8-Acetyl-6,7,8,9-tetrahydro<1,2,3>thiadiazolo<5,4-h>isoquinoline | 78104-37-7

• 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: 8-Acetyl-6,7,8,9-tetrahydro<1,2,3>thiadiazolo<5,4-h>isoquinoline
• 英文别名: 1-(7,9-dihydro-6H-thiadiazolo[5,4-h]isoquinolin-8-yl)ethanone
• CAS: 78104-37-7
• 化学式: C₁₁H₁₁N₃OS
• 分子量: 233.294
• InChiKey: ZDAZBFYZFHEEPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-Acetyl-6,7,8,9-tetrahydro<1,2,3>thiadiazolo<5,4-h>isoquinoline 生成 6,7,8,9-Tetrahydro-3-thia-1,2,8-triaza-cyclopenta[a]naphthalene; hydrochloride
  参考文献：
  名称：

  BONDINELL, W. E.;DEMARINIS, R. M.;HIEBLE, J. P.;PENDLETON, R. G.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Acetyl-8-amino-7-(benzylthio)-1,2,3,4-tetrahydroisoquinoline 在 盐酸 、 溶剂黄146 、 copper(l) chloride 、 sodium nitrite 作用下， 反应 8.08h， 生成 8-Acetyl-6,7,8,9-tetrahydro<1,2,3>thiadiazolo<5,4-h>isoquinoline
  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