N-(4-甲氧基苯基)香豆素-3-甲酰胺 | 1846-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-甲氧基苯基)香豆素-3-甲酰胺
• 英文名称: N-(4-methoxyphenyl)-2-oxo-2H-chromene-3-carboxamide
• 英文别名: N-(4-methoxyphenyl)-2-oxochromene-3-carboxamide
• CAS: 1846-94-2
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: UVIDYPCYACCLOZ-UHFFFAOYSA-N

物化性质

• 熔点：
  269-270 °C
• 沸点：
  566.6±50.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  N-(4-甲氧基苯基)香豆素-3-甲酰胺 在 palladium on activated charcoal 作用下， 以 xylene 为溶剂， 反应 30.5h， 生成 6H-5-Oxabenzanthracen-6-on
  参考文献：
  名称：

  合成和新[4 + 2]-环加成反应物vonCumarin-Abkömmlingen

  摘要：

  死SYNTHESE sowie模具physikalischen Eigenschaften DER香豆素Abkömmlinge 5A - d，7α - d UND 11 AUS巢穴Azomethinen 1A - d UND 6A - d werden beschrieben。第三人以thermische Umsetzung冯5B - d奥德7B MIT 2,3-二甲基-1,3-丁二烯werden模具neuen Cycloaddukte 12A - Ç bzw. 13 gebildet，während图5c，d奥德7B MIT 1,2-双（亚甲基）环己模具Polycyclen 15A，bbzw。14 ergeben。

  DOI：

  10.1002/jlac.198519850504
• 作为产物：
  描述：

  2-((4-甲氧基苯亚氨基)甲基)苯酚 在 溶剂黄146 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 53.0h， 生成 N-(4-甲氧基苯基)香豆素-3-甲酰胺
  参考文献：
  名称：

  Bonsignore, Leonardo; Cabiddu, Salvatore; Loy, Giuseppe, Heterocycles, 1984, vol. 22, # 11, p. 2587 - 2590

  摘要：

  DOI：

文献信息

• Design, synthesis and antifungal activity evaluation of coumarin-3-carboxamide derivatives
  作者：Xiang Yu、Peng Teng、Ya-Ling Zhang、Zhao-Jun Xu、Ming-Zhi Zhang、Wei-Hua Zhang

  DOI：10.1016/j.fitote.2018.03.013

  日期：2018.6

  A series of coumarin-3-carboxamides/hydrazides have been designed and synthesized, all the target compounds were evaluated in vitro for their antifungal activity against Botrytis cinerea, Alternaria solani, Gibberella zeae, Rhizoctorzia solani, Cucumber anthrax and Alternaria leaf spot, some of the designed compounds 4a-4g exhibited potential activity in the primary assays, this highlighted by the

  设计并合成了一系列香豆素-3-羧酰胺/酰肼，体外评估了所有目标化合物对灰霉病菌，链格孢菌，玉米赤霉菌，索氏根瘤菌，黄瓜炭疽和链霉菌叶斑的抗真菌活性。设计的化合物4a-4g在主要试验中表现出潜在的活性，这在化合物4a，4d，4e和4f中得到了突出显示，其对茄枯菌的EC50值低至1.80μg/ mL，2.50μg/ mL，2.25μg / mL和2.10μg/ mL分别显示出比Boscalid更有效的对照。此外，化合物4a和4e与Boscalid对灰葡萄孢的抗真菌活性相当。
• 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。
• Cyclopropanation of N-Substituted 2-Oxochromene- and 6-Bromo-2-oxochromene-3-carboxamides with Zinc Enolates Derived from 1-Aryl-2,2-dibromoalkanones
  作者：V. V. Shchepin、P. S. Silaichev、R. V. Shchepin、M. A. Ezhikova、M. I. Kodess

