4,5-diiodo-2-phenylpyridazin-3(2H)-one | 21235-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4,5-diiodo-2-phenylpyridazin-3(2H)-one
• CAS: 21235-51-8
• 化学式: C₁₀H₆I₂N₂O
• 分子量: 423.979
• InChiKey: RILMDNPLOQDABP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,5-diiodo-2-phenylpyridazin-3(2H)-one 在 sodium azide 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.58h， 生成 5-(4-acetyl-5-methyl-1H-1,2,3-triazol-1-yl)-4-iodo-2-phenylpyridazin-3(2H)-one
  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
• 作为产物：
  描述：

  4,5-diiodopyridazin-3(2H)-one 、 苯硼酸 在 吡啶 、 2,2,6,6-四甲基哌啶氧化物 、 copper(II) acetate monohydrate 作用下， 以 二氯甲烷 为溶剂， 反应 216.0h， 以28%的产率得到4,5-diiodo-2-phenylpyridazin-3(2H)-one
  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

• 2-Substituted 4-, 5-, and 6-[(1E)-3-oxo-3-phenylprop-1-en-1-yl]pyridazin-3(2H)-ones and 2-substituted 4,5-bis[(1E)-3-oxo-3-phenylprop-1-en-1-yl]pyridazin-3(2H)-ones as potent platelet aggregation inhibitors: Design, synthesis, and SAR studies
  作者：Caroline Meyers、Matilde Yáñez、Abdelaziz Elmaatougi、Tom Verhelst、Alberto Coelho、Nuria Fraiz、Guy L.F. Lemière、Xerardo Garcı´a-Mera、Reyes Laguna、Ernesto Cano、Bert U.W. Maes、Eddy Sotelo

  DOI：10.1016/j.bmcl.2007.11.034

  日期：2008.1

  regioisomeric 2-substituted pyridazin-3(2H)-ones containing a 3-oxo-3-phenylprop-1-en-1-yl fragment at either position 4, 5 or 6 and 2-substituted pyridazin-3(2H)-ones containing the same fragment both at positions 4 and 5 have been synthesized and evaluated as antiplatelet agents. The study allows the identification of a new highly potent platelet aggregation inhibitor (4c).

  一组区域异构的2-取代的哒嗪-3（2H）-在4、5或6位上含有3-氧代-3-苯基丙-1-烯-1-基片段和2-取代的哒嗪-3（2H） ）-已经合成了在4和5位都含有相同片段的β-内酯，并将其评估为抗血小板剂。该研究可以鉴定出一种新型的高效血小板凝集抑制剂（4c）。