ethyl 2-(3-methyl-6-oxo-5,6-dihydropyridazin-1(4H)-yl)acetate | 1065104-31-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(3-methyl-6-oxo-5,6-dihydropyridazin-1(4H)-yl)acetate
• 英文别名: ethyl 2-[3-methyl-6-oxo-5,6-dihydropyridazin-1(4H)-yl]acetate；ethyl 2-(3-methyl-6-oxo-4,5-dihydropyridazin-1-yl)acetate
• CAS: 1065104-31-5
• 化学式: C₉H₁₄N₂O₃
• mdl: MFCD11054384
• 分子量: 198.222
• InChiKey: OGAOTESPCKMISV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-methyl-6-oxo-5,6-dihydropyridazin-1(4H)-yl)acetate 在 盐酸 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 N'-(1-(4-methylphenyl)ethylidene)-2-(3-methyl-6-oxo-5,6-dihydropyridazin-1(4H)-yl)acetohydrazide
  参考文献：
  名称：

  Synthesis and antimycobacterial activities of some new N-acylhydrazone and thiosemicarbazide derivatives of 6-methyl-4,5-dihydropyridazin-3(2H)-one

  摘要：

  In this study, twenty-five new 6-methyl-4,5-dihydropyridazin-3(2H)-one derivatives having N-acylhydrazone and thiosemicarbazide moieties were synthesized. The target compounds were tested for their antimycobacterial activity in vitro against Mycobacterium tuberculosis H37Rv using the agar dilution method. Among the synthesized compounds, N'-(2,4-dichlorobenzylidene)-2-(3-methyl-6-oxo-5,6-dihydropyridazin-1(4H)-yl)acetohydrazide 4g was found to be the most active compound with minimum inhibitory concentration of 0.78 mu M and was more potent than ethambutol and ciprofloxacin.

  DOI：

  10.1007/s00044-011-9770-6
• 作为产物：
  描述：

  5-氧代己酸 在 potassium carbonate 、 一水合肼 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 ethyl 2-(3-methyl-6-oxo-5,6-dihydropyridazin-1(4H)-yl)acetate
  参考文献：
  名称：

  Synthesis and antimycobacterial activities of some new N-acylhydrazone and thiosemicarbazide derivatives of 6-methyl-4,5-dihydropyridazin-3(2H)-one

  摘要：

  In this study, twenty-five new 6-methyl-4,5-dihydropyridazin-3(2H)-one derivatives having N-acylhydrazone and thiosemicarbazide moieties were synthesized. The target compounds were tested for their antimycobacterial activity in vitro against Mycobacterium tuberculosis H37Rv using the agar dilution method. Among the synthesized compounds, N'-(2,4-dichlorobenzylidene)-2-(3-methyl-6-oxo-5,6-dihydropyridazin-1(4H)-yl)acetohydrazide 4g was found to be the most active compound with minimum inhibitory concentration of 0.78 mu M and was more potent than ethambutol and ciprofloxacin.

  DOI：

  10.1007/s00044-011-9770-6

文献信息

• Further studies on 2-arylacetamide pyridazin-3(2H)-ones: Design, synthesis and evaluation of 4,6-disubstituted analogs as formyl peptide receptors (FPRs) agonists
  作者：Maria Paola Giovannoni、Igor A. Schepetkin、Agostino Cilibrizzi、Letizia Crocetti、Andrei I. Khlebnikov、Claes Dahlgren、Alessia Graziano、Vittorio Dal Piaz、Liliya N. Kirpotina、Serena Zerbinati、Claudia Vergelli、Mark T. Quinn

  DOI：10.1016/j.ejmech.2013.03.066

  日期：2013.6

  Formyl peptide receptors (FPRs) play an essential role in the regulation of endogenous inflammation and immunity. In the present studies, a large series of pyridazin-3(2H)-one derivatives bearing an arylacetamide chain at position 2 was synthesized and tested for FPR agonist activity. The pyridazin-3(2H)-one ring was confirmed to be an appropriate scaffold to support FPR agonist activity, and its modification

  甲酰肽受体 (FPR) 在调节内源性炎症和免疫中起重要作用。在本研究中，合成了大量在 2 位带有芳基乙酰胺链的哒嗪-3(2 H )-one 衍生物并测试了 FPR 激动剂活性。哒嗪-3(2 H )-one 环被证实是支持 FPR 激动剂活性的合适支架，其在 4 和 6 位的修饰导致鉴定出额外的活性激动剂，从而诱导细胞内 Ca 2+在HL-60 细胞转染了 FPR1、FPR2 或 FPR3。七种甲酰肽受体 1 (FPR1) 特异性和几种混合的 FPR1/FPR2 双激动剂被鉴定为低微摩尔 EC 50值。此外，这些激动剂还激活人类中性粒细胞，诱导细胞内 Ca 2+通量和趋化性。最后，分子对接研究表明，最有效的哒嗪-3(2 H )-ones 分别在 FPR1 和 FPR2 配体结合位点与 fMLF 和 WKYMVM 肽的最佳对接姿势重叠。因此，哒嗪酮类化合物代表了用于进一步开发选择性和/或有效 FPR