3-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-chromen-2-one | 144616-89-7

• 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: 3-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-chromen-2-one
• 英文别名: 3-[(4-Methoxyphenyl)methylideneamino]chromen-2-one
• CAS: 144616-89-7
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: GXNWYCAZLIPFLM-UHFFFAOYSA-N

物化性质

• 沸点：
  479.8±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 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：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-chromen-2-one 、 methyl 1-benzyl-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate 在 ytterbium(III) triflate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以0.49 g的产率得到methyl 1-benzyl-5-(4-methoxyphenyl)-2-methyl-7-oxo-4-phenyl-4,4a,5,6,7,12c-hexahydro-1H-chromeno[3,4-h][1,6]naphthyridine-3-carboxylate
  参考文献：
  名称：

  Exploration of C5–C6-Unsubstituted 1,4-Dihydropyridines for the Construction of exo-Hexahydro-1H-chromeno[3,4-h][1,6]naphthyridine-3-carboxylates Using a Stereoselective Povarov Reaction

  摘要：

  A wide variety of substituted exo-hexahydro-1H-chromeno[3,4-h][1,6]naphthyridine-3-carboxylate derivatives have been synthesized from 3-aminocoumarins, aldehydes, and 5,6-unsubstituted 1,4-dihydropyridine derivatives in the presence of 10 mol% of ytterbium(III) triflate in acetonitrile at room temperature using a one-pot Povarov reaction. Some of the salient features of this protocol are: good yields and no need for an aqueous workup procedure or chromatographic separation.

  DOI：

  10.1055/s-0034-1380431
• 作为产物：
  描述：

  3-氨基香豆素 、 4-甲氧基苯甲醛 在 乙酸酐 作用下， 以 乙醇 为溶剂， 以58%的产率得到3-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-chromen-2-one
  参考文献：
  名称：

  3-（苄叉基氨基）香豆素在啮齿动物中的合成及抗炎活性。

  摘要：

  合成了一系列取代的3-（亚苄基氨基）香豆素，并评价了对角叉菜胶诱发的大鼠水肿的抗炎活性。口服剂量为100 mg / kg的卤代衍生物4g和4c分别显示出75％和60％的抗浮肿活性（苯基丁a的抗浮肿活性为58％）。4g和4c的镇痛活性基于乙酸对小鼠扭体的抑制作用（口服剂量100 mg / kg分别为67％和62％）与阿司匹林（58％）相当。但是，这些衍生物没有解热活性，并且对佐剂诱导的关节炎的活性较低。

  DOI：

  10.1002/jps.2600810926

文献信息

• 香豆素类化合物及其制备方法和应用
  申请人：新疆农业大学

  公开号：CN117720496A

  公开（公告）日：2024-03-19

  本发明公开了香豆素类化合物及其制备方法和应用。本发明的香豆素类化合物选自式(A‑A)所示的化合物；#imgabs0#其中，所述R1选自#imgabs1#所示的基团、H或C1‑C10烷基，其中R1′选自H或C1‑C10的草酰氯酯、R1”选自取代或未取代的芳基；所述R2选自#imgabs2#所示的基团或H，其中R2′选自取代或未取代的芳基；所述R3选自#imgabs3#所示的基团、H或羟基，其中R3′选自C1‑C10羧酸、R3”选自取代或未取代的芳基；且所述香豆素类化合物的R1中选自氢时，R3不能选自羟基。本发明的香豆素类化合物结构简单，分子量小；有较好的生物活性，对测试菌均有不同程度抑制，可作为潜在的新型抗菌剂。
• Novel Aminocoumarin Derivatives against Phytopathogenic Fungi: Design, Synthesis and Structure‐Activity Relationships
  作者：Pengzhi Sun、Jiangping Pu、Dongyu Lei、Jiashan Li、Xingyu Ren、Lu Jin、Le Pan

  DOI：10.1002/cbdv.202400311

  日期：2024.5

  Phytopathogenic fungi is the most devastating reason for the decrease of the agricultural production and food safety. To develop new fungicidal agents for resistance concerning, a novel series of aminocoumarin derivatives were synthesized and their fungicidal activity were investigated both in vitro and in vivo. Transmission electron microscope (TEM), scanning electron microscope (SEM), RNA‐Seq, 3D‐QSAR and molecular docking were applied to reveal the underlying anti‐fungal mechanisms. Most of the compounds exhibited significant fungicidal activity. Notably, compound 10c had a more extensive fungicidal effect than positive control. TEM indicated that compound 10c could cause abnormal morphology of cell walls, vacuoles and release of cellular contents. Transcriptional analysis data indicated that 895 and 653 out of 1548 differential expressed genes (DEGs) were up‐regulated and down‐regulated respectively. The Go and KEGG enrichment indicated that the coumarin derivatives could induce significant changes of succinate dehydrogenase (SDH), Acetyl‐coenzyme A synthetase (ACCA) and pyruvate dehydrogenase (PDH) genes, which contributed to the disorders of glucolipid metabolism and the dysfunction of mitochondrial. The results demonstrated that aminocoumarins with schiff‐base as core moieties could be the promising lead compounds for the discovery of novel fungicides.