2-oxo-N-m-tolyl-2H-chromene-3-carboxamide | 1846-99-7

• 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: 2-oxo-N-m-tolyl-2H-chromene-3-carboxamide
• 英文别名: N-(3′-methylphenyl)coumarin-3-carboxamide；N-(3-methylphenyl)-2-oxo-2H-chromene-3-carboxamide；Coumarin-3-carbonsaeure-N-<3-methyl-phenylamid>；2-oxo-2H-chromene-3-carboxylic acid m-toluidide；2-Oxo-2H-chromen-3-carbonsaeure-m-toluidid；N-(3-methylphenyl)-2-oxochromene-3-carboxamide
• CAS: 1846-99-7
• 化学式: C₁₇H₁₃NO₃
• mdl: MFCD00249917
• 分子量: 279.295
• InChiKey: XUNAVIWFCXQWCJ-UHFFFAOYSA-N

物化性质

• 熔点：
  202 °C
• 沸点：
  541.4±50.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)
• 溶解度：
  <0.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-N-m-tolyl-2H-chromene-3-carboxamide 在 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.5h， 生成 N-furfurylsalicylaldimine
  参考文献：
  名称：

  Islam, A. M.; Bedair, A. H.; Aly, F. M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 3, p. 224 - 226

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-Dihydrocumarin-3-carbonsaeure 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 2-oxo-N-m-tolyl-2H-chromene-3-carboxamide
  参考文献：
  名称：

  New 2H-chromene-3-carboxamide derivatives: Design, synthesis and use as inhibitors of hMAO

  摘要：

  A series new 2H-chromene-3-carboxamide derivatives 4a-4t were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. Among them, compound 4d (IC50 = 0.93 μM, IC(50 iproniazid) = 7.80 μM) showed the most activity and higher MAO-B selectivity (64.5-fold vs. 1-fold) with respect to the MAO-A isoform. The active compound 4d was also docked into the hMAO-B complex structure active site to determine the probable binding model. The results indicated that conserved residue CYSA 172 was important for ligand binding via hydrogen bond interaction, Pi-Pi interaction was found between the benzene-ring of compound 4d and residue ILEA 199.

  DOI：

  10.1016/j.ejmech.2014.04.060

文献信息

• Coumarins and adenosine receptors: New perceptions in structure-affinity relationships
  作者：André Fonseca、Maria João Matos、Santiago Vilar、Sonja Kachler、Karl-Norbert Klotz、Eugenio Uriarte、Fernanda Borges

  DOI：10.1111/cbdd.13075

  日期：2018.1

  Adenosine receptor (AR) subtypes are involved in several physiological and pharmacological processes. Ligands that are able to selectively modulate one receptor subtype can delay or slow down the progression of diverse diseases. In this context, our research group focused its investigation into the discovery and development of novel, potent and selective AR ligands based on coumarin scaffold. Therefore

  腺苷受体（AR）亚型涉及几种生理和药理过程。能够选择性调节一种受体亚型的配体可以延缓或减缓多种疾病的发展。在这种情况下，我们的研究小组将研究重点放在了基于香豆素骨架的新型，有效和选择性AR配体的发现和开发上。因此，一系列的3-phenylcarboxamidocoumarins合成以及它们在人AR亚型的亲和性是通过放射性配体结合测定法用于筛选阿1，A 2A和A 3个受体和对于A 2B由腺苷酸环化酶测定。发现化合物26最显着，其h A1 / ħ甲3和ħ甲2A / ħ甲3选择性的42，为A 3 AR（ķ我 = 2.4μ米）。受体驱动的分子建模研究为化合物26的结合/选择性数据以及随后的优化过程提供了有价值的信息。此外，化合物26根据与该概念有关的一般指导原则表现出药物样性质。
• 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。
• ABCA-1 elevating compounds
  申请人：——

  公开号：US20030220356A1

  公开（公告）日：2003-11-27

  The present invention provides compounds that elevate cellular expression of the ABCA-1 gene, promoting cholesterol efflux from cells and increasing HDL levels in the plasma of a mammal, in particular humans. The compounds are useful for treating coronary artery disease.

  本发明提供了一种能够提高ABCA-1基因细胞表达的化合物，促进胆固醇从细胞中流出并增加哺乳动物（尤其是人类）血浆中的高密度脂蛋白水平。这些化合物可用于治疗冠心病。
• Synthesis, Molecular Modeling, and Selective Inhibitory Activity against Human Monoamine Oxidases of 3-Carboxamido-7-Substituted Coumarins
  作者：Franco Chimenti、Daniela Secci、Adriana Bolasco、Paola Chimenti、Bruna Bizzarri、Arianna Granese、Simone Carradori、Matilde Yáñez、Francisco Orallo、Francesco Ortuso、Stefano Alcaro

  DOI：10.1021/jm801496u

  日期：2009.4.9

  A large series of 3-carboxamido-7-substituted cournarins have been synthesized and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Taking into account all the relevant structural information on MAOs reported in the literature, we made some changes in the coumarin nucleus and examined with particular attention the effect on activity and selectivity of substituting at position 3 with N-aryl or N-alkyl carboxamide and at position 7 with a benzyloxy or a 4'-F-benzyloxy group. Some of the assayed compounds proved to be potent, selective inhibitors of hMAO-B with IC50 values in the micromolar range. To better understand the enzyme-inhibitor interaction and to explain the selectivity of the most active compounds toward hMAOs, molecular modeling studies were carried out on new, high resolution, hMAO-A and hMAO-B crystallographic structures.
• CCLXXX.—The condensation of aromatic aldehydes with malonanilic acid and its derivatives
  作者：Gurcharan Singh Ahluwalia、Muhammad Abdul Haq、Jñanendra Nath Rây

  DOI：10.1039/jr9310002059

  日期：——