2-amino-4-(4-methylsulfanylphenyl)-3-cyano-5-oxo-4H,5H,-pyrano[3,2-c]chromene | 331951-06-5

• 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: 2-amino-4-(4-methylsulfanylphenyl)-3-cyano-5-oxo-4H,5H,-pyrano[3,2-c]chromene
• 英文别名: 2-amino-4-[4-(methylsulfanyl)phenyl]-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile；2-amino-4-(4-methylsulfanylphenyl)-5-oxo-4H-pyrano[3,2-c]chromene-3-carbonitrile
• CAS: 331951-06-5
• 化学式: C₂₀H₁₄N₂O₃S
• 分子量: 362.409
• InChiKey: UDCMGZACIRXGNN-UHFFFAOYSA-N

物化性质

• 沸点：
  674.9±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 4-(甲基巯基)苯甲醛 、 丙二腈 在 4-二甲氨基吡啶 作用下， 以 乙醇 为溶剂， 以79%的产率得到2-amino-4-(4-methylsulfanylphenyl)-3-cyano-5-oxo-4H,5H,-pyrano[3,2-c]chromene
  参考文献：
  名称：

  Evaluation of Antibacterial Activities of 4-Hydroxycoumarin Derivatives

  摘要：

  摘要：合成了三种4-羟基香豆素衍生物，分别为双香豆素（1-4）、环氧双香豆素（5-8）和二氢吡喃（9-12），并评估了它们的抗菌活性。初步生物测定结果显示，化合物1和2对药物敏感型金黄色葡萄球菌（ATCC 29213）和耐甲氧西林金黄色葡萄球菌（MRSA XJ 75302、Mu50、ATCC 700699和USA 300）的最低最小抑制浓度（MIC）为4-64 ug/mL。此外，双香豆素（1-4）的结构中存在两个经典的分子内O—H⋯O氢键（HBs），并且它们的对应HB能量进一步通过密度泛函理论（DFT）[B3LYP/6-31G*]方法计算。

  DOI：

  10.1515/zpch-2015-0630

文献信息

• Imidazole as organocatalyst for multicomponent reactions: diversity oriented synthesis of functionalized hetero- and carbocycles using in situ-generated benzylidenemalononitrile derivatives
  作者：Md. Nasim Khan、Suman Pal、Shaik Karamthulla、Lokman H. Choudhury

  DOI：10.1039/c3ra45252b

  日期：——

  The multicomponent reaction of malononitrile, aldehyde and a third reaction partner such as naphthol/4-hydroxycoumarine/2-hydroxynaphthoquinone/kojic acid/enolizable ketone or thiol in the presence of imidazole as an organocatalyst provides very interesting molecular diversity. In an almost neutral reaction medium, this protocol provides easy access to highly functionalized 2-amino-4H-chromenes, dienes and 2-amino pyridines using in situ-generated aryl/alkylylidenemalononitrile derivatives obtained from the reaction of aldehydes and malononitrile along with various nucleophiles under reflux conditions in ethanol. This methodology is useful for the easy access of a wide range of structurally diverse functionalized molecules having potential application in biological systems.

  咪唑作为有机催化剂存在下，丙二腈、醛和一个第三反应伙伴（如萘酚、4-羟基香豆素、2-羟基萘醌、曲酸、可烯醇化的酮或硫醇）的多组分反应提供了非常有趣的分子多样性。在近乎中性的反应介质中，该方案通过在乙醇中回流条件下由醛和丙二腈反应生成的原位生成的芳基/烷基亚甲基丙二腈衍生物与各种亲核试剂的反应，易于制备高度官能化的2-氨基-4H-色烯、二烯和2-氨基吡啶。这种方法有助于轻松获得结构多样、具有潜在生物应用价值的官能化分子。
• 2‐Amino‐4‐aryl‐5‐oxo‐4,5‐dihydropyrano[3,2‐ <i>c</i> ]chromene‐3‐carbonitriles with Microtubule‐Disruptive, Centrosome‐Declustering, and Antiangiogenic Effects <i>in vitro</i> and <i>in vivo</i>
  作者：Leonhard H. F. Köhler、Sebastian Reich、Gerrit Begemann、Rainer Schobert、Bernhard Biersack

  DOI：10.1002/cmdc.202200064

  日期：2022.5.18

  AbstractA series of fifteen 2‐amino‐4‐aryl‐5‐oxo‐4,5‐dihydropyrano[3,2‐c]chromene‐3‐carbonitriles (1 a–o) were synthesized via a three‐component reaction of 4‐hydroxycoumarin, malononitrile, and diversely substituted benzaldehydes or pyridine carbaldehydes. The compounds were tested for anticancer activities against a panel of eight human tumor cell lines. A few derivatives with high antiproliferative activities and different cancer cell specificity were identified and investigated for their modes of action. They led to microtubule disruption, centrosome de‐clustering and G2/M cell cycle arrest in 518 A2 melanoma cells. They also showed anti‐angiogenic effects in vitro and in vivo.