  DOI：10.1007/s11178-005-0199-6

  日期：2005.4

  Zinc enolates derived from 1-aryl-2,2-dibromoalkanones react with N-cyclohexyl-2-oxochromene-3-carboxamides to give N-cyclohexyl-1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides mainly as cis isomers with respect to the substituents in positions 1 and 1a. Reactions of the same zinc enolates with N-benzyl-2-oxochromene-3-carboxamide and N-benzyl-6-bromo-2-oxochromene-3-carboxamide lead to formation of 1-aryl-2-benzyl- and 1-aryl-2-benzyl-6-bromo-1-hydroxy-9c-alkyl-1,2,9b,9c-tetrahydro-5-oxa-2-azacyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones. The reaction of zinc enolates with N-aryl-2-oxochromene-3-carboxamides in a weakly polar solvent (diethyl ether or ethyl acetate) affords mixtures of cis-N-aryl-1-aroyl-1-alkyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides and their cyclic isomers, 9c-alkyl-1,2-diaryl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-azacyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones, the latter prevailing. N-Substituted 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides in which the aroyl group on C1 and the carboxamide group on C1a are arranged trans are formed by reactions of zinc enolates with the corresponding 2-oxochromene-3-carboxamides in the presence of hexamethylphosphoric triamide.

  源自1-芳基-2,2-二溴代烷基酮的锌烯醇盐与N-环己基-2-氧代色烯-3-羧酰胺反应，主要生成顺式异构体，相对于位置1和1a的取代基，形式为N-环己基-1-烷基-1-芳酰基-2-氧代-1a,7b-二氢环丙[c]色烯-1a-羧酰胺。同样的锌烯醇盐与N-苄基-2-氧代色烯-3-羧酰胺和N-苄基-6-溴-2-氧代色烯-3-羧酰胺反应，生成1-芳基-2-苄基和1-芳基-2-苄基-6-溴-1-羟基-9c-烷基-1,2,9b,9c-四氢-5-氧-2-氮杂环戊[2,3]环丙[1,2-a]萘-3,4-二酮。锌烯醇盐与N-芳基-2-氧代色烯-3-羧酰胺在弱极性溶剂（乙醚或乙酸乙酯）中反应，得到顺式N-芳基-1-芳酰基-1-烷基-2-氧代-1a,7b-二氢环丙[c]色烯-1a-羧酰胺及其环状异构体，即9c-烷基-1,2-二芳基-1-羟基-1,2,9b,9c-四氢-5-氧-2-氮杂环戊[2,3]环丙[1,2-a]萘-3,4-二酮，后者占优势。在六甲基磷酸三胺存在下，锌烯醇盐与相应的2-氧代色烯-3-羧酰胺反应，生成N-取代的1-烷基-1-芳酰基-2-氧代-1a,7b-二氢环丙[c]色烯-1a-羧酰胺，其中C1上的芳酰基和C1a上的羧酰胺基团以反式排列。
• 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。
• Lanthanum(III)-Catalyzed Three-Component Reaction of Coumarin-3-carboxylates for the Synthesis of Indolylmalonamides and Analysis of Their Photophysical Properties
  作者：Julia J. Jennings、Chinmay P. Bhatt、Annaliese K. Franz

  DOI：10.1021/acs.joc.6b00541

  日期：2016.8.5

  First, the scandium(III)-catalyzed addition of diverse nucleophiles (e.g., indoles, N,N-dimethyl-m-anisidine, 2-ethylpyrrole, and 2-methylallylsilane) to coumarin-3-carboxylates has been developed to afford chromanone-3-carboxylates in high yields as a single diastereomer. Upon investigating a subsequent lanthanum(III)-catalyzed amidation reaction, a new multicomponent reaction was designed by bringing

  已经开发了用于路易斯酸催化的丙二酰胺合成的新方法。首先，the（III）催化添加各种亲核试剂（例如吲哚，N，N-二甲基-m-苯甲醚，2-乙基吡咯和2-甲基烯丙基硅烷）生成香豆素3-羧酸盐，以高收率得到单价非对映异构体的苯并二氢吡喃酮3-羧酸盐。在研究了随后的镧（III）催化的酰胺化反应后，通过将香豆素3-羧酸盐与吲哚和胺混合在一起，设计了一种新的多组分反应，从而得到了吲哚基丙二酰胺，这些化合物被证明具有荧光特性。分析了所选化合物的光物理性质，包括量子产率，摩尔吸收率和斯托克斯位移。对三组分反应的反应平衡网络中涉及的几种反应副产物的综合研究为该方法的发展提供了机械学的见解。