4-azido-2-oxo-2H-chromene-3-carbaldehyde | 136806-16-1

• 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: 4-azido-2-oxo-2H-chromene-3-carbaldehyde
• 英文别名: 4-azido-3-formylcoumarin；4-azido-2-oxochromene-3-carbaldehyde
• CAS: 136806-16-1
• 化学式: C₁₀H₅N₃O₃
• 分子量: 215.168
• InChiKey: ZTPMOUVMPVFYEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-azido-2-oxo-2H-chromene-3-carbaldehyde 在 异硫氰酸乙酯 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到2-oxo-4-(thioxoamino)-2H-chromene-3-carbaldehyde
  参考文献：
  名称：

  The Behavior of 4-Azidocoumarin-3-carboxaldehyde Towards Certain Sulfur Reagents and Primary Amines

  摘要：

  The behavior of 4-azidocoumarin-3-carboxaldehyde (1) towards certain sulfur reagents such as isothiocyanates (2a-c), thionyl chloride, Lawesson's reagent (LR, 3), and phosphorus pentasulfide as well as towards primary amines such as glycine (4) and towards anthranilic acid (5) was investigated. The structures of the new products were attested by suitable analytical and spectroscopic measurements.

  DOI：

  10.1080/10426500902855133
• 作为产物：
  描述：

  4-氯-3-甲酰基香豆素 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 以74%的产率得到4-azido-2-oxo-2H-chromene-3-carbaldehyde
  参考文献：
  名称：

  Steinfuehrer, Thorsten; Hantschmann, Achim; Pietsch, Michael, Liebigs Annalen der Chemie, 1992, # 1, p. 23 - 28

  摘要：

  DOI：

文献信息

• Substituted coumarin amidines: useful building blocks for the preparation of [1]benzopyrano[4,3-b]pyridin-5-one and [1]benzopyrano[4,3-d]pyrimidin-5-one derivatives
  作者：Egle M. Beccalli、Alessandro Contini、Pasqualina Trimarco

  DOI：10.1016/j.tet.2005.03.050

  日期：2005.5

  synthesis of [1]benzopyrano[4,3-b]pyridin-5-ones 4a–f and 4g–j starting from 3-formylcoumarin and 3-cyanocoumarin N-functionalized amidines 3a–f and 3g–j, respectively, was reported. The ring-closure reaction mechanism, under basic or acidic media, was proposed. Furthermore, the reaction of 3-formylamidines 3a,c–f with ammonium acetate gave good yields of 2-substituted [1]benzopyrano[4,3-d]pyrimidin-5-ones

  的[1]苯并吡喃并[4,3-合成b ]吡啶-5-酮4A - ˚F和4克- Ĵ从3- formylcoumarin和3-氰基香豆素起始ñ -官能化脒3A - ˚F和3克- Ĵ，分别是报告。提出了在碱性或酸性介质下的闭环反应机理。此外，3-甲酰idine3a，c - f与乙酸铵的反应产生了2-取代的[1]苯并吡喃并[4,3 - d ]嘧啶-5-酮7的良好收率。
• New phosphazine and phosphazide derivatives as multifunctional ligands targeting acetylcholinesterase and β-Amyloid aggregation for treatment of Alzheimer's disease
  作者：Naglaa F. El-Sayed、Marwa El-Hussieny、Ewies F. Ewies、Marwa A. Fouad、Leila S. Boulos

  DOI：10.1016/j.bioorg.2019.103499

  日期：2020.1

  Phosphazine and phosphazide derivatives are described herein as a new class of selective and potent acetylcholinesterase (AChE) inhibitors and β-amyloid aggregation inhibitors. Phosphazines (5-7) were synthesized smoothly via a redox-condensation reaction of 1,2-bis(diphenylphosphino)ethane with different amines derivatives in the presence of dialkyl azodicarboxylate (Staudinger reaction) while phosphazides

