2,3-Dihydro-2-oxo-6,7,8,9-tetrahydroimidazo[4,5-h]isoquinoline Hydrochloride | 120546-65-8

• 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: 2,3-Dihydro-2-oxo-6,7,8,9-tetrahydroimidazo[4,5-h]isoquinoline Hydrochloride
• 英文别名: 1,3,6,7,8,9-Hexahydroimidazo[4,5-h]isoquinolin-2-one;hydrochloride
• CAS: 120546-65-8
• 化学式: C₁₀H₁₁N₃O*ClH
• 分子量: 225.678
• InChiKey: JJEAYRBOEGKDNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  53.2
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7,8-异喹啉二胺 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 170.0~180.0 ℃ 、413.69 kPa 条件下， 反应 3.0h， 生成 2,3-Dihydro-2-oxo-6,7,8,9-tetrahydroimidazo[4,5-h]isoquinoline Hydrochloride
  参考文献：
  名称：

  Tetrahydro thiadiazolo isoquinolines: synthesis and inhibition of phenylethanolamine-N-methyltransferase

  摘要：

  A series of 7,8-fused heterocyclic tetrahydroisoquinolines were synthesized and tested as inhibitors of rabbit adrenal phenylethanolamine-N-methyltransferase (PNMT). 6,7,8,9-Tetrahydro[1,2,3]thiadiazolo[5,4-h]isoquinoline 5 (SK&F 86607) was found to be a potent inhibitor of PNMT with an IC50 similar to that of 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline (1, SK&F 64139). The isomeric tetrahydro[1,2,3]thiadiazolo[4,5-h]- and tetrahydro[1,2,5]thiadiazolo[3,4-h]isoquinolines, 13 and 20, were also potent PNMT inhibitors. However, substitution of Cl at position 5 (17) resulted in loss of potency similar to the loss observed in the 5-chloro analogue of 1. The 1,2,5 isomer 20 showed only a small drop in activity at 10(-6) M. All of the thiadiazoles were more potent than the 7,8-benzo-fused analogue 36. Fusion of other five-membered heterocyclic ring systems at the 7,8-position, e.g. triazole 22 and imidazoles 24 and 26, resulted in a decrease of PNMT inhibition. The alpha-adrenoreceptor affinities of 1 and 5 were also compared.

  DOI：

  10.1021/jm00127a027

文献信息

• Tetrahydro thiadiazolo isoquinolines: synthesis and inhibition of phenylethanolamine-N-methyltransferase
  作者：Gerald R. Girard、William E. Bondinell、Leonard M. Hillegass、Kenneth G. Holden、Robert G. Pendleton、Irene Uzinskas

  DOI：10.1021/jm00127a027

  日期：1989.7

  A series of 7,8-fused heterocyclic tetrahydroisoquinolines were synthesized and tested as inhibitors of rabbit adrenal phenylethanolamine-N-methyltransferase (PNMT). 6,7,8,9-Tetrahydro[1,2,3]thiadiazolo[5,4-h]isoquinoline 5 (SK&F 86607) was found to be a potent inhibitor of PNMT with an IC50 similar to that of 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline (1, SK&F 64139). The isomeric tetrahydro[1,2,3]thiadiazolo[4,5-h]- and tetrahydro[1,2,5]thiadiazolo[3,4-h]isoquinolines, 13 and 20, were also potent PNMT inhibitors. However, substitution of Cl at position 5 (17) resulted in loss of potency similar to the loss observed in the 5-chloro analogue of 1. The 1,2,5 isomer 20 showed only a small drop in activity at 10(-6) M. All of the thiadiazoles were more potent than the 7,8-benzo-fused analogue 36. Fusion of other five-membered heterocyclic ring systems at the 7,8-position, e.g. triazole 22 and imidazoles 24 and 26, resulted in a decrease of PNMT inhibition. The alpha-adrenoreceptor affinities of 1 and 5 were also compared.