2-amino-5-oxo-4-(3,4,5-trimethoxyphenyl)-4H,5H-pyrano[3,2-c]chromene-3‑carbonitrile | 293329-72-3

• 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-5-oxo-4-(3,4,5-trimethoxyphenyl)-4H,5H-pyrano[3,2-c]chromene-3‑carbonitrile
• 英文别名: 2-amino-4-(3,4,5-trimethoxyphenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile；2-amino-5-oxo-4-(3,4,5-trimethoxyphenyl)-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile；2-amino-5-oxo-4-(3,4,5-trimethoxyphenyl)-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile；2-amino-4-(3,4,5-trimethoxyphenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene；2-amino-5-oxo-4-(3,4,5-trimethoxyphenyl)-4H-pyrano[3,2-c]chromene-3-carbonitrile
• CAS: 293329-72-3
• 化学式: C₂₂H₁₈N₂O₆
• 分子量: 406.395
• InChiKey: UKTFMPQSNSFGKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-amino-5-oxo-4-(3,4,5-trimethoxyphenyl)-4H,5H-pyrano[3,2-c]chromene-3‑carbonitrile 在 溶剂黄146 作用下， 生成 1,2-benzo-[1,3-diaza-4-(4-methoxyaniline)-5-(3,4,5-trimethoxyphenyl)-6-oxo-7,10-dioxa]anthracene
  参考文献：
  名称：

  作为黄嘌呤氧化酶抑制剂的稠合吡喃并[3,2-d]嘧啶衍生物的合成，筛选和对接。

  摘要：

  鉴于开发有效的黄嘌呤氧化酶（XO）酶抑制剂，合成了一系列100种吡喃并[3,2-d]嘧啶衍生物，并对其体外XO酶抑制进行了评估。结构活动关系也已建立。在所有合成的化合物中，发现4d，8d和9d是最有效的酶抑制剂，IC50值分别为8μM，8.5μM和7μM。在酶动力学研究中进一步研究了化合物9d，Lineweaver-Burk图显示化合物9d是混合型抑制剂。还已经计算出最有效的化合物4d，8d和9d的分子性质。进行了对接研究以研究黄嘌呤氧化酶与最有效的XO抑制剂9d之间的识别模式。

  DOI：

  10.1016/j.ejmech.2017.03.002
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 (2-aminomethyl)phenol moiety on the surface of hydroxyapatite encapsulated maghemite (γ-Fe₂O₃) 作用下， 以 水 为溶剂， 反应 0.08h， 生成 2-amino-5-oxo-4-(3,4,5-trimethoxyphenyl)-4H,5H-pyrano[3,2-c]chromene-3‑carbonitrile
  参考文献：
  名称：

  Design, synthesis, docking study and biological evaluation of some novel tetrahydrochromeno [3′,4′:5,6]pyrano[2,3-b]quinolin-6(7H)-one derivatives against acetyl- and butyrylcholinesterase

  摘要：

  Novel hybrid derivatives of two known scaffolds; tetrahydroaminoquinoline and coumarin were synthesized and evaluated for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) activities. By means of an efficient nanocatalyst, the reaction time for the syntheses of the target compounds was reduced. Subsequently, Ellman's modified method was used to evaluate the enzyme inhibitory activity of the synthesized structures. It was observed that most hybrid structures were moderate to potent inhibitors of AChE compared to Tacrine as the reference drug among which 7f with 4-fluorophenyl substituent was the most active compound (IC50 = 5 nM). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.045

文献信息

• A green one-pot three-component synthesis of tetrahydrobenzo[b]pyran and 3,4-dihydropyrano[c]chromene derivatives using a Fe₃O₄@SiO₂–imid–PMAⁿ magnetic nanocatalyst under ultrasonic irradiation or reflux conditions
  作者：Mohsen Esmaeilpour、Jaber Javidi、Farzaneh Dehghani、Fatemeh Nowroozi Dodeji

  DOI：10.1039/c5ra01021g

  日期：——

  An efficient and environmentally benign procedure for the synthesis of tetrahydrobenzo[b]pyran and 3,4-dihydropyrano[c]chromene derivatives has been developed by a one-pot three-component reaction of various aldehydes, malononitrile, and dimedone or hydroxycoumarin in the presence of Fe3O4@SiO2–imid–PMAn nanoparticles as magnetic catalysts under ultrasonic irradiation or reflux conditions in water

