3-(氨基甲基)-5,6-二羟基-3H-2-苯并呋喃-1-酮氢溴酸盐 | 78219-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(氨基甲基)-5,6-二羟基-3H-2-苯并呋喃-1-酮氢溴酸盐
• 英文名称: 1-(aminomethyl)-5,6-dihydroxyphthalide hydrobromide
• 英文别名: 3-aminomethyl-5,6-dihydroxy-phthalide; hydrobromide；3-Aminomethyl-5,6-dihydroxy-phthalid; Hydrobromid；3-(aminomethyl)-5,6-dihydroxy-3H-2-benzofuran-1-one;hydron;bromide
• CAS: 78219-03-1
• 化学式: BrH*C₉H₉NO₄
• 分子量: 276.087
• InChiKey: ZOXXBHYZISKNTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.8
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  3-(氨基甲基)-5,6-二羟基-3H-2-苯并呋喃-1-酮氢溴酸盐 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以54%的产率得到1-(aminomethyl)-5,6-dihydroxyphthalan hydrobromide
  参考文献：
  名称：

  Conformationally defined adrenergic agents. 4. 1-(Aminomethyl)phthalans: synthesis and pharmacological consequences of the phthalan ring oxygen atom

  摘要：

  The synthesis of a series of 1-(aminomethyl)phthalans 1b is reported. The radioligand binding to alpha 1- and alpha 2-receptors and the in vitro pharmacology in alpha 1 (rabbit aorta) and alpha 2 (phenoxybenzamine-pretreated dog saphenous vein) tissues were determined and were compared to the activity of the corresponding 1-(aminomethyl)indans. The activity of this series of phthalans was found to be consistent with the electrostatic repulsion hypothesis that was used to design the parent indan (ERBCOP) compounds. The effect of the phthalan ring oxygenation was to somewhat improve alpha 1-receptor potency relative to the 6-ERBCOP indans without having a general effect on the alpha 2-receptor potency. We conclude from the overall pattern of activity that while the norepinephrine type beta-hydroxyl group may be beneficial for binding to the alpha 1-adrenoceptor, it is not required for strong binding to or full stimulation of the alpha 2-adrenergic receptor, provided that the conformational mobility associated with the phenylethylamine is restricted and maintained in a favorable conformation for receptor interaction.

  DOI：

  10.1021/jm00384a030
• 作为产物：
  描述：

  4,5-二甲氧基邻苯二甲酸 在 palladium on activated charcoal sodium hydroxide 、 氢溴酸 、 氢气 作用下， 反应 4.5h， 生成 3-(氨基甲基)-5,6-二羟基-3H-2-苯并呋喃-1-酮氢溴酸盐
  参考文献：
  名称：

  Conformationally defined adrenergic agents. 4. 1-(Aminomethyl)phthalans: synthesis and pharmacological consequences of the phthalan ring oxygen atom

  摘要：

  The synthesis of a series of 1-(aminomethyl)phthalans 1b is reported. The radioligand binding to alpha 1- and alpha 2-receptors and the in vitro pharmacology in alpha 1 (rabbit aorta) and alpha 2 (phenoxybenzamine-pretreated dog saphenous vein) tissues were determined and were compared to the activity of the corresponding 1-(aminomethyl)indans. The activity of this series of phthalans was found to be consistent with the electrostatic repulsion hypothesis that was used to design the parent indan (ERBCOP) compounds. The effect of the phthalan ring oxygenation was to somewhat improve alpha 1-receptor potency relative to the 6-ERBCOP indans without having a general effect on the alpha 2-receptor potency. We conclude from the overall pattern of activity that while the norepinephrine type beta-hydroxyl group may be beneficial for binding to the alpha 1-adrenoceptor, it is not required for strong binding to or full stimulation of the alpha 2-adrenergic receptor, provided that the conformational mobility associated with the phenylethylamine is restricted and maintained in a favorable conformation for receptor interaction.

  DOI：

  10.1021/jm00384a030

文献信息

• Synthese von neuen, pharmakologisch wirksamen 1-Amino-1-[phthalidyl-(3)]-alkanen
  作者：Dénes Beke、Csaba Szántay

  DOI：10.1002/ardp.19582910706

  日期：——
• DEBERNARDIS J. F.; ARENDSEN D. L.; KYNCL J. J.; KERKMAN D. J., J. MED. CHEM., 30,(1987) N 1, 178-184
  作者：DEBERNARDIS J. F.、 ARENDSEN D. L.、 KYNCL J. J.、 KERKMAN D. J.

  DOI：——

  日期：——
• Conformationally defined adrenergic agents. 4. 1-(Aminomethyl)phthalans: synthesis and pharmacological consequences of the phthalan ring oxygen atom
  作者：John F. DeBernardis、David L. Arendsen、John J. Kyncl、Daniel J. Kerkman

  DOI：10.1021/jm00384a030

  日期：1987.1

  The synthesis of a series of 1-(aminomethyl)phthalans 1b is reported. The radioligand binding to alpha 1- and alpha 2-receptors and the in vitro pharmacology in alpha 1 (rabbit aorta) and alpha 2 (phenoxybenzamine-pretreated dog saphenous vein) tissues were determined and were compared to the activity of the corresponding 1-(aminomethyl)indans. The activity of this series of phthalans was found to be consistent with the electrostatic repulsion hypothesis that was used to design the parent indan (ERBCOP) compounds. The effect of the phthalan ring oxygenation was to somewhat improve alpha 1-receptor potency relative to the 6-ERBCOP indans without having a general effect on the alpha 2-receptor potency. We conclude from the overall pattern of activity that while the norepinephrine type beta-hydroxyl group may be beneficial for binding to the alpha 1-adrenoceptor, it is not required for strong binding to or full stimulation of the alpha 2-adrenergic receptor, provided that the conformational mobility associated with the phenylethylamine is restricted and maintained in a favorable conformation for receptor interaction.