2-benzyl-4-bromomethylpyridazin-3(2H)-one

• 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: 2-benzyl-4-bromomethylpyridazin-3(2H)-one
• 英文别名: 2-Benzyl-4-(bromomethyl)pyridazin-3-one；2-benzyl-4-(bromomethyl)pyridazin-3-one
• 化学式: C₁₂H₁₁BrN₂O
• 分子量: 279.136
• InChiKey: BLJPJHZPVVVYEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzyl-4-bromomethylpyridazin-3(2H)-one 在 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 2-benzyl-4-guanidinomethylpyridazin-3(2H)-one hydrochloride
  参考文献：
  名称：

  新型 Pyridazin-3(2H)-one-based 胍衍生物作为具有抗癌活性的潜在 DNA 小沟结合剂

  摘要：

  在分子对接研究的支持下，提出了含有 pyridazin-3(2 H )-one 核心的新型芳基胍类似物作为小沟粘合剂 (MGBs)。使用相应的甲硅烷基保护的哒嗪酮作为关键中间体，合成了在哒嗪酮部分不同位置显示胍基的目标双阳离子或单阳离子化合物。哒嗪酮支架被转化为足够的溴代烷基衍生物，通过与N , N' - di -Boc-保护的胍反应，然后酸水解，以良好的收率提供盐酸盐1-14。新哒哒嗪3( 2H )的能力)-one-based 胍作为 DNA 粘合剂通过 DNA 紫外热变性实验进行了研究。还在三种癌细胞系（NCI-H460、A2780 和 MCF-7）中探索了它们的抗增殖活性。具有双胍结构的化合物1-4显示出较弱的 DNA 结合亲和力，并在所研究的三种癌细胞系中表现出合理的细胞活力抑制百分比。

  DOI：

  10.1021/acsmedchemlett.1c00633
• 作为产物：
  描述：

  3-呋喃甲醇 在 咪唑 、 食用色素红色105号 、 四溴化碳 、 四丁基氟化铵 、 氧气 、 sodium hydride 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 56.0h， 生成 2-benzyl-4-bromomethylpyridazin-3(2H)-one
  参考文献：
  名称：

  New platelet aggregation inhibitors based on pyridazinone moiety

  摘要：

  New series of pyridazinone derivatives (4, 5 and 6) were synthesized in good yields following a synthetic strategy based on singlet oxygen oxidation of alkyl furans, in which a suitable beta(alpha)-substituted gamma-hydroxybutenolide (10 or 11) or a bicyclic lactone (12 or 13) was the key intermediate. The synthesized compounds were tested in vitro as antiplatelet agents and some of them (compounds 4b, 4d and 5b) exhibited potent inhibitory effects on collagen-induced platelet aggregation with IC50 values in the low mu M range. Studies performed with the most active compound of these series (4b) demonstrated its lack of activity as inhibitor of platelet aggregation induced by other agonists as thrombin, ionomycin or U-46619 suggesting a selective action on the biochemical mechanisms triggered by collagen in the platelets. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.061

文献信息

• Novel Pyridazin-3(2<i>H</i>)-one-Based Guanidine Derivatives as Potential DNA Minor Groove Binders with Anticancer Activity
  作者：María Carmen Costas-Lago、Noemí Vila、Adeyemi Rahman、Pedro Besada、Isabel Rozas、José Brea、María Isabel Loza、Elisa González-Romero、Carmen Terán

  DOI：10.1021/acsmedchemlett.1c00633

  日期：2022.3.10

  Novel aryl guanidinium analogues containing the pyridazin-3(2H)-one core were proposed as minor groove binders (MGBs) with the support of molecular docking studies. The target dicationic or monocationic compounds, which show the guanidium group at different positions of the pyridazinone moiety, were synthesized using the corresponding silyl-protected pyridazinones as key intermediates. Pyridazinone

  在分子对接研究的支持下，提出了含有 pyridazin-3(2 H )-one 核心的新型芳基胍类似物作为小沟粘合剂 (MGBs)。使用相应的甲硅烷基保护的哒嗪酮作为关键中间体，合成了在哒嗪酮部分不同位置显示胍基的目标双阳离子或单阳离子化合物。哒嗪酮支架被转化为足够的溴代烷基衍生物，通过与N , N' - di -Boc-保护的胍反应，然后酸水解，以良好的收率提供盐酸盐1-14。新哒哒嗪3( 2H )的能力)-one-based 胍作为 DNA 粘合剂通过 DNA 紫外热变性实验进行了研究。还在三种癌细胞系（NCI-H460、A2780 和 MCF-7）中探索了它们的抗增殖活性。具有双胍结构的化合物1-4显示出较弱的 DNA 结合亲和力，并在所研究的三种癌细胞系中表现出合理的细胞活力抑制百分比。
• New platelet aggregation inhibitors based on pyridazinone moiety
  作者：Tamara Costas、María Carmen Costas-Lago、Noemí Vila、Pedro Besada、Ernesto Cano、Carmen Terán

  DOI：10.1016/j.ejmech.2015.02.061

  日期：2015.4

  New series of pyridazinone derivatives (4, 5 and 6) were synthesized in good yields following a synthetic strategy based on singlet oxygen oxidation of alkyl furans, in which a suitable beta(alpha)-substituted gamma-hydroxybutenolide (10 or 11) or a bicyclic lactone (12 or 13) was the key intermediate. The synthesized compounds were tested in vitro as antiplatelet agents and some of them (compounds 4b, 4d and 5b) exhibited potent inhibitory effects on collagen-induced platelet aggregation with IC50 values in the low mu M range. Studies performed with the most active compound of these series (4b) demonstrated its lack of activity as inhibitor of platelet aggregation induced by other agonists as thrombin, ionomycin or U-46619 suggesting a selective action on the biochemical mechanisms triggered by collagen in the platelets. (C) 2015 Elsevier Masson SAS. All rights reserved.