  通过在锅中各种醛，丙二腈，二甲酮或羟基香豆素的一锅三组分反应，开发了一种有效的，对环境无害的合成四氢苯并[ b ]吡喃和3,4-二氢吡喃并[ c ]色烯衍生物的方法。 Fe 3 O 4 @SiO 2-亚胺基-PMA n的存在超声辐射或水中回流条件下，纳米颗粒作为磁性催化剂。该新方法具有显着的优点，例如操作简单，产率高，反应时间短以及无需任何繁琐的后处理或纯化。另外，在水介质中的优异催化性能以及催化剂的易于制备，热稳定性和分离使其成为良好的非均相体系，并且是其他非均相催化剂的有用替代品。同样，该催化剂可以很容易地通过磁场回收并在连续的八个反应循环中重复使用而没有明显的活性损失。
• Tris-hydroxymethylaminomethane (THAM): a novel organocatalyst for a environmentally benign synthesis of medicinally important tetrahydrobenzo[b]pyrans and pyran-annulated heterocycles
  作者：Kapil S. Pandit、Pramod V. Chavan、Uday V. Desai、Makarand A. Kulkarni、Prakash P. Wadgaonkar

  DOI：10.1039/c4nj02346c

  日期：——

  A simple, efficient and environmentally benign protocol has been developed for the one-pot, multicomponent synthesis of medicinally important tetrahydrobenzo[b]pyrans and pyran-annulated heterocycles using a commercially available, inexpensive, non-toxic, and biodegradable tris-hydroxymethylaminomethane (THAM) as a novel organocatalyst. Ambient reaction conditions, wide scope, avoidance of conventional

  已经开发了一种简单，有效且对环境无害的方案，用于使用市售，廉价，无毒且可生物降解的三羟甲基甲基甲烷（THAM）一锅，多组分合成重要的药用四氢苯并[ b ]吡喃和吡喃环杂环）作为新型有机催化剂。环境反应条件，宽范围，避免常规分离以及纯化技术以及催化剂连续五次运行的可重复使用性提高了该多组分反应规程歧管的实用性。
• Synthesis of new low-viscous sulfonic acid-functionalized ionic liquid and its application as a Brönsted liquid acid catalyst for the one-pot mechanosynthesis of 4H-pyrans through the ball milling process
  作者：Nader Ghaffari Khaligh、Taraneh Mihankhah、Mohd Rafie Johan

  DOI：10.1016/j.molliq.2019.01.024

  日期：2019.3

  solubility in some common solvents. The catalytic activity of new SAIL was demonstrated for the one-pot mechanosynthesis of pyrano[4,3-b]pyrans, dihydropyrano[3,2-c]chromene and tetrahydrobenzo[b]pyrans using planetary ball mill under solvent-free conditions. This current mechanosynthesis methodology for the synthesis of 4H-pyran-annulated heterocyclic scaffolds displays a combination of the synthetic virtues

  在本研究中，一种新的低粘度磺酸官能化离子液体（SAIL）即。合成了4,4'-三亚甲基-N，N'-磺酸-二哌啶鎓氯化物，并用FTIR，1D和2D NMR以及质谱进行了表征。然后，确定了新的SAIL的一些特性，包括pH，粘度，密度和在某些常用溶剂中的溶解度。在无溶剂条件下，使用行星式球磨机证明了新SAIL对吡喃并[4,3- b ]吡喃，二氢吡喃并[3,2- c ]色烯和四氢苯并[ b ]吡喃的一锅机械合成具有催化活性。目前用于合成4 H的机械合成方法-吡喃环化的杂环支架结合了常规多组分反应的合成优点，生态效益和简单的机械催化方法的便利性。新的SAIL易于回收利用，可以重复使用多次，而不会造成严重的活动损失。
• 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。
• Ni(II)-Schiff base/SBA-15: a nanostructure and reusable catalyst for one-pot three-component green synthesis of 3,4-dihydropyrano[3,2-c]chromene derivatives
  作者：Nader Noroozi Pesyan、Ghasem Rezanejade Bardajee、Elmira Kashani、Marzieh Mohammadi、Hana Batmani

  DOI：10.1007/s11164-019-03954-6

  日期：2020.1

  base/SBA-15-catalyzed one-pot three-component cyclocondensation process was described via the reaction between malononitrile, 4-hydroxycoumarin, and various aldehydes in aqueous media for the synthesis of 3,4-dihydropyrano[3,2- c ]chromene derivatives. This nanocatalyst was characterized using FT-IR, SEM, TGA, TEM, BET, AFM, and XRD techniques. It is possible to reuse the heterogeneous catalyst without any marked

  通过丙二腈，4-羟基香豆素和各种醛在水性介质中的反应，描述了一种高效，快速且环境友好的Ni（II）-席夫碱/ SBA-15催化的单锅三组分环缩合工艺3，4-二氢吡喃并[3，2- c ]亚甲基 衍生物。使用FT-IR，SEM，TGA，TEM，BET，AFM和XRD技术对这种纳米催化剂进行了表征。可以重复使用多相催化剂而其催化活性没有任何显着变化至少五倍。该方法的其他显着特点包括纯净形式收率高，操作简便，操作温和得多，反应时间短，后处理简单并避免了危险试剂/溶剂的使用。