imidazole-1-carbonyl-chromenone | 886124-83-0

• 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: imidazole-1-carbonyl-chromenone
• 英文别名: 3-(Imidazole-1-carbonyl)chromen-2-one
• CAS: 886124-83-0
• 化学式: C₁₃H₈N₂O₃
• 分子量: 240.218
• InChiKey: PJIBPAWORAWNJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  imidazole-1-carbonyl-chromenone 在 一水合肼 作用下， 反应 0.02h， 生成 2-氧酰肼-2H-1-苯并吡喃-3-羧酸
  参考文献：
  名称：

  Khan, Khalid Mohammed; Salar, Uzma; Fakhri, Muhammad Imran, Letters in Organic Chemistry, 2015, vol. 12, # 9, p. 637 - 644

  摘要：

  DOI：
• 作为产物：
  描述：

  香豆素-3-羧酸 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 imidazole-1-carbonyl-chromenone
  参考文献：
  名称：

  异构3-异恶二唑基香豆素及其衍生物

  摘要：

  在这里，我们代表了异构体3-异二唑基香豆素及其衍生物的合成制备方法。对于3- [1,2,4-恶二唑-5-基]香豆素I，已经开发出两种新的合成方法。第一种方法基于香豆素-; 3-羧酸，1,1'-羰基二咪唑和a胺肟的三组分缩合。第二种方法本质上是利用5-氰基甲基1,2,4-恶二唑与水杨醛的相互作用。已经制定了制备3- [1,2,4-恶二唑-3-基]香豆素II的一般方法。此外，上述合成方法为2-亚同价衍生物III和IV的合成开辟了道路。 之前没有描述，通过亚氨基2-亚氨基与许多氨基化合物的亲核取代反应使这些化合物多样化。

  DOI：

  10.1002/jhet.893

文献信息

• 1,1'-Carbonyldiimidazole (CDI) Mediated Facile Synthesis, Structural Characterization, Antimicrobial Activity, and in-silico Studies of Coumarin- 3-carboxamide Derivatives
  作者：Uzma Salar、Khalid M. Khan、Muhammad I. Fakhri、Shafqat Hussain、Saima Tauseef、Shagufta Ameer、Abdul Wadood、Huma Khan、Shahnaz Perveen

  DOI：10.2174/1573406413666170623083116

  日期：2018.1.11

  Background: Despite the availability of a variety of antibacterial agents, re-emergence of pathogenic bacteria is still a serious medical concern. So, identification of new, safer, and selective antibacterial agents is the key interest in the medicinal chemistry research. Method: To explore the antimicrobial activity of coumarin-3-carboxamides for a range of bacterial and fungal strains, twenty eight derivatives were synthesized by the reaction of coumarin-3-carboxylic acid with a variety of aniline derivatives in the presence of 1,1'-carbonyldiimidazole (CDI). All compounds were structurally characterized by different spectroscopic techniques EI-MS, HREI-MS, 1H-NMR, 13C-NMR, and evaluated for antimicrobial activities (antibacterial and antifungal). Results: A number of compounds showed good to weak antibacterial activity against various strains of Gram-positive and Gram-negative bacteria. Amongst them, compound 28 displayed noticeable inhibition against five strains of Gram-positive (Bacillus subtilis, Corynebacterium xerosis, Staphylococcus aureus, Streptococcus faecalis, and MRSA) and four strains of Gram-negative bacteria (Klebsiella pneumoniae, Pseudomonas aeruginosa, Enterobacter aerogene, and Shigella dysenteria). However, none of the compounds showed antifungal activity against tested fungi. MIC values were determined for most of the active compounds 2, 15, and 28 against particular bacterial cultures. In silico studies were performed on the most active compound 28 in order to specify and verify the target for antibacterial activity of synthetic coumarin-3-carboxamide derivatives. The cytotoxicity of these compounds on mammalian cells is unknown yet but we are planning to carry out research on the cytotoxic aspect of these compounds in future. Conclusion: The newly identified compounds may serve as lead molecules for the future research regarding the identification of new antibacterial agents.

