4-anilino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitrile | 108958-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-anilino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 3-cyano-5-formyl-2-oxo-4-(phenylamino)-1,2-dihydropyridine；3-cyano-5-formyl-2-oxo-4-phenylamino-1,2-dihydropyridine；4-phenylamino-3-cyano-5-formyl-2-oxo-1,2-dihydropyridine；3-cyano-4-(N-phenylamino)-5-formyl-2-pyridone；4-anilino-3-cyano-5-formylpyridin-2-one；4-anilino-3-cyano-5-formyl-2-oxo-1,2-dihydropyridine；3-Cyano-4-anilino-5-formyl-2-pyridone；4-anilino-5-formyl-2-oxo-1H-pyridine-3-carbonitrile
• CAS: 108958-64-1
• 化学式: C₁₃H₉N₃O₂
• 分子量: 239.233
• InChiKey: JVBPGGUTMMPPPF-UHFFFAOYSA-N

物化性质

• 熔点：
  280 °C (decomp)
• 沸点：
  359.7±42.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 溶解度：
  >35.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-anilino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 3.0h， 以70%的产率得到3-cyano-5-hydroxymethyl-2-oxo-4-phenylamino-1,2-dihydropyridine
  参考文献：
  名称：

  Synthesis and functionalization of 4-arylamino-2-pyridone derivatives

  摘要：

  根据烯酰胺与二甲基甲酰胺二甲基缩醛的反应，开发了合成以前未知的嘧啶、4-氨基-2-吡啶酮和 4-氨基吡啶衍生物的新方法。对 4-氨基-2-吡啶酮衍生物进行了新的结构改造。制备出了许多对生物研究有意义的此类化合物。

  DOI：

  10.1007/s11172-006-0443-4
• 作为产物：
  描述：

  2-氰基-3-二甲基氨基-2-丁酰胺 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 41.0h， 生成 4-anilino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  [EN] CPAP-TUBULIN MODULE
  [FR] MODULE DE TUBULINE CPAP

  摘要：

  这项发明涉及具有一般式（1）或其生理上可接受的盐的CPAP-微管蛋白抑制剂；以及它们作为抗癌治疗药物的用途。

  公开号：

  WO2017097928A1

文献信息

• Substituted 3-and 5-formylpyridin-2-ones in the synthesis of 1-aryl-1, 6-naphthyridinone derivatives
  作者：M. I. Medvedeva、N. Z. Tugusheva、L. M. Alekseeva、M. I. Evstratova、S. S. Kiselev、V. V. Chernyshev、G. V. Avramenko、V. G. Granik

  DOI：10.1007/s11172-009-0325-7

  日期：2009.11

  the action of various CH acids. A new approach to the synthesis of 4-(4-fluoroanilino)-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitrile using dimethylformamide diisopropylacetal under mild conditions was developed. The comparative reactivity of the formyl group in the reactions of 4-arylamino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitriles and in 4-arylamino-2-oxo-1,2-dihydropyridine-3-carb-aldehydes

  新的 1-aryl-6-[2-(二甲基氨基)vinyl]4-oxo-1,4-dihydropyrimidine-5-carbonitriles 和 4-arylamino-2-oxo-1,2-dihydropyridine-3-carbonitriles 含吸电子苯环中的取代基由烯氨基酰胺和二甲基甲酰胺二烷基缩醛合成。研究了反应中各种二甲基甲酰胺缩醛对3-(4-氯-苯胺基)-2-氰基-5-(二甲氨基)五-2,4-二烯酸N-(二甲氨基)亚甲基酰胺产率的影响这些缩醛与 3-(4-氯苯胺)-2-氰基巴豆酰胺。新的 4-arylamino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitriles 和 4-arylamino-2-oxo-1,2-dihydropyridine-3-carbaldehydes 在苯环中含有吸电子取代基合成的。后一种化合物被转化为新的取代
• New approach to the synthesis of 4-amino-2-pyridone and 1-phenyl-1,6-naphthyridinone derivatives based on substituted 3-and 5-formyl-2-pyridones
  作者：N. Z. Tugusheva、L. M. Alekseeva、A. S. Shashkov、V. G. Granik

  DOI：10.1007/s11172-006-0442-5

  日期：2006.8

  The reactions of 3-cyano-3(5)-formyl-2-oxo-4-(phenylamino)-1,2-dihydropyridines with CH acids were studied. The previously unknown fused 2-pyridone derivatives containing the 4-aminopyridine fragment were synthesized by the Knoevenagel reaction.

