- Method for synthesizing coumarin-3-carboxylic acid compounds by one-pot two-step method
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The invention relates to a method for synthesizing coumarin-3-carboxylic acid compounds by a one-pot two-step method. The structural formula of the coumarin-3-carboxylic acid compounds is shown in the description, wherein R1 is H , Cl , Br, NO2 , CH3 and HO . According to the synthesis process of the coumarin-3-carboxylic acid compounds, malonic acid, acetone and substituted salicylaldehyde serve as raw materials, iodine serves as a catalyst, acetic anhydride serves as a solvent, a series of coumarin-3-carboxylic acid compounds are synthesized through a one-pot cascade reaction, and the efficiency and the yield are greatly improved compared with a fractional step method.
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Paragraph 0053; 0056; 0058; 0076; 0079; 0084-0090
(2021/06/12)
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- Green synthesis method of coumarin-3-carboxylic acid compound
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The invention relates to a green synthesis method of a coumarin-3-carboxylic acid compound. The synthesis process of the coumarin-3-carboxylic acid compound is as follows: R1 is H, Cl, Br, NO2, CH3 and HO. A series of coumarin-3-carboxylic acid compounds are synthesized in one step without a catalyst by taking R1-substituted salicylaldehyde and Meldrum's acid as raw materials and water as a reaction medium, the process steps are simple, the method has universality, reaction liquid can be repeatedly added for reaction, no waste or waste liquid is generated, the yield of a target product is greater than 54.3%, and the method is an environment-friendly green synthesis method.
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Paragraph 0053-0061; 0076
(2021/06/26)
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- Design, Synthesis, and Molecular Modeling Studies of Novel Coumarin Carboxamide Derivatives as eEF-2K Inhibitors
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Eukaryotic elongation factor-2 kinase (eEF-2K) is an unusual alpha kinase commonly upregulated in various human cancers, including breast, pancreatic, lung, and brain tumors. We have demonstrated that eEF-2K is relevant to poor prognosis and shorter patie
- Comert Onder, Ferah,Durdagi, Serdar,Sahin, Kader,Ozpolat, Bulent,Ay, Mehmet
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p. 1766 - 1778
(2020/03/04)
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- A Simple One-Pot Synthesis of Fully Substituted 1H-Pyridone[1,2-a]-Fused-1,3-Diazaheterocycles
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An efficient procedure for the synthesis of 7-(aryl)-8-nitro-2,3,6,7-tetrahydroimidazo[1,2-a]pyridinones, 8-(aryl)-9-nitro-3,4,7,8-tetrahydropyridone[1,2-a]pyrimidines and 9-(aryl)-10-nitro-2,3,4,5,8,9-hexahydropyridone[1,2-a]diazepine via one-pot three component reaction of diamine, nitroketene dithioacetal (1,1-bis(methylsulfanyl)-2-nitroethene), and coumarine-3- carboxylic acid derivatives in EtOH under reflux conditions is reported. The advantages of this procedure are simplicity, easy purification, good yields, and catalyst-free conditions. All products were confirmed by 1H- and 13C-NMR, IR, MS, and X-ray crystal structure analyses.
- Bayat, Mohammad,Rezaee, Monireh,Zhu, Long-Guan
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p. 2748 - 2754
(2017/09/26)
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- Synthesis and characterization of two novel biological-based nano organo solid acids with urea moiety and their catalytic applications in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives under mild and green conditions
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2-Carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid as novel, mild and biological-based nano organocatalysts with urea moiety were designed, synthesized and fully characterized by FT-IR, 1H NMR, 13C NMR, mass spectrometry, elemental analysis, thermal gravimetric, derivative thermal gravimetric, X-ray diffraction patterns, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, atomic force microscopy and UV/Vis analysis. The catalytic applications of 2-carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid were studied in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives via the condensation reaction between several aromatic aldehydes and 1-phenyl-3-methylpyrazol-5-one (synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols)), the Knoevenagel condensation of Meldrum's acid with salicylaldehyde derivatives (synthesis of coumarin-3-carboxylic acids) and the condensation of Meldrum's acid with aromatic aldehydes (synthesis of cinnamic acids) under mild and solvent-free conditions. In the presented studies, some products were formed and reported for the first time. The described nano organo solid acids have potential in industry.
