9-nitrobenzoquinolizinium perchlorate | 27755-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 9-nitrobenzoquinolizinium perchlorate
• 英文别名: 9-mitrobenzo[b]quinolizinium perchlorate；9-nitrobenzo[b]quinolizinium perchlorate；9-Nitropyrido[1,2-b]isoquinolin-5-ium perchlorate；9-nitrobenzo[b]quinolizin-5-ium;perchlorate
• CAS: 27755-38-0
• 化学式: C₁₃H₉N₂O₂*ClO₄
• 分子量: 324.677
• InChiKey: WWSLDIWTCMIWEQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.27
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-nitrobenzoquinolizinium perchlorate 在 nitroreductase from Escherichia coli 、 还原型辅酶Ⅰ 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.67h， 生成 9-aminoacridizinium cation
  参考文献：
  名称：

  9-Nitrobenzo[b]quinolizinium 作为荧光探针用于体外和大肠杆菌中检测硝基还原酶

  摘要：

  无荧光的 9-硝基苯并[ b ]喹啉鎓很容易被硝基还原酶还原成荧光反应产物。由此产生的点亮效应能够在体外和大肠杆菌细菌培养物中选择性检测硝基还原酶活性。

  DOI：

  10.1039/d1nj05230f

文献信息

• Identification, Synthesis, and Characterization of a Unique Class of N-Methyl-D-aspartate Antagonists. The 6,11-Ethanobenzo[b]quinolizinium Cation
  作者：John P. Mallamo、William G. Earley、Virendra Kumar、Chakrapani Subramanyam、John A. Jr. Dority、Matthew S. Miller、Diane L. DeHaven-Hudkins、Brian Ault、John L. Herrmann

  DOI：10.1021/jm00052a003

  日期：1994.12

  A series of novel N-methyl-D-aspartate antagonists acting at the phencyclidine site has been identified. Compound 2 has a Ki = 8 +/- 1 nM (vs [3H]thienylcyclidine, [3H]TCP) as a mixture of enantiomers. Resolution and further testing indicate that (-)-2, Ki = 4 +/- 0.7 nM, is a potent and selective TCP site ligand with neuroprotective activity in cultured neurons in the presence of excitotoxic concentrations

  已经鉴定了一系列作用于苯环利定位点的新型N-甲基-D-天冬氨酸拮抗剂。化合物2具有Ki ＝ 8 +/- 1nM（相对于[3H]噻吩基环啶，[3H] TCP）对映异构体的混合物。分辨率和进一步测试表明，（-）-2（Ki = 4 +/- 0.7 nM）是一种有效且选择性的TCP位点配体，在存在兴奋毒性浓度的NMDA（IC50 = 26 nM）的情况下，对培养的神经元具有神经保护活性。相对于包括鸦片，肾上腺素，5-羟色胺能，多巴胺，腺苷，二氢吡啶和苯并二氮杂a在内的一系列受体类型，化合物（-）-2对TCP位置的选择性> 1000倍，并且对活化的（开放的）NMDA受体具有更高的选择性。离子通道复合物与PCP和MK801的关系，可通过培养的电压钳制神经元中的贴片记录进行测量。高度增强的“开放渠道” 选择性导致这些配体的初步分类为与NMDA不竞争。具有这些特征的配体可以使与典型的非竞争性NMDA拮抗剂
• Substituted 6,11-ethano-6,11-dihydrobenzo[b]quinolizinium salts and compositionsand methods of use thereof
  申请人：STERLING WINTHROP INC.

  公开号：EP0656359A1

  公开（公告）日：1995-06-07

  Substituted 6,11-ethano-6,11-dihydrobenzo[b]quinolizinium salts of Formula, pharmaceutical compositions containing them, and methods for the treatment or prevention of neurodegenerative disorders or neurotoxic injuries utilizing them.

  式中的取代的 6,11-乙hano-6,11-二氢苯并[b]喹嗪盐、 含有它们的药物组合物，以及利用它们治疗或预防神经退行性疾病或神经毒性损伤的方法。
• 12-Hetero-substituted 6,11-ethano-6,11-dihydrobenzo[b] quinolizium salts and compositions and method of use thereof
  申请人：STERLING WINTHROP INC.

  公开号：EP0648769A1

  公开（公告）日：1995-04-19

  12-Hetero substituted 6,11-ethano-6,11-dihydrobenzo[b]quinolizinium salts, pharmaceutical compositions containing them, and methods for the treatment or prevention of neurodegenerative disorders or neurotoxic injuries utilizing them.

  12-杂取代的 6,11-乙hano-6,11-dihydrobenzo[b]quinolizinium 盐、含有它们的药物组合物，以及利用它们治疗或预防神经退行性疾病或神经毒性损伤的方法。
• Synthesis and Evaluation of 6,11-Ethanohexahydrobenzo[b]quinolizidines: A New Class of Noncompetitive N-Methyl-D-aspartate Antagonists
  作者：Chakrapani Subramanyam、John P. Mallamo、Gary M. Pilling、William G. Earley、Philip M. Carabateas、Joseph R. Wetzel、Diane DeHaven-Hudkins、Timothy Allen、Rudolph K. Kullnig

  DOI：10.1021/jm00013a025

  日期：1995.6

  The synthesis and in vitro and in vivo evaluation of 12,13-cycloalkyl-6,11-ethanobenzo[b]quinolizidines, a new class of noncompetitive N-methyl-D-aspartate (NMDA) antagonists acting at the PCP site on the NMDA receptor complex, is reported. Structure-activity relationship studies led to the identification of 10-hydroxy-(6 alpha,11 alpha,11 alpha beta,12R*,13S*)-1,15,16-decahydro-12H-6,11[1',2']-endo-cyclopenta-2H-pyrido[1,2-b]isoquinoline hydrobromide (5h) and 9-hydroxy-(6 alpha,11 alpha,11 alpha beta,12R*,13S*)-1,3,4,6,11,11a,13,14,15,16-decahydro-12H-6,11[1',2']-endo-cyclopenta-2H-pyrido[1,2-b]isoquinoline hydrobromide(5i), the most potent members of this series with K-i values of 2.3 +/- 0.2 and 2.3 +/- 0.5 nM, respectively. Molecular modeling studies revealed that this series of compounds occupies both lipophilic sites of the Andrews PCP receptor model and shares structural features which are common to other classes of known noncompetitive NMDA antagonists such as MK-801.
• US5380729A
  申请人：——

  公开号：US5380729A

  公开（公告）日：1995-01-10