2-[1-(3-methoxyphenyl)ethoxy]-1H-isoindole-1,3(2H)-dione | 630108-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[1-(3-methoxyphenyl)ethoxy]-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[1-(3-Methoxyphenyl)ethoxy]isoindole-1,3-dione；2-[1-(3-methoxyphenyl)ethoxy]isoindole-1,3-dione
• CAS: 630108-36-0
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: UVNOHAYOZVMSGX-UHFFFAOYSA-N

物化性质

• 沸点：
  446.5±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  2-[1-(3-methoxyphenyl)ethoxy]-1H-isoindole-1,3(2H)-dione 在 肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以95%的产率得到1-[1-(aminooxy)ethyl]-3-methoxybenzene
  参考文献：
  名称：

  Synthesis of new arylalkoxy amido derivatives as melatoninergic ligands

  摘要：

  Amido derivatives 10-18 of the corresponding oxyamines were synthesised as melatoninergic ligands by the reaction of hydroxyphtalimide with the halogeno derivatives or the corresponding alcohols using Mitsunobu reaction conditions. The affinity of the compounds for chicken brain melatonin receptors and recombinant human MT1 and MT2 receptors was evaluated using 2-[I-125]-iodomelatonin as the radioligand. Overall, the introduction of an oxygen atom in the amido chain was not a favourable parameter as the compounds were less potent than the corresponding deoxy derivatives. However, nanomolar compounds were obtained with the arylethyloxy derivatives (13c (R' = nPr), chicken brain, hMT(1), hMT(2), K-i values: 4.8, 3.86, 2.4 nM, respectively) and the 2,7-dimethoxynaphthalene derivatives (17c (R' = nPr), chicken brain, hMT(1), hMT(2), K-i values: 0.04, 0.13, 0.1 nM, respectively). The functional activity of these compounds was evaluated by the aggregation of melanophores in Xenopus laevis tadpoles and the potency was related to the affinity of the molecules for melatonin receptors. The compounds were found to be full agonists and compound 17a was 20-fold more potent than melatonin in this bioassay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00328-0
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 1-(3-甲氧基苯基)乙醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以92%的产率得到2-[1-(3-methoxyphenyl)ethoxy]-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis of new arylalkoxy amido derivatives as melatoninergic ligands

  摘要：

  Amido derivatives 10-18 of the corresponding oxyamines were synthesised as melatoninergic ligands by the reaction of hydroxyphtalimide with the halogeno derivatives or the corresponding alcohols using Mitsunobu reaction conditions. The affinity of the compounds for chicken brain melatonin receptors and recombinant human MT1 and MT2 receptors was evaluated using 2-[I-125]-iodomelatonin as the radioligand. Overall, the introduction of an oxygen atom in the amido chain was not a favourable parameter as the compounds were less potent than the corresponding deoxy derivatives. However, nanomolar compounds were obtained with the arylethyloxy derivatives (13c (R' = nPr), chicken brain, hMT(1), hMT(2), K-i values: 4.8, 3.86, 2.4 nM, respectively) and the 2,7-dimethoxynaphthalene derivatives (17c (R' = nPr), chicken brain, hMT(1), hMT(2), K-i values: 0.04, 0.13, 0.1 nM, respectively). The functional activity of these compounds was evaluated by the aggregation of melanophores in Xenopus laevis tadpoles and the potency was related to the affinity of the molecules for melatonin receptors. The compounds were found to be full agonists and compound 17a was 20-fold more potent than melatonin in this bioassay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00328-0

文献信息

• Synthesis of new arylalkoxy amido derivatives as melatoninergic ligands
  作者：Cécile Pégurier、Laurence Morellato、Eminn Chahed、Jean Andrieux、Jean-Paul Nicolas、Jean A Boutin、Caroline Bennejean、Philippe Delagrange、Michel Langlois、Monique Mathé-Allainmat

  DOI：10.1016/s0968-0896(02)00328-0

  日期：2003.3

  Amido derivatives 10-18 of the corresponding oxyamines were synthesised as melatoninergic ligands by the reaction of hydroxyphtalimide with the halogeno derivatives or the corresponding alcohols using Mitsunobu reaction conditions. The affinity of the compounds for chicken brain melatonin receptors and recombinant human MT1 and MT2 receptors was evaluated using 2-[I-125]-iodomelatonin as the radioligand. Overall, the introduction of an oxygen atom in the amido chain was not a favourable parameter as the compounds were less potent than the corresponding deoxy derivatives. However, nanomolar compounds were obtained with the arylethyloxy derivatives (13c (R' = nPr), chicken brain, hMT(1), hMT(2), K-i values: 4.8, 3.86, 2.4 nM, respectively) and the 2,7-dimethoxynaphthalene derivatives (17c (R' = nPr), chicken brain, hMT(1), hMT(2), K-i values: 0.04, 0.13, 0.1 nM, respectively). The functional activity of these compounds was evaluated by the aggregation of melanophores in Xenopus laevis tadpoles and the potency was related to the affinity of the molecules for melatonin receptors. The compounds were found to be full agonists and compound 17a was 20-fold more potent than melatonin in this bioassay. (C) 2002 Elsevier Science Ltd. All rights reserved.