- Zolfigol, Mohammad Ali,Ayazi-Nasrabadi, Roya,Baghery, Saeed
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p. 71942 - 71954
(2015/09/08)
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- Coumarin-Fused Coumarin: Antioxidant Story from N, N -Dimethylamino and Hydroxyl Groups
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Two coumarin skeletons can form chromeno[3,4-c]chromene-6,7-dione by sharing with the C=C in lactone. The aim of the present work was to explore the antioxidant effectiveness of the coumarin-fused coumarin via six synthetic compounds containing hydroxyl and N,N-dimethylamino as the functional groups. The abilities to quench 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+?), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical revealed that the rate constant for scavenging radicals was related to the amount of hydroxyl group in the scaffold of coumarin-fused coumarin. But coumarin-fused coumarin was able to inhibit DNA oxidations caused by ?OH, Cu2+/glutathione (GSH), and 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH) even in the absence of hydroxyl group. In particular, a hydroxyl and an N,N-dimethylamino group locating at different benzene rings increased the inhibitory effect of coumarin-fused coumarin on AAPH-induced oxidation of DNA about 3 times higher than a single hydroxyl group, whereas N,N-dimethylamino-substituted coumarin-fused coumarin possessed high activity toward ?OH-induced oxidation of DNA without the hydroxyl group contained. Therefore, the hydroxyl group together with N,N-dimethylamino group may be a novel combination for the design of coumarin-fused heterocyclic antioxidants.
- Xi, Gao-Lei,Liu, Zai-Qun
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p. 3516 - 3523
(2015/04/14)
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- Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors
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Abstract Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study.
- Asadipour, Ali,Alipour, Masoumeh,Jafari, Mona,Khoobi, Mehdi,Emami, Saeed,Nadri, Hamid,Sakhteman, Amirhossein,Moradi, Alireza,Sheibani, Vahid,Homayouni Moghadam, Farshad,Shafiee, Abbas,Foroumadi, Alireza
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supporting information
p. 623 - 630
(2013/12/04)
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- Triton-B adsorbed on flysh: An efficient support for the base catalysed reactions under microwave irradiations
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The application of Triton-B adsorbed on flyash (a waste material of thermal plants ) has been reported for the variety of base catalysed reactions such as synthesis of cinnamic acids by Deobner reaction, synthesis of 1-(2-hydroxyphenyl)-5-phenylpent-4-ene-1, 3-diones by Baker-Venkataraman reaction and synthesis of 3-carboxycoumarins by knoevenagel reaction. This material also acts as a support for the reaction and avoids the use of any solvent in the reaction maintaining the norms of Green Chemistry.
- Goel, Vijender
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p. 1725 - 1728
(2013/06/27)
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- Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives
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Several 3-carbonyl (1-26), 3-acyl (27-52), and 3-carboxyhydrazido (53-58) coumarins have been synthesized in high yields (72-99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.
- Secci, Daniela,Carradori, Simone,Bolasco, Adriana,Chimenti, Paola,Yá?ez, Matilde,Ortuso, Francesco,Alcaro, Stefano
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experimental part
p. 4846 - 4852
(2011/11/13)
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- Synthesis, selective anti-Helicobacter pylori activity, and cytotoxicity of novel N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides
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N-substituted-3-carboxamido-coumarin derivatives were prepared and evaluated for selective antibacterial activity against 20 isolates of Helicobacter pylori clinical strains, including five metronidazole resistant ones. Some of them possessed the best activity against H. pylori metronidazole resistant strains with MIC values lower than the drug reference (metronidazole). Furthermore, anti-inflammatory activity through the inhibition of the IL-8 production was investigated.
- Chimenti, Franco,Bizzarri, Bruna,Bolasco, Adriana,Secci, Daniela,Chimenti, Paola,Granese, Arianna,Carradori, Simone,Rivanera, Daniela,Zicari, Alessandra,Scaltrito, M. Maddalena,Sisto, Francesca
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experimental part
p. 4922 - 4926
(2010/10/02)
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- One-Pot Synthesis of 3-Carboxycoumarins via Consecutive Knoevenagel and Pinner Reactions in Water
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Chloro-, hydroxy-, methoxy-, and tert-butyl-substituted 3-carboxycoumarins have been prepared by one-pot procedure by reaction of suitably substituted salicylaldehydes with malononitrile in water. The over-all yields are high and the protocol does not require organic solvents.
- Fringuelli, Francesco,Piermatti, Oriana,Pizzo, Ferdinando
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p. 2331 - 2334
(2007/10/03)
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