7-(benzyloxy)-3,4-dihydroisoquinolin-1(2H)-one | 190604-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 7-(benzyloxy)-3,4-dihydroisoquinolin-1(2H)-one
• 英文别名: 7-phenylmethoxy-3,4-dihydro-2H-isoquinolin-1-one
• CAS: 190604-11-6
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: ONWFTZCTVKFYIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  521.5±50.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(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 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 hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 7-(benzyloxy)-3,4-dihydroisoquinolin-1(2H)-one
  参考文献：
  名称：

  含有杂环的新型 3,4-二氢异喹啉衍生物作为潜在抗惊厥药的合成与药理学评价

  摘要：

  合成了两个具有杂环衍生物的新型 3,4-二氢异喹啉系列（4a-t 和 9a-e），并使用最大电休克 (MES) 测试和戊四唑 (PTZ) 诱导的癫痫发作测试评估了它们的抗惊厥活性。所有化合物均通过 IR、1H-NMR、13C-NMR 和质谱数据进行表征。其中，9-(exyloxy)-5,6-dihydro-[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (9a) 在 MES 试验中显示出显着的抗惊厥活性ED50 值为 63.31 mg/kg，具有保护指数（PI > 7.9）的安全范围。它显示出比丙戊酸盐高得多的抗惊厥活性。它还显示出针对 PTZ 诱发的癫痫发作的有效活性。

  DOI：

  10.3390/molecules21121635

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.
• Synthesis and Pharmacological Evaluation of New 3,4-Dihydroisoquinolin Derivatives Containing Heterocycle as Potential Anticonvulsant Agents
  作者：Hong-Jian Zhang、Qing-Kun Shen、Chun-Mei Jin、Zhe-Shan Quan

  DOI：10.3390/molecules21121635

  日期：——

  Two novel series of 3,4-dihydroisoquinolin with heterocycle derivatives (4a–t and 9a–e) were synthesized and evaluated for their anticonvulsant activity using maximal electroshock (MES) test and pentylenetetrazole (PTZ)-induced seizure test. All compounds were characterized by IR, 1H-NMR, 13C-NMR, and mass spectral data. Among them, 9-(exyloxy)-5,6-dihydro-[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one

  合成了两个具有杂环衍生物的新型 3,4-二氢异喹啉系列（4a-t 和 9a-e），并使用最大电休克 (MES) 测试和戊四唑 (PTZ) 诱导的癫痫发作测试评估了它们的抗惊厥活性。所有化合物均通过 IR、1H-NMR、13C-NMR 和质谱数据进行表征。其中，9-(exyloxy)-5,6-dihydro-[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (9a) 在 MES 试验中显示出显着的抗惊厥活性ED50 值为 63.31 mg/kg，具有保护指数（PI > 7.9）的安全范围。它显示出比丙戊酸盐高得多的抗惊厥活性。它还显示出针对 PTZ 诱发的癫痫发作的有效活性。