4-chloro-5-(imidazol-1-yl)-2-nitroaniline | 131885-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-chloro-5-(imidazol-1-yl)-2-nitroaniline
• 英文别名: 4-Chloro-5-imidazol-1-yl-2-nitroaniline
• CAS: 131885-47-7
• 化学式: C₉H₇ClN₄O₂
• 分子量: 238.633
• InChiKey: YBTDCZJTADNAJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-5-(imidazol-1-yl)-2-nitroaniline 在 镍 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 4-Chloro-5-imidazol-1-ylbenzene-1,2-diamine
  参考文献：
  名称：

  Cardiotonic agents. Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles

  摘要：

  Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated. Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility. The structural features that impart optimal inotropic activity are presented. The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers. To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase. Two compounds, 1 and 4 1, showed interesting in vitro and oral activity without side effects. They have a more potent calcium-sensitizing effect than MCI-154 and are under futher investigation.

  DOI：

  10.1021/jm00101a024
• 作为产物：
  描述：

  咪唑 、 4,5-二氯-2-硝基苯胺 反应 24.0h， 生成 4-chloro-5-(imidazol-1-yl)-2-nitroaniline
  参考文献：
  名称：

  Cardiotonic agents. Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles

  摘要：

  Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated. Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility. The structural features that impart optimal inotropic activity are presented. The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers. To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase. Two compounds, 1 and 4 1, showed interesting in vitro and oral activity without side effects. They have a more potent calcium-sensitizing effect than MCI-154 and are under futher investigation.

  DOI：

  10.1021/jm00101a024

文献信息

• 7-Chloro-4,5-dihydro-8-(1,2,4-triazol-4-yl)- 4-oxo-1,2,4-triazolo[1,5-<i>a</i>]quinoxaline-2- carboxylates as Novel Highly Selective AMPA Receptor Antagonists
  作者：Daniela Catarzi、Vittoria Colotta、Flavia Varano、Lucia Cecchi、Guido Filacchioni、Alessandro Galli、Chiara Costagli、Vincenzo Carlà

  DOI：10.1021/jm0009686

  日期：2000.10.1
• Synthesis, Ionotropic Glutamate Receptor Binding Affinity, and Structure−Activity Relationships of a New Set of 4,5-Dihydro-8-heteroaryl-4-oxo-1,2,4-triazolo[1,5-<i>a</i>]quinoxaline-2-carboxylates Analogues of TQX-173
  作者：Daniela Catarzi、Vittoria Colotta、Flavia Varano、Guido Filacchioni、Alessandro Galli、Chiara Costagli、Vincenzo Carlà

  DOI：10.1021/jm010862q

  日期：2001.9.1

  A seires of 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates analogues of TQX-173 (1b), bearing different nitrogen-containing heterocycles at position-8, were synthesized as AMPA receptor antagonists. All the reported compounds were also biologically evaluated for their binding at glycine/NMDA and KA receptors to better assess their selectivity toward the AMPA receptor. Structure-activity relationships (SAR) on these TQX derivatives have evidenced that the precise positioning of the nitrogen atoms and the specific electronic topography of the 8-heteroaromatic ring are both important for the anchoring to the AMPA receptor. In fact, it has been well-established that the presence of a N-3-nitrogen-containing heterocycle at position-8 of the TQX framework is an essential feature for potent and selective AMPA receptor antagonists. Functional antagonism at both AMPA receptor and NMDA receptor-ion channel complex was evaluated by assessing the ability of some selected compounds to inhibit depolarization induced by 5 muM AMPA or NMDA in mouse cortical wedge preparations.
• Cardiotonic agents. Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles
  作者：Timur Gungor、Andre Fouquet、Jean Marie Teulon、Daniel Provost、Michele Cazes、Alix Cloarec

  DOI：10.1021/jm00101a024

  日期：1992.11

  Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated. Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility. The structural features that impart optimal inotropic activity are presented. The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers. To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase. Two compounds, 1 and 4 1, showed interesting in vitro and oral activity without side effects. They have a more potent calcium-sensitizing effect than MCI-154 and are under futher investigation.