7-氨基-8-亚硝基异喹啉 | 56623-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 7-氨基-8-亚硝基异喹啉
• 英文名称: 7-amino-8-nitrosoisoquinoline
• 英文别名: 7-Amino-8-nitroisoquinoline；8-nitro-[7]isoquinolylamine；8-Nitro-[7]isochinolylamin；7-Amino-8-nitro-isochinolin；8-Nitroisoquinolin-7-amine
• CAS: 56623-94-0
• 化学式: C₉H₇N₃O₂
• 分子量: 189.173
• InChiKey: KWUPGPORZRLDHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-氨基-8-亚硝基异喹啉 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 反应 1.0h， 生成 Imidazo<4,5-h>isoquinoline Dihydrochloride
  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
• 作为产物：
  描述：

  7-氯异喹啉 在 硫酸 、 氨 、 potassium nitrate 作用下， 生成 7-氨基-8-亚硝基异喹啉
  参考文献：
  名称：

  Manske; Kulka, Canadian Journal of Research, Section B: Chemical Sciences, 1949, vol. 27, p. 161,166

  摘要：

  DOI：

文献信息

• WOZNIAK, MARIAN;BARANSKI, ANDRZEJ;NOWAK, KRYSTYNA;PORADOWSKA, HENRYKA, LIEBIGS ANN. CHEM.,(1990) N, C. 653-657
  作者：WOZNIAK, MARIAN、BARANSKI, ANDRZEJ、NOWAK, KRYSTYNA、PORADOWSKA, HENRYKA

  DOI：——

  日期：——
• 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：——
• LEBENSTEDT E.; SCHUNACK W., ARCH. PHARM. <APBD-AJ>, 1975, 308, NO 6, 413-417
  作者：LEBENSTEDT E.、 SCHUNACK W.

  DOI：——

  日期：——
• Manske; Kulka, Canadian Journal of Research, Section B: Chemical Sciences, 1949, vol. 27, p. 161,166
  作者：Manske、Kulka

  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.