(7-Benzyloxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid tert-butyl ester | 190604-12-7

• 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: (7-Benzyloxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid tert-butyl ester
• 英文别名: Tert-butyl 2-(1-oxo-7-phenylmethoxy-3,4-dihydroisoquinolin-2-yl)acetate
• CAS: 190604-12-7
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: LJWWMFMAHKOMTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (7-Benzyloxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 生成 7-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
• 作为产物：
  描述：

  7-甲氧基-3,4-二氢-2H-异喹啉-1-酮 在 三溴化硼 、 sodium hydride 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 33.0h， 生成 (7-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

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.