1-(aminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride hemihydrate | 60085-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-(aminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride hemihydrate
• 英文别名: 1-aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride；1-(aminomethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrochloride
• CAS: 60085-38-3
• 化学式: C₁₀H₁₄N₂O₂*2ClH
• 分子量: 267.155
• InChiKey: ZQBWUIXFFRGQQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  78.51
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-(aminomethyl)-2-benzyl-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroisoquinoline 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 生成 1-(aminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride hemihydrate
  参考文献：
  名称：

  Synthesis of 1-(aminomethyl)-1,2,3,4-tetrahydroisoquinolines and their actions at adrenoceptors in vivo and in vitro

  摘要：

  An improved synthesis of 1-(aminomethyl)-1,2,3,4-tetrahydroisoquinolines has been developed by using aluminum hydride reduction of 1-cyano-1,2,3,4-tetrahydroisoquinolines. Three 1-(aminomethyl)-6,7-dihydroxytetrahydroisoquinolines were tested for actions at beta adrenoceptors in order to examine a proposed similarity between this series and the related phenylethanolamines. The aminomethyl, (isopropylamino)methyl, and (tert-butylamino)methyl derivatives all showed weak partial agonist activity at beta adrenoceptors and the first also showed weak alpha adrenoceptor agonist activity in vivo. Their low potency implies that the catechol group of THIQ sympathomimetics, such as trimetoquinol, binds differently from that of the natural catecholamines. The protonation behavior of representative aminomethyl-THIQ's was investigated by pKa measurement and 1H and 13C NMR, and the compounds were shown to be substantially monoprotonated, on the exocyclic nitrogen, at physiological pH.

  DOI：

  10.1021/jm00358a010

文献信息

• 1,2,3,4-Tetrahydroisoquinolines and the preparation thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04220647A1

  公开（公告）日：1980-09-02

  1,2,3,4-tetrahydroisoquinolines have the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen, lower alkyl, lower alkenyl, acyl, aryl or ar(lower)alkyl, in which aryl and the aryl moiety of the ar(lower)alkyl may contain at least one substituent selected from the group consisting of halogen, lower alkoxy, amino, nitro, hydroxy, acyloxy, ar(lower)alkoxy, lower alkylenedioxy, halo(lower)alkyl, acylamino, ar(lower)alkylamino and aryl, and pharmaceutically acceptable salts thereof.

  1,2,3,4-四氢异喹啉的化学式为：##STR1## 其中 R.sub.1 和 R.sub.2 分别为氢、较低的烷基、较低的烯基、酰基、芳基或芳基-(较低)烷基，其中芳基和芳基-(较低)烷基可能含有至少一种取代基，所选取代基包括卤素、较低的烷氧基、氨基、硝基、羟基、酰氧基、芳基-(较低)烷氧基、较低的烷基二氧基、卤代(较低)烷基、酰胺基、芳基-(较低)烷基胺基和芳基，以及其药用可接受的盐。