2-oxo-2H-1-benzopyran-3-carboxylic acid 2-(2-oxo-2H-1-benzopyran-3-carbonyl)hydrazide | 99275-34-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-oxo-2H-1-benzopyran-3-carboxylic acid 2-(2-oxo-2H-1-benzopyran-3-carbonyl)hydrazide
• 英文别名: N,N-bis-(coumarin-3-yl)hydrazide；2-oxo-N'-(2-oxo-2H-chromene-3-carbonyl)-2H-chromene-3-carbohydrazide；2-oxo-N'-(2-oxochromene-3-carbonyl)chromene-3-carbohydrazide
• CAS: 99275-34-0
• 化学式: C₂₀H₁₂N₂O₆
• 分子量: 376.325
• InChiKey: ZELRTNFSPDNXCR-UHFFFAOYSA-N

物化性质

• 熔点：
  >360 °C
• 沸点：
  768.8±60.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-oxo-2H-1-benzopyran-3-carboxylic acid 2-(2-oxo-2H-1-benzopyran-3-carbonyl)hydrazide 在 sodium hydroxide 作用下， 生成 香豆素-3-羧酸
  参考文献：
  名称：

  Bonsignore, Leonardo; Cabiddu, Salvatore; Loy, Giuseppe, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 463 - 464

  摘要：

  DOI：
• 作为产物：
  描述：

  2-cyano-N'-(2-cyanoacetyl)acetohydrazide 在 盐酸 、 sodium hydroxide 作用下， 反应 3.0h， 生成 2-oxo-2H-1-benzopyran-3-carboxylic acid 2-(2-oxo-2H-1-benzopyran-3-carbonyl)hydrazide
  参考文献：
  名称：

  Design, green one-pot synthesis and molecular docking study of novel N,N-bis(cyanoacetyl)hydrazines and bis-coumarins as effective inhibitors of DNA gyrase and topoisomerase IV

  摘要：

  A novel, quick, environmentally safe, and one-pot synthesis of a series of N,N-bis(cyanoacetyl)hydrazine derivatives, bis-imino-2H-chromenes and bis-2-oxo-2H-chromene derivatives have been designed. Some selected newly synthesized compounds were investigated in vitro for their antibacterial activity. Compound 5j is the most toxic compound against Staphylococcus aureus with activity index 171%, followed by compound 15b with activity index 136% compared to standard drug ampicillin. Moreover, compound 15a is the most toxic compound against Escherichia coli with activity index 111% compared to standard drug gentamicin. Minimum inhibitory concentration (MIC) was carried out for compounds with high antibacterial activity. Compound 5j has good MIC (7.8 mu g/ml) against Staphylococcus aureus while 15a has good MIC (31.25 mu g/ml) against Streptococcus mutans which is better than MIC of the standard drug ampicillin (MIC = 62.5 mu g/ml). Compounds 5j, 5k, 15a, 15b and 15e which have good MIC values were introduced to enzyme assay against DNA gyrase and topoisomerase IV. The results showed that compound 15a can strongly inhibit DNA gyrase and topoisomerase IV (IC50 = 27.30 and 25.52 mu M respectively), compared to methotrexate as the standard drug (IC50 = 29.01 and 23.55 mu M respectively). Structure-activity relationships were also discussed based on the biological and docking simulation results.

  DOI：

  10.1016/j.bioorg.2020.103672

文献信息

• Synthesis of novel coumarin and benzocoumarin derivatives and their biological and photophysical studies
  作者：Alaa S. Abd-El-Aziz、Hany M. Mohamed、Shawkat Mohammed、Shamsulhaq Zahid、Athar Ata、Ahmed H. Bedair、Ahmed M. El-Agrody、Pierre D. Harvey

  DOI：10.1002/jhet.5570440610

  日期：2007.11

  The reaction of 1-chloromethylbenzo[f]coumarins (36) with cyanide anion under different reaction conditions was also investigated in order to assess its suitability for nucleophilic substitution reactions as well as ring transformation products (43-49). Synthesis of 1-((benzo[d]thiazol-2-yl)methyl)-9-hydroxybenzo[f]coumarin (50) represented the first example of methylene bridge-head heterocyclecontaining

  通过香豆素-3-羰基氯（1）与许多亲核试剂的反应已经制备了香豆素-3 N-羧酰胺的几种衍生物（3-21）。还使用相同的方法制备了新型双头香豆素-3 N-羧酰胺（26-33）。应用Pechmann-Duisberg反应制备新的苯并[ f ]-苯并[ h ]香豆素和4-（氯甲基）-吡喃并[3,2 - c ]香豆素-2-酮（36-42）。1-氯甲基苯并[ f ]香豆素的反应（36）还研究了在不同反应条件下与氰化物阴离子形成的阴离子，以评估其对亲核取代反应以及环转化产物的适用性（43-49）。1-（（苯并[ d ]噻唑-2-基）甲基）-9-羟基苯并[ f ]香豆素（50）的合成代表了含亚甲基桥头杂环的苯并[ f ]香豆素的第一个实例。一些新制备的香豆素对革兰氏阳性和革兰氏阴性细菌表现出抗菌活性。发现化合物36d对所有经筛选的细菌具有活性。对选定的荧光苯并[ f ]-和苯并[ h ]进行了光物理研究
• BONSIGNORE, L.;CABIDDU, S.;LOY, G.;SECCI, M., J. HETEROCYCL. CHEM., 1985, 22, N 2, 463-464
  作者：BONSIGNORE, L.、CABIDDU, S.、LOY, G.、SECCI, M.

  DOI：——

  日期：——