: 164147-71-1
• 化学式: C₁₆H₁₈F₃NO₆S
• 分子量: 409.383
• InChiKey: STVXHFACOMGROU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-[1-oxo-6-(trifluoromethylsulfonyloxy)-3,4-dihydroisoquinolin-2-yl]acetate 在 palladium on activated charcoal 吡啶 、 bis(triphenylphosphine)palladium(II)-chloride 、 硫化氢 、 ammonium acetate 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 57.0h， 生成 6-[2-[4-(aminoiminomethyl)phenyl]ethyl]-3,4-dihydro-1-oxo-2(1H)-isoquinoline acetic 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：

  6-羟基-3,4-二氢异喹啉-1(2H)-酮 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 20.5h， 生成 Tert-butyl 2-[1-oxo-6-(trifluoromethylsulfonyloxy)-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

文献信息

• Non-Peptide RGD Surrogates Which Mimic a Gly-Asp β-Turn:  Potent Antagonists of Platelet Glycoprotein IIb−IIIa
  作者：Matthew J. Fisher、Bruce Gunn、Cathy S. Harms、Allen D. Kline、Jeffrey T. Mullaney、Anne Nunes、Robert M. Scarborough、Ann E. Arfsten、Marshall A. Skelton、Suzane L. Um、Barbara G. Utterback、Joseph A. Jakubowski

  DOI：10.1021/jm9701076

  日期：1997.6.1

  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.