N'-(4-methylbenzoyl)-3-nitrobenzohydrazide | 311313-24-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-(4-methylbenzoyl)-3-nitrobenzohydrazide
• 英文别名: 1-[(4-methyl)benzoyl]-2-(3-nitrobenzoyl)hydrazine；N'-[(4-methylphenyl)carbonyl]-3-nitrobenzohydrazide
• CAS: 311313-24-3
• 化学式: C₁₅H₁₃N₃O₄
• 分子量: 299.286
• InChiKey: FIZNUPKXRFHQMY-UHFFFAOYSA-N

物化性质

• 沸点：
  582.4±50.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N'-(4-methylbenzoyl)-3-nitrobenzohydrazide 在 3-甲基吡啶 、 三溴化硼 、 氯化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 40.0h， 生成 2-(3,4-dihydroxyphenyl)-N-(3-(5-p-tolyl-1,3,4-oxadiazol-2-yl)phenyl)acetamide
  参考文献：
  名称：

  Design, Synthesis and Biological Activity Evaluation of 2,5-Diphenyl-1,3,4-oxadiazole Derivatives as Novel Inhibitors of Fructose-1,6-bisphosphatase

  摘要：

  Fructose-1,6-bisphosphatase (FBPase), an important gluconeogenic enzyme, catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate. The effort to discover new FBPase inhibitors was carried out by high-throughput screening (HTS) of a library of 56,000 lead-like compounds, and a 2,5-diphenyl-1,3,4-oxadiazole (3a, IC50 = 15.45 mu M) which bearing no phosphate group was identified as a potential FBPase inhibitor for the first time. Structure-activity-relationship (SAR) research of a series of analogues obtained by modifying the substituent groups and replacing the 1,3,4-oxadiazole with several other heterocycles disclosed the key structure and substituent groups related to the binding with FBPase.

  DOI：

  10.3987/com-12-12565
• 作为产物：
  描述：

  3-硝基苯甲酸甲酯 在 3-甲基吡啶 、 1-羟基苯并三唑 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 N'-(4-methylbenzoyl)-3-nitrobenzohydrazide
  参考文献：
  名称：

  Synthesis and structure–activity relationship of non-phosphorus-based fructose-1,6-bisphosphatase inhibitors: 2,5-Diphenyl-1,3,4-oxadiazoles

  摘要：

  With the aim of discovering a novel class of non-phosphorus-based fructose-1,6-bisphosphatase (FBPase) inhibitors, a series of 2,5-diphenyl-1,3,4-oxadiazoles were synthesized based on the hit compound (1) resulting from a high-throughput screening (HTS). Structure-activity relationship (SAR) studies led to the identification of several compounds with comparable inhibitory activities to AMP, the natural allosteric inhibitor of FBPase. Notably, compound 22 and 27b, bearing a terminal carboxyl or 1H-tetrazole, demonstrated remarkable inhibition to gluconeogenesis (GNG). In addition, both inhibition and binding mode to the enzyme were investigated by enzymatic kinetics and in silico experiments for representative compounds 16 and 22.

  DOI：

  10.1016/j.ejmech.2014.06.011

文献信息

• Diaryl substituted thiazoles useful in the treatment of fungal infections
  申请人：——

  公开号：US06156776A1

  公开（公告）日：2000-12-05

  Disclosed is a novel class of thiazole, thiadiazole, and oxadiazole compounds which are substituted at their nuclear carbons by aromatic moieties. These compounds exhibit antifungal activity against a variety of fungi including strains which have proven to be resistant to treatment with known antifungal agents such as Fluconazole.

  披露了一类新型的噻唑、噻二唑和噁二唑化合物，它们在核心碳上被芳香基取代。这些化合物对包括已被证明对已知抗真菌药物如氟康唑具有抗药性的各种真菌表现出抗真菌活性。
• PYRIDYL SUBSTITUTED THIAZOLES
  申请人：——

  公开号：US20010000178A1

  公开（公告）日：2001-04-05

  Disclosed is a novel class of thiazole, thiadiazole, and oxadiazole compounds which are substituted at their nuclear carbons by aromatic moieties. These compounds exhibit antifungal activity against a variety of fungi including strains which have proven to be resistant to treatment with known antifungal agents such as Fluconazole.

  本发明涉及一类新型的噻唑、噻二唑和噁二唑化合物，其核碳被芳香基取代。这些化合物对多种真菌具有抗真菌活性，包括那些已被证明对已知抗真菌药物如氟康唑治疗产生抗药性的菌株。
• Novel class of thiomorpholino substituted thiazoles
  申请人：——

  公开号：US20010000177A1

  公开（公告）日：2001-04-05

  Disclosed is a novel class of thiazole, thiadiazole, and oxadiazole compounds which are substituted at their nuclear carbons by aromatic moieties. These compounds exhibit antifungal activity against a variety of fungi including strains which have proven to be resistant to treatment with known antifungal agents such as Fluconazole.

  本发明涉及一类新型的噻唑、噻二唑和噁二唑化合物，其核碳原子被芳香族基团取代。这些化合物对多种真菌表现出抗真菌活性，包括那些已被已知抗真菌药物如氟康唑治疗后仍然耐药的菌株。
• Novel class of piperazino substituted thiazoles
  申请人：——

  公开号：US20010000512A1

  公开（公告）日：2001-04-26

  Disclosed is a novel class of thiazole, thiadiazole, and oxadiazole compounds which are substituted at their nuclear carbons by aromatic moieties. These compounds exhibit antifungal activity against a variety of fungi including strains which have proven to be resistant to treatment with known antifungal agents such as Fluconazole.

  本发明涉及一类新型的噻唑、噻二唑和噁二唑化合物，它们的核碳被芳香族基替代。这些化合物对多种真菌表现出抗真菌活性，包括那些已被证明对已知的抗真菌药物如氟康唑的治疗具有抗药性的菌株。
• Thiadiazole antifungal agents
  申请人：——

  公开号：US20020002193A1

  公开（公告）日：2002-01-03

  Disclosed is a novel class of thiazole, thiadiazole, and oxadiazole compounds which are substituted at their nuclear carbons by aromatic moieties. These compounds exhibit antifungal activity against a variety of fungi including strains which have proven to be resistant to treatment with known antifungal agents such as Fluconazole.

  本发明涉及一种新型的噻唑、噻二唑和噁二唑化合物类，其核碳被芳香基团取代。这些化合物对各种真菌表现出抗真菌活性，包括那些已被证明对已知抗真菌药物如氟康唑治疗产生抗药性的菌株。