2-oxo-N-(3-(trifluoromethyl)phenyl)-2H-chromene-3-carboxamide | 301196-52-1

• 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: 2-oxo-N-(3-(trifluoromethyl)phenyl)-2H-chromene-3-carboxamide
• 英文别名: 2-oxo-N-[3-(trifluoromethyl)phenyl]-2H-chromene-3-carboxamide；2-oxo-N-[3-(trifluoromethyl)phenyl]chromene-3-carboxamide
• CAS: 301196-52-1
• 化学式: C₁₇H₁₀F₃NO₃
• mdl: MFCD00584200
• 分子量: 333.267
• InChiKey: JXUJVKNPEQUAAV-UHFFFAOYSA-N

物化性质

• 熔点：
  210-211 °C
• 沸点：
  521.3±50.0 °C(Predicted)
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 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：
  6

反应信息

• 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-(3-(trifluoromethyl)phenyl)-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

• Design, Synthesis and In Vitro Evaluation of 2-Oxo-N-substituted Phenyl- 2H-chromene-3-carboxamide Derivatives as HIV Integrase Strand Transfer Inhibitors
  作者：Pankaj Wadhwa、Priti Jain、Hemant R. Jadhav

  DOI：10.2174/1570180816666190617150803

  日期：2020.4.25

  been evaluated for HIV-1 integrase (IN) inhibition. Methods: The derivatives were synthesized via a two-step pathway commencing with 2- hydroxybenzaldehyde and diethyl malonate followed by hydrolysis of ester and coupling with various aromatic amines. The HIV-1 IN inhibitory potential of these compounds has been studied relative to dolutegravir, a known HIV-1 IN inhibitor using a standard available

  背景：已经评估了一系列18个2-氧-N-取代的苯基-2H-色烯-3-羧酰胺类似物对HIV-1整合酶（IN）的抑制作用。 方法：衍生物是通过两步途径从2-羟基苯甲醛和丙二酸二乙酯开始合成，然后将酯水解并与各种芳香胺偶联。已使用标准可用试剂盒相对于已知的HIV-1 IN抑制剂dolutegravir研究了这些化合物的HIV-1 IN抑制潜力。 结果：六个分子（化合物13h，13i，13l，13p至13r）显示出对HIV-1整合酶3'链转移的显着抑制作用，IC50值小于1.7μM。苯甲基-3-羧酰胺基序的存在对酶活性至关重要。此外，还进行了分子建模研究以证明IN抑制的合理性，并得出了体外-计算机相关性。 结论：然而，这些化合物在其细胞毒性浓度以下均未显示HIV-1和HIV-2抑制作用，表明这些化合物无法进一步用于抗HIV活性，因此需要进行结构修饰。
• Methods of Inhibiting Bacterial Virulence and Compounds Relating Thereto
  申请人：Sperandio Vanessa

  公开号：US20100048573A1

  公开（公告）日：2010-02-25

  The present invention relates to compounds and methods for the treatment of bacterial infections. Because their mechanism of action does not involve killing of bacteria or inhibiting their growth, the potential for these compounds to induce drug resistance in bacteria is minimized. Through inhibiting bacterial virulence, the present invention provides a novel means of treating bacterial infections.

  本发明涉及化合物和方法，用于治疗细菌感染。由于它们的作用机制不涉及杀死细菌或抑制它们的生长，这些化合物诱导细菌耐药性的潜力被最小化。通过抑制细菌的毒力，本发明提供了治疗细菌感染的新方法。
• 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.
• US8252841B2
  申请人：——

  公开号：US8252841B2

  公开（公告）日：2012-08-28
• New 2H-chromene-3-carboxamide derivatives: Design, synthesis and use as inhibitors of hMAO
  作者：Zhi-Xiang Pan、Xu He、Yan-Yan Chen、Wen-Jian Tang、Jing-Bo Shi、Yu-Lan Tang、Bao-An Song、Jun Li、Xin-Hua Liu

  DOI：10.1016/j.ejmech.2014.04.060

  日期：2014.6

  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.