5-叠氮基-4-氯-2-苯基哒嗪-3-酮 | 1503-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-叠氮基-4-氯-2-苯基哒嗪-3-酮
• 英文名称: 5-azido-4-chloro-2-phenylpyridazin-3(2H)-one
• 英文别名: 5-Azido-4-chloro-2-phenylpyridazin-3-one
• CAS: 1503-68-0
• 化学式: C₁₀H₆ClN₅O
• 分子量: 247.644
• InChiKey: PXDKCEJJDZPWLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-叠氮基-4-氯-2-苯基哒嗪-3-酮 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 N-isobutyl-5-(4-methoxybenzyl)-4,6-dioxo-7-phenyl-4,5,6,7-tetrahydro-[1,2,3]triazolo[1',5':1,6]pyrazino[2,3-d]pyridazine-3-carboxamide
  参考文献：
  名称：

  One-pot synthesis of [1,2,3]triazole-fused pyrazinopyridazindione tricycles by a ‘click and activate’ approach

  摘要：

  Substituted [1,2,3]triazole-fused pyrazinopyridazindione tricycles were synthesized in a four-component, stepwise condensation. The key step in this one-pot process was a thermal [3+2] triazole formation which activated the adjacent position and set the stage for a subsequent tandem nucleophilic aromatic substitution/cyclization sequence. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2011.11.030
• 作为产物：
  描述：

  5-溴-4-氯-2-苯基哒嗪-3(2H)-酮 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到5-叠氮基-4-氯-2-苯基哒嗪-3-酮
  参考文献：
  名称：

  Targeting the Warburg Effect in cancer; relationships for 2-arylpyridazinones as inhibitors of the key glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3)

  摘要：

  High-throughput screening of a small-molecule library identified a 5-triazolo-2-arylpyridazinone as a novel inhibitor of the important glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3). Such inhibitors are of interest due to PFKFB3's control of the important glycolytic pathway used by cancer cells to generate ATP. A series of analogues was synthesized to study structure-activity relationships key to enzyme inhibition. Changes to the triazolo or pyridazinone rings were not favoured, but limited-size substitutions on the aryl ring provided modest increases in potency against the enzyme. Selected analogues and literature-described inhibitors were evaluated for their ability to suppress the glycolytic pathway, as detected by a decrease in lactate production, but none of these compounds demonstrated such suppression at non-cytotoxic concentrations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.041

文献信息

• A “Click and Activate” Approach in One-Pot Synthesis of a Triazolyl-Pyridazinone Library
  作者：Wenyuan Qian、David Winternheimer、Jennifer Allen

  DOI：10.1021/ol200183b

  日期：2011.4.1

  A "click and activate" strategy was designed and executed in a four-component, stepwise condensation that led to a trisubstituted triazolyl-pyridazinone library. This one-pot process included regioselective azide substitution at 2-substituted-4,5-dichloropyridazinones, followed by a Cu(l) catalyzed triazole formation which triggered subsequent nucleophilic substitution at the neighboring position to achieve three points of diversity.
• Efficient N-arylation of pyridazin-3(2H)-ones
  作者：Jeum-Jong Kim、Yong-Dae Park、Su-Dong Cho、Ho-Kyun Kim、Hyun A. Chung、Sang-Gyeong Lee、J.R. Falck、Yong-Jin Yoon

  DOI：10.1016/j.tetlet.2004.10.003

  日期：2004.11

  A variety of substituted pyridazin-3(2H)-ones are directly N-arylated in good yield using lead tetraacetate/zinc chloride in benzene or in substituted benzenes including chloro- and bromobenzene. (C) 2004 Elsevier Ltd. All rights reserved.
• Targeting the Warburg Effect in cancer; relationships for 2-arylpyridazinones as inhibitors of the key glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3)
  作者：Darby G. Brooke、Ellen M. van Dam、Colin K.W. Watts、Amanda Khoury、Marie A. Dziadek、Hilary Brooks、Lisa-Jane K. Graham、Jack U. Flanagan、William A. Denny

  DOI：10.1016/j.bmc.2013.12.041

  日期：2014.2

  High-throughput screening of a small-molecule library identified a 5-triazolo-2-arylpyridazinone as a novel inhibitor of the important glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3). Such inhibitors are of interest due to PFKFB3's control of the important glycolytic pathway used by cancer cells to generate ATP. A series of analogues was synthesized to study structure-activity relationships key to enzyme inhibition. Changes to the triazolo or pyridazinone rings were not favoured, but limited-size substitutions on the aryl ring provided modest increases in potency against the enzyme. Selected analogues and literature-described inhibitors were evaluated for their ability to suppress the glycolytic pathway, as detected by a decrease in lactate production, but none of these compounds demonstrated such suppression at non-cytotoxic concentrations. (C) 2013 Elsevier Ltd. All rights reserved.
• One-pot synthesis of [1,2,3]triazole-fused pyrazinopyridazindione tricycles by a ‘click and activate’ approach
  作者：Wenyuan Qian、David Winternheimer、Albert Amegadzie、Jennifer Allen

  DOI：10.1016/j.tetlet.2011.11.030

  日期：2012.1

  Substituted [1,2,3]triazole-fused pyrazinopyridazindione tricycles were synthesized in a four-component, stepwise condensation. The key step in this one-pot process was a thermal [3+2] triazole formation which activated the adjacent position and set the stage for a subsequent tandem nucleophilic aromatic substitution/cyclization sequence. (C) 2011 Published by Elsevier Ltd.