(9CI)-6,7,8,9-四氢-噻唑并[4,5-h]异喹啉 | 120546-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: (9CI)-6,7,8,9-四氢-噻唑并[4,5-h]异喹啉
• 中文别名: (9CI)-6,7,8,9-四氢-噻唑并[4,5-H]异喹啉
• 英文名称: 1,2,3,4-Tetrahydrothiazolo[4,5-h]isoquinoline
• 英文别名: 6,7,8,9-Tetrahydrothiazolo[4,5-h]isoquinoline；6,7,8,9-tetrahydro-[1,3]thiazolo[4,5-h]isoquinoline
• CAS: 120546-67-0
• 化学式: C₁₀H₁₀N₂S
• 分子量: 190.269
• InChiKey: SOJYQCQXDKHYPT-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  355.7±32.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 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：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯-6,7,8,9-四氢[1,3]噻唑并[4,5-h]异喹啉 在 磷化氢 、 氢碘酸 、 溶剂黄146 作用下， 反应 3.0h， 以42%的产率得到(9CI)-6,7,8,9-四氢-噻唑并[4,5-h]异喹啉
  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

• GIRARD, GERALD R.;BONDINELL, WILLIAM E.;HILLEGASS, LEONARD M.;HOLDEN, KEN+, J. MED. CHEM. , 32,(1989) N, C. 1566-1571
  作者：GIRARD, GERALD R.、BONDINELL, WILLIAM E.、HILLEGASS, LEONARD M.、HOLDEN, KEN+

  DOI：——

  日期：——
• 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.