Design and synthesis of coumarin-3-acylamino derivatives to scavenge radicals and to protect DNA

Yang, Yang; Liu, Qing‐Wen; Shi, Ye; Song, Zhanqian; Liu, Zai‐Qun

doi:10.1016/j.ejmech.2014.07.009

Cited by 23 publications

(9 citation statements)

References 39 publications

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“…The syntheses of the target compounds e1 – e20 are depicted in Scheme 1 . 3-Coumarin carboxylic acid ( c ) was synthesized from salicylaldehyde ( a ) according to literature procedures 38 and it was converted to the acyl chloride by using SOCl 2 . To obtain thiourea-substituted coumaryl-carboxamid derivatives ( e1 – e20 ), 2-oxo-2H-chromene-3-carbonyl chloride ( d ) was reacted with KSCN and various amines in CH 3 CN, respectively.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, biological activity and multiscale molecular modeling studies for coumaryl-carboxamide derivatives as selective carbonic anhydrase IX inhibitors

Kurt

Sönmez

Durdağı

et al. 2017

Journal of Enzyme Inhibition and Medicinal Chemistry

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New coumaryl-carboxamide derivatives with the thiourea moiety as a linker between the alkyl chains and/or the heterocycle nucleus were synthesized and their inhibitory activity against the human carbonic anhydrase (hCA) isoforms hCA I, II, VII and IX were evaluated. While the hCA I, II and VII isoforms were not inhibited by the investigated compounds, the tumour-associated isoform hCA IX was inhibited in the high nanomolar range. 2-Oxo-N-((2-(pyrrolidin-1-yl)ethyl)carbamothioyl)-2H-chromene-3-carboxamide (e11) exhibited a selective inhibitory action against hCA IX with the Ki of 107.9 nM. In order to better understand the inhibitory profiles of studied molecules, multiscale molecular modeling approaches were used. Different molecular docking algorithms were used to investigate binding poses and predicted binding energies of studied compounds at the active sites of the CA I, II, VII and IX isoforms.

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Section: Resultsmentioning

confidence: 99%

“…Spectral data of this compound were matched with the literature, white solid, 91% yield; mp. 145–147 °C 38 .…”

Section: Methodsmentioning

confidence: 99%

Synthesis, biological activity and multiscale molecular modeling studies for coumaryl-carboxamide derivatives as selective carbonic anhydrase IX inhibitors

Kurt

Sönmez

Durdağı

et al. 2017

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…[29] 7-tert-Butyl-6-hydroxy-4-methylcoumarin (5). 13 Hydroxy-4-methyl-6,8-bis(exo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl) (15…”

Section: -Tert-butyl-7-hydroxy-4-methylcoumarinmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Coumarins withtert‐Butyl and Terpene Substituents

Попова

Шевченко

Chukicheva

et al. 2019

Chemistry & Biodiversity

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Coumarins with terpene and tert‐butyl substituents were synthesized via Pechmann condensation reaction. New derivatives were investigated in different model system for the exhibition of antioxidant, radical scavenging and membrane‐protective activities. It has been found that 4‐methylcoumarin derivatives with monoterpene moieties exhibit high antioxidant activities. The most active and promising for further investigations is 5‐hydroxy‐6,8‐diisobornyl‐4‐methylcoumarin, containing two isobornyl substituents on the benzopyran ring.

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“…They are also key components of flavoring agent for a diverse set of food, such as soft drinks, yogurt, muffins etc. [25]. In particular, umbelliferone (1) , esculetin (2) , scopoletin (3) and quercetin (4) were found as potent antioxidant agents (Fig.…”

Section: Introductionmentioning

confidence: 95%

Microwave assisted synthesis of coumarin-purine derivatives: An approach to in vitro anti-oxidant, DNA cleavage, crystal structure, DFT studies and Hirshfeld surface analysis

Mangasuli

Hosamani

Managutti

2019

Heliyon

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An easy and efficient microwave-assisted protocol has been developed for the synthesis of coumarin-purine hybrids (3a-3j). The newly constructed 1,3-dimethyl-7-((substituted)-2-oxo-2H-chromen-4-yl)methyl)-1H-purine-2,6(3H,7H)-dione derivatives were evaluated for their in vitro antioxidant activity by DPPH free radical-scavenging ability assay and DNA cleavage by using calf thymus. The compound 3i, shows the most excellent DPPH scavenging activity with a –OH substitution at C7 of coumarin ring. In addition, the structure of compound 3f, has been elucidated using single crystal X-ray diffraction technique. Theoretical calculations (DFT) were carried out using Gaussian09 program package and B3LYP correlation function. Full geometry optimization were carried out using 6-311G++(d, p) basis set and the frontier orbital energy were presented. Hirshfeld surface analysis was used for the intermolecular interactions in the crystal structure. The experimental result of the compound 3f has been compared with the theoretical results and it was found that the experimental data are in a good agreement with the calculated values.

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Design and synthesis of coumarin-3-acylamino derivatives to scavenge radicals and to protect DNA

Cited by 23 publications

References 39 publications

Synthesis, biological activity and multiscale molecular modeling studies for coumaryl-carboxamide derivatives as selective carbonic anhydrase IX inhibitors

Synthesis, biological activity and multiscale molecular modeling studies for coumaryl-carboxamide derivatives as selective carbonic anhydrase IX inhibitors

Synthesis and Biological Evaluation of Novel Coumarins withtert‐Butyl and Terpene Substituents

Microwave assisted synthesis of coumarin-purine derivatives: An approach to in vitro anti-oxidant, DNA cleavage, crystal structure, DFT studies and Hirshfeld surface analysis

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