(E)-N-(4-methoxybenzylidene)-N'-(2-pyridyl)hydrazine | 560101-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-N-(4-methoxybenzylidene)-N'-(2-pyridyl)hydrazine
• 英文别名: (E)-p-methoxybenzaldehyde 2-pyridylhydrazone；N-[(E)-(4-methoxyphenyl)methylideneamino]pyridin-2-amine
• CAS: 560101-31-7
• 化学式: C₁₃H₁₃N₃O
• 分子量: 227.266
• InChiKey: HIKHVXGHZYHVJA-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N-(4-methoxybenzylidene)-N'-(2-pyridyl)hydrazine 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以82%的产率得到3-(4-(methyloxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridine
  参考文献：
  名称：

  高价碘介导的1-芳基/ hetryl-1,2,4-三唑[4,3-a]吡啶和1-芳基/ hetryl 5-甲基-1,2,4-三唑[4,3-a]的合成喹啉作为抗菌剂。

  摘要：

  用二氯甲烷中的碘代二苯乙酸酯（IBD）氧化2-吡啶基和2-喹啉yl，生成1-芳基/ hetryl-1,2,4-trizolo- [4,3-a]吡啶（3a-f）和1-芳基/ hetryl-5-甲基-1,2,4-三唑并[4,3-a]喹啉（6a-f）。体外测试了七种化合物的抗菌活性。1-（5'-硝基-2-呋喃基）-5-甲基-1,2,4-三唑并[4,3-a]喹啉（6e）的抗菌活性明显高于某些商业上针对鼠伤寒沙门氏菌的抗生素。 MIC，即10微克mL（-1）。

  DOI：

  10.1016/s0223-5234(03)00061-8
• 作为产物：
  描述：

  2-溴吡啶 在 盐酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 (E)-N-(4-methoxybenzylidene)-N'-(2-pyridyl)hydrazine
  参考文献：
  名称：

  Synthesis and evaluation of analgesic, antiinflammatory and antiplatelet properties of new 2-pyridylarylhydrazone derivatives

  摘要：

  This work describes recent results from our research program aiming at the synthesis and pharmacological evaluation of new compounds acting as antiinflammatory, analgesic and platelet antiaggregatory. In this paper the synthesis and the pharmacological profile as analgesic, antiinflammatory and anti-platelet of new functionalized 2-pyridylarylhydrazone derivatives 5a-r are discussed. This class of N-heterocyclic derivatives represents a new series of prototype candidates with analgesic and antiinflammatory properties possessing also an important anti-aggregating activity. The pharmacological results herein disclosed suggest that the antiinflammatory and analgesic activities of these new pyridynehydrazone derivatives observed in the carrageenan pleurisy model and acetic acid writhing test, respectively is probably due to an interference on the arachidonic acid (AA) metabolism. The most important antiinflammatory derivative 2-(2-formylfurane)pyridylhydrazone 5p presented a 79% inhibition of pleurisy at a dose of 80.1 mu mol/kg. We also described the results concerning the mechanism of action of this series of N-heterocyclic derivatives in platelet aggregation which suggest a Ca2+ participation, probably by a complexation scavenger mechanism. Compound 2-(2-formylfurane)pyridylhydrazone 5p was able to complex Ca2+ in in vitro experiments at 100 mu M concentration, indicating that this series of compounds can act as Ca2+ scavenger depending on the nature of the aryl moiety present at the imine subunit. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80008-1

文献信息

• <i>N</i>-(4-Methoxybenzylidene)-<i>N</i>′-(2-pyridyl)hydrazine
  作者：Tuncay Tunc˛、Musa Sarı、Rahmi Yagbasan、Habibe Tezcan、Ertan S˛ahin

  DOI：10.1107/s0108270103004256

  日期：2003.4.15

  Molecules of the title compound (alternative name p-methoxybenzaldehyde 2-pyridylhydrazone), C13H13N3O, adopt an E configuration about the azomethine C=N double bond. Molecules are almost planar, the dihedral angle between the pyridine and methoxyphenyl rings being only 6.19 (12)degrees. Pairwise N-H...N hydrogen bonds [R-2(2)(8) in graph-set notation] link centrosymmetrically related molecules into discrete pairs.
• Synthesis and evaluation of analgesic, antiinflammatory and antiplatelet properties of new 2-pyridylarylhydrazone derivatives
  作者：Adriane R. Todeschini、Ana Luisa P. de Miranda、Kelly Christine M. da Silva、Sergio C. Parrini、Eliezer J. Barreiro

  DOI：10.1016/s0223-5234(98)80008-1

  日期：1998.3

  This work describes recent results from our research program aiming at the synthesis and pharmacological evaluation of new compounds acting as antiinflammatory, analgesic and platelet antiaggregatory. In this paper the synthesis and the pharmacological profile as analgesic, antiinflammatory and anti-platelet of new functionalized 2-pyridylarylhydrazone derivatives 5a-r are discussed. This class of N-heterocyclic derivatives represents a new series of prototype candidates with analgesic and antiinflammatory properties possessing also an important anti-aggregating activity. The pharmacological results herein disclosed suggest that the antiinflammatory and analgesic activities of these new pyridynehydrazone derivatives observed in the carrageenan pleurisy model and acetic acid writhing test, respectively is probably due to an interference on the arachidonic acid (AA) metabolism. The most important antiinflammatory derivative 2-(2-formylfurane)pyridylhydrazone 5p presented a 79% inhibition of pleurisy at a dose of 80.1 mu mol/kg. We also described the results concerning the mechanism of action of this series of N-heterocyclic derivatives in platelet aggregation which suggest a Ca2+ participation, probably by a complexation scavenger mechanism. Compound 2-(2-formylfurane)pyridylhydrazone 5p was able to complex Ca2+ in in vitro experiments at 100 mu M concentration, indicating that this series of compounds can act as Ca2+ scavenger depending on the nature of the aryl moiety present at the imine subunit. (C) Elsevier, Paris.
• Hypervalent iodine mediated synthesis of 1-aryl/hetryl-1,2,4-triazolo[4,3-a] pyridines and 1-aryl/hetryl 5-methyl-1,2,4-triazolo[4,3-a]quinolines as antibacterial agents
  作者：Anil K. Sadana、Yasmin Mirza、Kamal R. Aneja、Om Prakash

  DOI：10.1016/s0223-5234(03)00061-8

  日期：2003.5

  with iodobenzene diacetate (IBD) in dichloromethane yield 1-aryl/hetryl-1,2,4-trizolo-[4,3-a] pyridines (3a-f) and 1-aryl/hetryl-5-methyl-1,2,4-triazolo[4,3-a] quinolines (6a-f). Seven compounds were tested in vitro for their antibacterial activity. 1-(5'-Nitro-2-furyl)-5-methyl-1,2,4-triazolo[4,3-a]quinoline (6e) was associated with substantially higher antibacterial activity than some commercial antibiotics

  用二氯甲烷中的碘代二苯乙酸酯（IBD）氧化2-吡啶基和2-喹啉yl，生成1-芳基/ hetryl-1,2,4-trizolo- [4,3-a]吡啶（3a-f）和1-芳基/ hetryl-5-甲基-1,2,4-三唑并[4,3-a]喹啉（6a-f）。体外测试了七种化合物的抗菌活性。1-（5'-硝基-2-呋喃基）-5-甲基-1,2,4-三唑并[4,3-a]喹啉（6e）的抗菌活性明显高于某些商业上针对鼠伤寒沙门氏菌的抗生素。 MIC，即10微克mL（-1）。