1-(aminomethyl)-4,5-(methylenedioxy)phthalan hydrochloride | 96142-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-(aminomethyl)-4,5-(methylenedioxy)phthalan hydrochloride
• 英文别名: 1-aminomethyl-4,5-methylenedioxy-phthalan hydrochloride；6,8-Dihydrofuro[3,4-g][1,3]benzodioxol-6-ylmethanamine;hydrochloride
• CAS: 96142-82-4
• 化学式: C₁₀H₁₁NO₃*ClH
• 分子量: 229.663
• InChiKey: WNCXNGLDDROCEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  53.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(aminomethyl)-4,5-(methylenedioxy)phthalan hydrochloride 在 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 1-(aminomethyl)-4,5-dihydroxyphthalan hydrobromide
  参考文献：
  名称：

  Substituted 1-aminomethyl-phthalans

  摘要：

  本文揭示了由以下公式表示的1-氨甲基-邻苯二甲酰亚胺：##STR1##其中R，R.sub.1和R.sub.2独立地选自氢，羟基，1至3个碳原子的低烷氧基，1至3个碳原子的低烯氧基，硫甲基，卤素或##STR2##其中R.sub.5和R.sub.6独立地选自氢，1至4个碳原子的低酰基或式中的磺酰基##STR3##其中R.sub.7是1至4个碳原子的低烷基；或R和R.sub.1，或R.sub.1和R.sub.2可以结合成亚甲二氧或乙亚二氧桥；但必须至少有R，R.sub.1或R.sub.2中的一个不是氢；且R.sub.3和R.sub.4独立地选自氢；1至4个碳原子的低烷基；1至4个碳原子的卤代低烷基；式中的苯基烷基##STR4##其中m为0，1或2，p为0或1，R.sub.8为氢或1至4个碳原子的低烷基，R.sub.9和R.sub.10独立地选自氢，羟基，甲氧基，1至4个碳原子的低烷基或卤素，或R.sub.9和R.sub.10可以结合成亚甲二氧或乙亚二氧桥；或1,4-苯并二氧杂环的式子##STR5##其中q为1，2或3，R.sub.11为氢，甲氧基或卤素；或R.sub.3和R.sub.4可以结合成哌嗪，哌啶或吗啉基团；以及其药物可接受的盐。还揭示了包含式(I)化合物和药物可接受的载体或稀释剂的制药组合物。

  公开号：

  US04500543A1
• 作为产物：
  描述：

  5-formyl-benzo[1,3]dioxole-4-carboxylic acid 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 硼烷四氢呋喃络合物 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 50.0 ℃ 、303.98 kPa 条件下， 反应 22.0h， 生成 1-(aminomethyl)-4,5-(methylenedioxy)phthalan hydrochloride
  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

• Substituted 1-aminomethyl-phthalans
  申请人：Abbott Laboratories

  公开号：US04500543A1

  公开（公告）日：1985-02-19

  Disclosed herein are 1-aminomethyl-phthalans represented by the formula ##STR1## wherein R, R.sub.1, and R.sub.2 are independently selected from hydrogen, hydroxy, loweralkoxy of 1 to 3 carbon atoms, loweralkenyloxy of 1 to 3 carbon atoms, thiomethyl, halo, or ##STR2## wherein R.sub.5 and R.sub.6 are independently selected from hydrogen, loweracyl of 1 to 4 carbon atoms or sulfonyl of the formula ##STR3## wherein R.sub.7 is loweralkyl of 1 to 4 carbon atoms; or R and R.sub.1, or R.sub.1 and R.sub.2 can be taken together to form a methylenedioxy or ethylenedioxy bridge; with the proviso that at least one of R, R.sub.1 or R.sub.2 must be other than hydrogen; and R.sub.3 and R.sub.4 are independently selected from hydrogen; loweralkyl of 1 to 4 carbon atoms; halo-substituted loweralkyl of 1 to 4 carbon atoms; arylalkyl of the formula ##STR4## wherein m is 0, 1 or 2, p is 0 or 1, R.sub.8 is hydrogen or loweralkyl of 1 to 4 carbon atoms and R.sub.9 and R.sub.10 are independently selected from hydrogen, hydroxy, methoxy, loweralkyl of 1 to 4 carbon atoms, or halo, or R.sub.9 and R.sub.10 can be taken together to form a methylenedioxy or ethylenedioxy bridge; or 1,4-benzodioxan of the formula ##STR5## wherein q is 1, 2 or 3, and R.sub.11 is hydrogen, methoxy, or halo; or R.sub.3 and R.sub.4 can be taken together to form a piperazino, piperidino or morpholino moiety; and the pharmaceutically acceptable salts thereof. Also disclosed are pharmaceutical compositions comprising compounds of formula (I) and a pharmaceutically acceptable carrier or diluent.

  本文揭示了由以下公式表示的1-氨甲基-邻苯二甲酰亚胺：##STR1##其中R，R.sub.1和R.sub.2独立地选自氢，羟基，1至3个碳原子的低烷氧基，1至3个碳原子的低烯氧基，硫甲基，卤素或##STR2##其中R.sub.5和R.sub.6独立地选自氢，1至4个碳原子的低酰基或式中的磺酰基##STR3##其中R.sub.7是1至4个碳原子的低烷基；或R和R.sub.1，或R.sub.1和R.sub.2可以结合成亚甲二氧或乙亚二氧桥；但必须至少有R，R.sub.1或R.sub.2中的一个不是氢；且R.sub.3和R.sub.4独立地选自氢；1至4个碳原子的低烷基；1至4个碳原子的卤代低烷基；式中的苯基烷基##STR4##其中m为0，1或2，p为0或1，R.sub.8为氢或1至4个碳原子的低烷基，R.sub.9和R.sub.10独立地选自氢，羟基，甲氧基，1至4个碳原子的低烷基或卤素，或R.sub.9和R.sub.10可以结合成亚甲二氧或乙亚二氧桥；或1,4-苯并二氧杂环的式子##STR5##其中q为1，2或3，R.sub.11为氢，甲氧基或卤素；或R.sub.3和R.sub.4可以结合成哌嗪，哌啶或吗啉基团；以及其药物可接受的盐。还揭示了包含式(I)化合物和药物可接受的载体或稀释剂的制药组合物。
• 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：——
• US4500543A
  申请人：——

  公开号：US4500543A

  公开（公告）日：1985-02-19
• 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.