2-amino-4-(3,4-methylenedioxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c][1]benzopyran-3-carbonitrile

• 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-methylenedioxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c][1]benzopyran-3-carbonitrile
• 英文别名: 2-amino-4-(benzo[d][1,3]dioxol-5-yl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3 carbonitrile；2-amino-4-(3,4-methylenedioxyphenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile；2-amino-4-(1,3-benzodioxol-5-yl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile；2-amino-4-(1,3-benzodioxol-5-yl)-5-oxo-4H-pyrano[3,2-c]chromene-3-carbonitrile
• 化学式: C₂₀H₁₂N₂O₅
• 分子量: 360.326
• InChiKey: ICSHLBYAACDPEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  环己酮 、 2-amino-4-(3,4-methylenedioxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c][1]benzopyran-3-carbonitrile 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以94%的产率得到8-amino-7-(benzo[d][1,3]dioxol-5-yl)-9,10,11,12-tetrahydrochromeno[3',4':5,6]pyrano[2,3-b]quinolin-6(7H)-one
  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
• 作为产物：
  描述：

  1,3-二氢-2-苯并呋喃-5-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-4-(3,4-methylenedioxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c][1]benzopyran-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

• 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。
• 离子液体促进的一锅法合成4H-吡喃并香豆素衍生物的方法
  申请人：河南师范大学

  公开号：CN110156809A

  公开（公告）日：2019-08-23

  本发明公开了一种离子液体促进的一锅法合成4H‑吡喃并香豆素衍生物的方法，以4‑羟基香豆素、芳香醛类化合物和丙二腈为反应底物，以功能化离子液体为催化剂，于室温搅拌反应0.5‑12h制得目标产物4H‑吡喃并香豆素衍生物。本发明所用离子液体催化剂制备简便，且原料具有良好的生物相容性，价廉易得；一锅法制备4H‑吡喃并香豆素衍生物的方法反应条件温和，无需添加溶剂等助剂，原子经济性高；该反应体系对设备无腐蚀性，对反应器无特殊要求；此催化体系的操作及后处理过程简单；离子液体催化剂可以方便的回收使用。因此该方法是工业化合成4H‑吡喃并香豆素衍生物的首选方法。
• Synthesis of 2-Amino-4-Aryl-5-Oxo-4,5-Dihydropyrano[3,2-<i>c</i>] Chromene Derivatives Catalysed by KF-Montmorillonite
  作者：Da-Qing Shi、Nan Wu、Qi-Ya Zhuang

  DOI：10.3184/030823408x347585

  日期：2008.9

  A series of 2-amino-4-aryl-5-oxo-4,5-dihydropyrano[3,2- c]chromene derivatives has been synthesised by the reaction of 4-hydroxycoumarin and substituted cinnamonitriles catalysed by KF-montmorillonite. The structures were characterised by IR and ¹H NMR spectroscopic data and confirmed by X-ray diffraction analysis.

  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。
• Convenient Preparation of Pyrano Benzopyranes in Aqueous Media
  作者：M. Kidwai、S. Saxena

  DOI：10.1080/00397910600764774

  日期：2006.9

  The three-component reaction of aldehyde, malononitrile, and 4-hydroxy coumarin has been efficiently performed in aqueous K2CO3 using a simple, clean, environmentally benign, novel procedure employing microwave irradiation. The observed yields and enhancement in reaction rates can be attributed to the uniform heating effect of microwave. The microwave-accelerated reaction technique not only eliminates the use of external base and organic solvents but also requires only water in both the reaction step and workup, thus rendering the whole procedure into a truly ecofriendly protocol.
• Wang, Jing; Shi, Daqing; Zhuang, Qiya, Journal of Chemical Research, 2004, # 12, p. 818 - 820
  作者：Wang, Jing、Shi, Daqing、Zhuang, Qiya、Wang, Xiangshan、Hu, Hongwen

  DOI：——

  日期：——