N-(4-iodophenyl)-2-oxo-2H-chromene-3-carboxamide | 92792-09-1

• 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-iodophenyl)-2-oxo-2H-chromene-3-carboxamide
• 英文别名: N-(4-iodophenyl)-2-oxochromene-3-carboxamide
• CAS: 92792-09-1
• 化学式: C₁₆H₁₀INO₃
• mdl: MFCD00728108
• 分子量: 391.165
• InChiKey: NRQJGVGVCDKKAK-UHFFFAOYSA-N

物化性质

• 熔点：
  236 °C
• 沸点：
  586.0±50.0 °C(Predicted)
• 密度：
  1.813±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  香豆素-3-羧酸 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 16.5h， 生成 N-(4-iodophenyl)-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  1,1'-Carbonyldiimidazole (CDI) Mediated Facile Synthesis, Structural Characterization, Antimicrobial Activity, and in-silico Studies of Coumarin- 3-carboxamide Derivatives

  摘要：

  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。

  DOI：

  10.2174/1573406413666170623083116

文献信息

• Novel coumarin-3-(N-aryl)carboxamides arrest breast cancer cell growth by inhibiting ErbB-2 and ERK1
  作者：Natala Srinivasa Reddy、Kiranmai Gumireddy、Muralidhar R. Mallireddigari、Stephen C. Cosenza、Padmavathi Venkatapuram、Stanley C. Bell、E. Premkumar Reddy、M.V. Ramana Reddy

  DOI：10.1016/j.bmc.2005.02.051

  日期：2005.5

  A series of novel coumarin carboxamides were synthesized, and their tumor cell cytotoxic activity was investigated. These compounds specifically inhibited the growth of cancer cells that have a high level of ErbB-2 expression. Immunoprecipitation analysis of the cell lysates prepared from carboxamide treated cancer cells showed the inhibition of ErbB-2 phosphorylation suggesting the interaction of these compounds with ErbB-2 receptor. The down regulation of the kinase activity was further confirmed by performing in vitro kinase assay with recombinant ErbB-2 incubated with carboxamides. The inhibition of ErbB-2 phosphorylation correlated with down-regulation of ERK1 MAP kinase activation that is involved in proliferative signaling pathway. Furthermore, the cell-killing activity of many of these inhibitors is restricted to tumor cells with no demonstrable cytotoxicity against normal human fibroblasts suggesting that these compounds are tumor-specific. (c) 2005 Elsevier Ltd. All rights reserved.
• 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。