2-amino-4-(3,4-dichlorophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile | 293759-04-3

• 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-(3,4-dichlorophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile
• 英文别名: 2-amino-4-(3,4-dichlorophenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene；2-amino-4-(3,4-dichlorophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile；2-amino-4-(3,4-dichlorophenyl)-5-oxo-4H-pyrano[3,2-c]chromene-3-carbonitrile
• CAS: 293759-04-3
• 化学式: C₁₉H₁₀Cl₂N₂O₃
• 分子量: 385.206
• InChiKey: AIWKGPDVGPWXCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 2-(3,4-dichlorobenzylidene)malononitrile 在 potassium fluoride 、 Montmorillonite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以86%的产率得到2-amino-4-(3,4-dichlorophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile
  参考文献：
  名称：

  Synthesis of 2-Amino-4-Aryl-5-Oxo-4,5-Dihydropyrano[3,2-c] Chromene Derivatives Catalysed by KF-Montmorillonite

  摘要：

  在 KF-蒙脱石的催化下，4-羟基香豆素和取代的肉桂醛发生反应，合成了一系列 2-氨基-4-芳基-5-氧代-4,5-二氢吡喃并[3,2-c]色烯衍生物。通过红外光谱和 1H NMR 光谱数据对其结构进行了表征，并通过 X 射线衍射分析对其进行了确认。

  DOI：

  10.3184/030823408x347585

文献信息

• Evaluation of Antibacterial Activities of 4-Hydroxycoumarin Derivatives
  作者：Yue Hu、Jing Li、Chang-Wei Lv、Di Qu、Zheng Hou、Min Jia、Jiang-Tao Li、Zi-Dan Zhang、Xiao-Xing Luo、Zhi Yuan、Ming-Kai Li

  DOI：10.1515/zpch-2015-0630

  日期：2016.1.28

  Three kinds of 4-hydroxycoumarin derivatives, namely, biscoumarins (1–4), epoxydicoumarins (5–8) and dihydropyrans (9–12), were synthesized and the antibacterial activity of each of them was evaluated. The result of preliminary bioassay shows that the lowest minimal inhibitory concentration (MIC) of compounds 1 and 2 against drug-sensitive S. aureus (ATCC 29213) and methicillin-resistant S. aureus (MRSA XJ 75302, Mu50, ATCC 700699 and USA 300) is 4–64 ug/mL. Additionally, there are two classical intramolecular O—H⋯O hydrogen bonds (HBs) in the structures of biscoumarins (1–4), and their corresponding HB energies were further calculated by the density functional theory (DFT) [B3LYP/6-31G*] method.

  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。
• Highly efficient three-component, one-pot synthesis of dihydropyrano[3,2-c]chromene derivatives
  作者：Hong-Juan Wang、Jie Lu、Zhan-Hui Zhang

  DOI：10.1007/s00706-010-0383-4

  日期：2010.10

  AbstractAn efficient and convenient method for synthesis of dihydropyrano[3,2-c]chromene derivatives by one-pot, three-component reaction of aldehydes, malononitrile, and 4-hydroxycoumarin in the presence of a catalytic amount of hexamethylenetetramine is reported. A variety of dihydropyrano[3,2-c]chromene derivatives were obtained in high to excellent yields within short times. Graphical abstract

  摘要据报道，在催化量的六亚甲基四胺存在下，通过醛，丙二腈和4-羟基香豆素的一锅三组分反应，合成二氢吡喃并[3,2- c ]亚甲基苯衍生物的有效方法。在短时间内以高产率至优异产率获得了多种二氢吡喃并[3，2- c ]亚甲基苯衍生物。 图形概要
• Synthesis of a novel piperidine-functionalized poly(ethylene glycol) bridged dicationic ionic liquid and its application in one-pot synthesis of substituted 2-amino-2-chromenes and 3,4-dihydropyrano[3,2-c]chromenes in aqueous media
  作者：Yinglei Wang、Jun Luo、Tantan Xing、Zuliang Liu

  DOI：10.1007/s00706-013-1066-8

  日期：2013.12

  AbstractA novel piperidine-functionalized poly(ethylene glycol) bridged dicationic ionic liquid was prepared and identified. It was used as a recyclable catalyst for the synthesis of substituted 2-amino-2-chromenes and 3,4-dihydropyrano[3,2-c]chromenes with excellent yields through a one-pot three-component reaction of aromatic aldehydes, malononitrile, and activated phenols in aqueous media. This

  摘要制备并鉴定了新颖的哌啶官能化的聚乙二醇桥联的双离子型离子液体。通过芳香族醛，丙二腈的一锅式三组分反应，以优异的收率将其用作可回收的催化剂，用于合成取代的2-氨基-2-色烯和3,4-二氢吡喃并[3,2- c ]色烯。以及水性介质中的活化酚。发现这种对环境无害的协议相当有效，并提供了广泛的基板灵活性。碱性离子液体可以重复使用几次，而不会明显降低催化活性。 图形概要
• In vitro anticancer activity of pyrano[3, 2-c]chromene derivatives with both cell cycle arrest and apoptosis induction
  作者：Ahmed M. El-Agrody、Ahmed M. Fouda、Mohammed A. Assiri、Ahmed Mora、Tarik E. Ali、Mohammed M. Alam、Mohammad Y. Alfaifi

  DOI：10.1007/s00044-019-02494-3

  日期：2020.4

  excellent antitumor activity versus all cancer cell lines with IC50 values ranging from 0.2 to 1.7 μM. The cell cycle arrest behavior of compounds 4e, 4f, and 4m was investigated. The results illustrated that the potent cytotoxic compounds 4e, 4f, and 4m induce cell cycle arrest at the G2/M phases and trigger apoptosis in the different tested cancer cells. Finally, the structure activity relationship

  通过一锅三组分之间的一锅三组分缩合反应合成了一系列2-氨基-4-芳基-5-氧代-4,5-二氢吡喃[3,2- c ]亚甲基-3-腈（4a – m）。在微波辐射条件下，在乙醇中以哌啶为催化剂，在乙醇中以-羟基-2- H-铬-2--2-酮，各种芳基醛和丙二腈的收率好至极好。所有合成化合物的结构解析均通过光谱数据，红外光谱，1 H NMR，1313 C NMR，MS和元素分析。使用磺基罗丹明B测定（SRB）方法评估了目标化合物对乳腺乳腺癌细胞系（MCF-7），人结肠癌（HCT-116）和肝癌（HepG-2）的体外抗癌活性，将阿霉素用作标准参考药物。用合成化合物以不同剂量处理癌细胞，并测定细胞活力。与所有癌细胞系相比，化合物4e，4f和4m表现出优异的抗肿瘤活性，IC 50值为0.2至1.7μM。化合物4e，4f和4m的细胞周期停滞行为被调查了。结果表明，有效的细胞毒性化合物4e，4f和4m诱导了G2
• 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.