  背景：尽管已有多种抗菌剂可用，但致病菌的重新出现仍然是一个严重的医学问题。因此，鉴定新型更安全和选择性的抗菌剂是药物化学研究的关键兴趣。 方法：为了探索香豆素-3-羧酰胺对多种细菌和真菌菌株的抗微生物活性，通过将香豆素-3-羧酸与多种苯胺衍生物在1,1'-羰基二咪唑（CDI）存在下反应合成了28种衍生物。所有化合物均采用不同的光谱技术（EI-MS、HREI-MS、1H-NMR、13C-NMR）进行结构表征，并评估其抗微生物活性（抗菌和抗真菌）。 结果：多种化合物对不同的革兰阳性和革兰阴性菌株显示良好到弱的抗菌活性。其中，化合物28对五种革兰阳性菌（枯草芽孢杆菌、干燥棒状杆菌、金黄色葡萄球菌、屎肠球菌和耐甲氧西林金黄色葡萄球菌）和四种革兰阴性细菌（肺炎克雷伯菌、铜绿假单胞菌、嗜麦芽窄食杆菌和志贺菌）表现出显著的抑制作用。然而，所有化合物在测试的真菌中均未显示抗真菌活性。对大多数活性化合物2、15和28在特定细菌培养物上的最低抑菌浓度（MIC）进行了测定。针对最活跃的化合物28进行了分子模拟研究，以明确和验证合成香豆素-3-羧酰胺衍生物的抗菌活性靶点。这些化合物对哺乳动物细胞的细胞毒性尚未确定，但我们计划在未来对这些化合物的细胞毒性方面进行研究。 结论：新鉴定的化合物可作为未来研究新抗菌剂的先导分子。
• Isomeric 3-Isoxadiazolylcoumarins and Their Derivatives
  作者：Oleksandr S. Detistov、Valeriy D. Orlov、Irina O. Zhuravel'

  DOI：10.1002/jhet.893

  日期：2012.7

  Here, we represent preparative methods of synthesis of isomeric 3‐isoxadiazolylcoumarins and their derivatives. Two new synthetic methods have been developed for 3‐[1,2,4‐oxadiazol‐5‐yl]coumarins I. The first method is based on a three‐component condensation of coumarin‐;3‐carboxylic acids, 1,1′‐carbonyldiimidazole, and amidoximes. The second method essentially uses the interaction of 5‐cyanomethyl‐1

  在这里，我们代表了异构体3-异二唑基香豆素及其衍生物的合成制备方法。对于3- [1,2,4-恶二唑-5-基]香豆素I，已经开发出两种新的合成方法。第一种方法基于香豆素-; 3-羧酸，1,1'-羰基二咪唑和a胺肟的三组分缩合。第二种方法本质上是利用5-氰基甲基1,2,4-恶二唑与水杨醛的相互作用。已经制定了制备3- [1,2,4-恶二唑-3-基]香豆素II的一般方法。此外，上述合成方法为2-亚同价衍生物III和IV的合成开辟了道路。 之前没有描述，通过亚氨基2-亚氨基与许多氨基化合物的亲核取代反应使这些化合物多样化。
• Practical and Selective Syntheses of <i>S</i>‐Acyl and <i>N</i>‐Acyl Glutathiones with <i>N</i>‐Acyl Imidazoles in Water
  作者：Michele Retini、Andrea Sisti、Diego Olivieri、Michele Mari、Francesca Bartoccini、Giovanni Piersanti

  DOI：10.1002/ejoc.202400255

  日期：——

  We report a simple and efficient glutathione acylation reaction for the chemoselective synthesis of S- or N-acylated glutathione derivatives, under mild conditions and using water as the solvent, by means of the in-situ formation of acyl imidazole electrophiles from the respective abundant carboxylic acid.

  我们报道了一种简单而有效的谷胱甘肽酰化反应，用于化学选择性合成 S- 或 N-酰化谷胱甘肽衍生物，在温和条件下并使用水作为溶剂，通过从各自丰富的羧基原位形成酰基咪唑亲电子试剂酸。
• Khan, Khalid Mohammed; Salar, Uzma; Fakhri, Muhammad Imran, Letters in Organic Chemistry, 2015, vol. 12, # 9, p. 637 - 644
  作者：Khan, Khalid Mohammed、Salar, Uzma、Fakhri, Muhammad Imran、Taha, Muhammad、Hameed, Abdul、Perveen, Shahnaz、Voelter, Wolfgang

  DOI：——

  日期：——
• Synthesis of Novel Coumarin Derivatives and in vitro Biological Evaluation as Potential PTP 1B Inhibitors
  作者：Honggang Zhou、Wei Liu、Cheng Sun、Chune Peng、Jian Wang、Quan Wang、Cheng Yang

  DOI：10.3987/com-13-12730

  日期：——

  The aim of protein tyrosine phosphatase 1B (PTP 1B) inhibitors is to develop effective drug for diabetes and obesity. Coumarin becomes as a good skeleton, and is often applied in drug design and synthesis. In this paper, we have synthesized a series of novel coumarin derivatives to be as potential PTP 1B inhibitors. The inhibition rate of compound 9 was more than 80%, and the IC50 value was 49.2 mu M, which would be considered for further study.