  膦嗪和磷腈衍生物在本文中被描述为一类新型的选择性和有效的乙酰胆碱酯酶（AChE）抑制剂和β-淀粉样蛋白聚集抑制剂。在偶氮二羧酸二烷基酯存在下，1,2-双（二苯基膦基）乙烷与不同的胺衍生物进行氧化还原缩合反应（斯托丁格反应），而磷叠氮化物（8）则通过叠氮衍生物的亲电攻击而平稳地合成了磷嗪（5-7）。 。根据相容的元素分析和光谱分析，证明了合成化合物的结构是正确的。评价所有化合物的乙酰胆碱酯酶抑制活性。最强的三种化合物（5b-c和8b）的AChE IC50值（29.85-34.96 nM）与多奈哌齐（34。42 nM）通过测试其丁酰胆碱酯酶，MMP-2和自诱导的Aβ聚集抑制活性进行进一步研究。尤其是，香豆素磷腈衍生物（8b）表现出最佳的AChE抑制选择性指数（IC50 = 34.96 nM，AChE / BuChE; 3.81）以及对MMP-2的良好抑制能力（IC50 = 441.33 nM）和自诱导的Aβ1-42聚集（IC50
• New synthetic approach to [1]benzopyrano[4,3-b]pyridin-5-one derivatives
  作者：Egle M. Beccalli、Alessandro Contini、Pasqualina Trimarco

  DOI：10.1016/j.tetlet.2004.03.009

  日期：2004.4

  A new synthesis of [1]benzopyrano[4,3-b]pyridin-5-ones 4 was developed starting from 3-formyl-coumarin N-functionalized amidines 3. The reaction is based likely on the intramolecular cyclocondensation of the C-α amidinic carbanion in basic medium on the formyl group.

  从3-甲酰基香豆素N-官能化am 3开始，开发了[1]苯并吡喃并[4,3 - b ]吡啶-5-酮4的新合成方法。该反应很可能是基于在甲酰基的碱性介质中C-α氨基碳负离子的分子内环缩合。
• Chemistry of Phosphonium Ylides. Part 39: Facile Synthesis of Aziridine, Pyridine, Pyrolotriazole Chromenones and Azaphosphinin Chromenones as Antitumor Agents
  作者：Mansoura A. Abd-El-Maksoud、Soher S. Maigali、Fouad M. Soliman

  DOI：10.1002/jhet.2205

  日期：2014.11

  ne‐3‐carbaldehyde with the active nucleophilic phosphacumulenes yielded the corresponding phosphanylidene‐aziridines and chromeno‐pyrolo‐triazoles. On the other hand, the reaction of the allylic phosphonium ylide, hexaphenylcarbodiphosphorane with the azido compound, was also undertaken. In this case, the phosphanylidene‐chromeno‐triazinone was obtained. Further assessment of these new compounds against

  4－叠氮基－2－氧代-2- H－色烯－3－甲醛与活性亲核性磷原子的反应生成了相应的膦亚基-氮丙啶和苯并吡咯并三唑。另一方面，还进行了烯丙基磷鎓内鎓盐六苯基碳二膦与叠氮基化合物的反应。在这种情况下，获得了膦亚基-铬基-三嗪酮。有必要对这些新化合物针对（乳腺癌：MCF-7和肝脏：HPEG2）人实体瘤细胞系进行评估。
• Synthesis of Novel Coumarin Derivatives Bearing Phosphor Ester Motifs and Evaluation of their Antioxidant Activities
  作者：Maha Khidre、Eman Sabry、Abdel-Tawab Mossa、Abeer Shaddy

  DOI：10.21608/ejchem.2020.31702.2676

  日期：2020.7.8

  triamide derivatives were obtained via Staudinger reaction. Contrary to that pathway, phosphoranylidenetriazen chromen derivative could be isolated and identified when coumarin 16 was allowed to react with tris(diethylamino)-phosphine. The antioxidant activities of 6-newly products were evaluated. The results showed that two from the six screened compounds exhibited good antioxidant activities.

  当取代的阿齐多香豆素1与三烷基亚磷酸酯（TAP），二烷基膦酸酯（DAP）和三（二烷基氨基）膦反应时，可以分别形成氨基磷酸酯，亚磷酰胺基氮杂氮杂和氮杂磷酰基衍生物。揭示了已知的三嗪二酮是甲醛1与TAP和三（二烷基氨基）-膦反应的副产物。在相同的情况下，当使起始香豆素16与P（III）试剂反应时，通过施陶丁格反应获得了亚磷酸铬氨基酯和亚磷酸三酰胺铬衍生物。与该途径相反，当香豆素16与三（二乙氨基）膦反应时，可以分离并鉴定出磷酰亚内酯基铬衍生物。评价了6种新产品的抗氧化活性。