2-phenyl-1,8-naphthyridine-3-carboxylic acid hydrazide | 129803-99-2

• 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: 2-phenyl-1,8-naphthyridine-3-carboxylic acid hydrazide
• 英文别名: 1,8-Naphthyridine-3-carboxylic acid, 2-phenyl-, hydrazide；2-phenyl-1,8-naphthyridine-3-carbohydrazide
• CAS: 129803-99-2
• 化学式: C₁₅H₁₂N₄O
• 分子量: 264.286
• InChiKey: PVCSZPOBQDFNNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-1,8-naphthyridine-3-carboxylic acid hydrazide 在 碘苯二乙酸 作用下， 反应 2.0h， 以94%的产率得到2-phenyl-N'-(2-phenyl-1,8-naphthyridine-3-carbonyl)-1,8-naphthyridine-3-carbohydrazide
  参考文献：
  名称：

  Mogilaiah; Babu Rao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 3, p. 235 - 236

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-phenyl-1,8-naphthyridine-3-carboxylate 在 一水合肼 作用下， 以70%的产率得到2-phenyl-1,8-naphthyridine-3-carboxylic acid hydrazide
  参考文献：
  名称：

  Synthesis, Antimicrobial Activities and Molecular Docking Studies of New N-Acylated Derivatives of 5-(2-Phenyl-1,8-naphthyridin-3-yl)-1,3,4-oxadiazol-2-amine

  摘要：

  Present study establishes a novel synthetic route of N-acetylated derivatives of 5-(2-phenyl-1,8-naphthyridine-3-yl)-1,3,4-oxadiazole-2-amine (6a-j), which was achieved in four steps with good yields. 2-Amino nicotinaldehyde and ethyl 3-oxo-3-phenylpropanoate on refluxing with triethylamine in ethanol undergoes Friedlander synthesis to furnish ethyl 2-phenyl-1,8-naphthyridine-3-carboxylate, which further converted into 2-phenyl-1,8-naphthyridine-3-carbohydrazide by reacting with hydrazine hydrate upon reflux, followed by cyclization with cyanogen bromide in the presence of water and 1,4-dioxane with sodium bicarbonate to afford 5-(2-phenyl-1,8-naphthyridin-3-yl)-1,3,4-oxadiazol-2-amine (5). Compound 5 was acetylated using numerous symmetrical anhydrides to synthesize novel N-acetylated derivatives (6a-j). The IR, 1H, 13C NMR and mass spectral analysis were used to characterize the structure of synthetic compounds. The synthesized compounds were evaluated for their antimicrobial efficiency against bacteria (S. aureus and E. coli) using ampicillin as a standard reference and against fungi (C. albicans) using fluconazole as a standard reference. Compound 6e exhibited good antibacterial properties while compounds 6c and 6e had shown high antifungal activity, whereas remaining compounds shown moderate to weaker antimicrobial activity. The synthesized derivatives verified their docking strength against Mtb MurB (PDB ID: 5JZX) and showed significant docking activity, however, compound 6f (-10.98 kcal/mol) and compound 6b (-10.52 kcal/mol) had a strong binding affinity compared to the other synthesized compounds.

  DOI：

  10.14233/ajchem.2024.30953

文献信息

• Mild and Efficient Synthesis of Phthalazine-1,4-diones Using PTSA in the Solid State
  作者：K. Mogilaiah、D. Srinivasa Chowdary、P.Raghotham Reddy、N.Vasudeva Reddy

  DOI：10.1081/scc-120015568

  日期：2003.3

  Abstract A rapid and efficient method for the synthesis of 1,8-naphthyridine-3-carbonyl phthalazine-1,4-diones by the condensation of 1,8-naphthyridine-3-carboxylic acid hydrazides with phthalic anhydride using p-toluenesulphonic acid (PTSA) as a catalyst under solid state conditions has been described. The reaction proceeds efficiently at room temperature in excellent yields and in a state of high purity

  摘要 采用对甲苯磺酸将 1,8-萘啶-3-羧酸酰肼与邻苯二甲酸酐缩合，快速高效地合成 1,8-萘啶-3-羰基酞嗪-1,4-二酮（ PTSA) 作为固态条件下的催化剂已有描述。该反应在室温下以极好的收率和高纯度有效进行。
• Microwave assisted synthesis of thiazolo[3,2-<i>b</i>][1,2,4]-triazoles containing 1,8-naphthyridine moiety
  作者：K. Mogilaiah、M. Prashanthi、S. Kavitha、H. Sharath Babu

  DOI：10.1002/jhet.5570440530

  日期：2007.9

  A simple and efficient protocol for the synthesis of 5-aryl-2-(2-substituted-1,8-naphthyridin-3-yl)-thiazolo[3,2-b][1,2,4]triazoles (4) is achieved by cyclocondensation of 3-(2-substituted-1,8-naphthyridin-3-yl)-1,2,4-triazoles (3) with α-halogenoketones in anhyd. methanol under microwave irradiation. The products are obtained in good yields and in a state of high purity.

  一种简单而有效的合成5-芳基-2-（2-取代的1,8-萘啶-3-基）-噻唑并[3,2- b ] [1,2,4]三唑的方案（4）通过将3-（2-取代的1,8-萘啶-3-基）-1,2,4-三唑（3）与α-卤代酮在酸酐中进行环缩合可实现。微波辐射下的甲醇。以高收率和高纯度获得产物。
• Mogilaiah; Kankaiah, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 3, p. 658 - 660
  作者：Mogilaiah、Kankaiah

  DOI：——

  日期：——
• Mogilaiah; Srinivasa Chowdary; Babu Rao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 1, p. 43 - 48
  作者：Mogilaiah、Srinivasa Chowdary、Babu Rao

  DOI：——

  日期：——
• Rama Rao; Mogilaiah; Sreenivasulu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 4, p. 339 - 344
  作者：Rama Rao、Mogilaiah、Sreenivasulu

  DOI：——

  日期：——