  研究了 3-氰基-3(5)-甲酰基-2-氧代-4-(苯基氨基)-1,2-二氢吡啶与 CH 酸的反应。通过 Knoevenagel 反应合成了以前未知的含有 4- 氨基吡啶片段的融合 2-吡啶酮衍生物。
• Reactions of aminoguanidine and guanidine with 3- and 5-formyl-4-arylaminopyridones
  作者：M. I. Medvedeva、N. Z. Tugusheva、L. M. Alekseeva、M. A. Kalinkina、V. A. Parshin、V. V. Chernyshev、V. I. Levina、N. B. Grigor’ev、A. S. Shashkov、V. G. Granik

  DOI：10.1007/s11172-010-0385-8

  日期：2010.12

  investigate their biological activity as putative NO donors. The reaction of 5- и 3-formylpyridones with diguanidinium carbonate was studied. The formation of stable complexes of 4-arylamino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitriles with aminoguanidine and guanidine was discovered. Amidinohydrazones obtained possess antiinflammatory, antidiabetic, and antihypertensive activities.

  脒腙是通过 4-arylamino-2-oxo-5-formyl-1,2-dihydropyridine-3-carbonitriles 和 4-arylamino-2-oxo-1,2-dihydropyridine-3-carbaldehydes 与氨基胍碳酸盐与目的是研究它们作为推定的 NO 供体的生物活性。研究了 5- 和 3-甲酰基吡啶酮与碳酸二胍的反应。发现了 4-芳基氨基-5-甲酰基-2-氧代-1,2-二氢吡啶-3-甲腈与氨基胍和胍的稳定复合物的形成。获得的脒腙具有抗炎、抗糖尿病和抗高血压活性。
• Synthesis and hydrolytic cleavage of 1-aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo(thioxo)-1,4-dihydropyrimidines
  作者：A. S. Ivanov、N. Z. Tugusheva、L. M. Alekseeva、V. G. Granik

  DOI：10.1023/b:rucb.0000037857.07190.75

  日期：2004.4

  1-Aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo-1,4-dihydropyrimidines and their 4-thioxo analogs, which were prepared in three steps from cyanoacetamide and cyanothioacetamide, respectively, were subjected to hydrolysis. In aqueous AcOH, hydrolysis of N-(dimethylaminomethylene)-2-cyano-5-dimethylamino-2,4-pentadieneamide derivatives containing amino groups at position 3 afforded formylpyridones. The reaction of 2-cyano-3-dimethylaminothiocrotonamide with DMF dimethyl acetal gave rise to 3-cyano-4-dimethylamino-2-methylthiopyridine.
• ——
  作者：A. S. Ivanov、N. Z. Tugusheva、N. P. Solov"eva、V. G. Granik

  DOI：10.1023/a:1021636632164

  日期：——

  The reactions of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (4) with S-, C-, and N-nucleophiles afford stable sigma-adducts at position 10. In the base-catalyzed reactions of compound 4 with thiols, the resulting sigma-complexes are rearranged into sulfides 14a-c. Sulfides 14b,c undergo the Thorpe-Ziegler cyclization to give 1-aminobenzo[b]thieno[2,3-h][1,6]naphthyridine derivatives 15a,b. The reaction of naphthyridine 4 with aniline affords a mixture of sigma-adducts of the C-N and C-C types, while those with aliphatic amines yield 3-amino derivatives 17a-c. In the presence of H2O2, benzonaphthyridine 4 adds peroxycarboxylic acids to give compounds 8a,b. In alkaline medium, adduct 8a is rearranged into 4-aminopyridine-3-carbaldehyde derivative 10.