{6-[4-(tert-Butoxycarbonylamino-imino-methyl)-benzyloxy]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid tert-butyl ester | 181073-12-1

• 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: {6-[4-(tert-Butoxycarbonylamino-imino-methyl)-benzyloxy]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid tert-butyl ester
• 英文别名: tert-butyl 2-[6-[[4-[N'-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]phenyl]methoxy]-1-oxo-3,4-dihydroisoquinolin-2-yl]acetate
• CAS: 181073-12-1
• 化学式: C₂₈H₃₅N₃O₆
• 分子量: 509.602
• InChiKey: KNNAOMHNVXFPMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 {6-[4-(tert-Butoxycarbonylamino-imino-methyl)-benzyloxy]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid tert-butyl ester 反应 1.0h， 以0.31 g的产率得到6-[[4-(aminoiminomethyl)phenyl]methoxy]-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：

  6-(benzyloxy)-3,4-dihydroisoquinolin-1(2H)-one 在 palladium on activated charcoal 吡啶 、 硫化氢 、 ammonium acetate 、 氢气 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 丙酮 为溶剂， 反应 61.5h， 生成 {6-[4-(tert-Butoxycarbonylamino-imino-methyl)-benzyloxy]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid tert-butyl 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