8-硝基-5-异喹啉胺 | 156901-58-5

• 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: 8-硝基-5-异喹啉胺
• 英文名称: 5-amino-8-nitroisoquinoline
• 英文别名: 8-Nitroisoquinolin-5-amine
• CAS: 156901-58-5
• 化学式: C₉H₇N₃O₂
• mdl: MFCD00837756
• 分子量: 189.173
• InChiKey: QKGFZLNYZKMJBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  260-268 °C (decomp)
• 沸点：
  459.6±35.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  8-硝基-5-异喹啉胺 在 盐酸 、 sodium nitrite 、 亚膦酸 作用下， 反应 12.0h， 以49%的产率得到5-hydroxyisoquinoline
  参考文献：
  名称：

  Synthesis and Flow Cytometric Evaluation of Novel 1,2,3,4-Tetrahydroisoquinoline Conformationally Constrained Analogues of Nitrobenzylmercaptopurine Riboside (NBMPR) Designed for Probing Its Conformation When Bound to the es Nucleoside Transporter

  摘要：

  Novel regioisomers of conformationally constrained analogues of the potent es nucleoside transporter ligand, nitrobenzylmercaptopurine riboside (NBMPR), designed for probing its bound (bioactive) conformation, were synthesized and evaluated as es transporter ligands by flow cytometry. Purine 6-position 5, 6, 7, or 8-nitro-1,2,3,4-tetrahydroisoquinolylpurine ribosides, in which the nitrobenzyl moiety in NBMPR has been locked into the nitro-1,2,3,4-tetrahydroisoquinoline system, were synthesized by reaction of the appropriate nitro-1,2,3,4-tetrahydroisoquinoline with 6-chloropurine riboside. Flow cytometry was performed using 5-(SAENTA)X8-fluorescein as the competitive ligand. A high degree of variation in the es transporter binding capacity of the target compounds was observed, with the K-i values ranging from 0.45 nM for the most tightly bound compound (4) to 300 nM for the least tightly bound compound (5). The Ki of NBMPR was 0.70 nM, a little higher than that of compound 4. Compound 4 is the isomer that has the nitro group in the best orientation at the es transporter binding site compared to the other three compounds, 2, 3, and 5.

  DOI：

  10.1021/jm020405p
• 作为产物：
  描述：

  5-氨基异喹啉 在 盐酸 、 硫酸 、 potassium nitrate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.08h， 生成 8-硝基-5-异喹啉胺
  参考文献：
  名称：

  Synthesis and Flow Cytometric Evaluation of Novel 1,2,3,4-Tetrahydroisoquinoline Conformationally Constrained Analogues of Nitrobenzylmercaptopurine Riboside (NBMPR) Designed for Probing Its Conformation When Bound to the es Nucleoside Transporter

  摘要：

  Novel regioisomers of conformationally constrained analogues of the potent es nucleoside transporter ligand, nitrobenzylmercaptopurine riboside (NBMPR), designed for probing its bound (bioactive) conformation, were synthesized and evaluated as es transporter ligands by flow cytometry. Purine 6-position 5, 6, 7, or 8-nitro-1,2,3,4-tetrahydroisoquinolylpurine ribosides, in which the nitrobenzyl moiety in NBMPR has been locked into the nitro-1,2,3,4-tetrahydroisoquinoline system, were synthesized by reaction of the appropriate nitro-1,2,3,4-tetrahydroisoquinoline with 6-chloropurine riboside. Flow cytometry was performed using 5-(SAENTA)X8-fluorescein as the competitive ligand. A high degree of variation in the es transporter binding capacity of the target compounds was observed, with the K-i values ranging from 0.45 nM for the most tightly bound compound (4) to 300 nM for the least tightly bound compound (5). The Ki of NBMPR was 0.70 nM, a little higher than that of compound 4. Compound 4 is the isomer that has the nitro group in the best orientation at the es transporter binding site compared to the other three compounds, 2, 3, and 5.

  DOI：

  10.1021/jm020405p

文献信息

• Deamination of 5-Amino-8-nitroisoquinoline¹
  作者：Bertram Keilin、W. E. Cass

  DOI：10.1021/ja01262a062

  日期：1942.10
• Wozniak, Marian; Nowak, Krystyna, Liebigs Annalen der Chemie, 1994, # 4, p. 355 - 360
  作者：Wozniak, Marian、Nowak, Krystyna

  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：——