Utility of 3-Acetyl-6-bromo-2H-chromen-2-one for the Synthesis of New Heterocycles as Potential Antiproliferative Agents

Gomha, Sobhi M.; Zaki, Yasser H.; Abdelhamid, Abdou O.

doi:10.3390/molecules201219803

Cited by 56 publications

(34 citation statements)

References 33 publications

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“…Bis‐coumarin with C‐3 position analogue displayed potent activity against different microbes than its mono‐coumarin (Figure , C) . In addition, various 3‐substituted coumarins linked with imidazole, thiazole and thiadiazole has been reported as good anti‐microbials and as a new class of anti‐tumor agent against liver carcinoma recently. A long aliphatic chain of bis‐triazoles bridged with C‐5 and C‐7 coumarin moiety showed greater activity against bacterial and fungal strains and gave the best anti‐MRSA than mono‐triazole (Figure , D)…”

Section: Introductionmentioning

confidence: 99%

Click Chemistry Inspired Design, Synthesis and Molecular Docking Studies of Coumarin, Quinolinone Linked 1,2,3‐Triazoles as Promising Anti‐Microbial Agents

et al. 2018

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A series of new coumarin, quinolinone and benzyl linked 1,2,3‐triazole derivatives have been synthesized and screened for their anti‐bacterial and anti‐fungal activities. Results of bioassay indicate that, compounds containing chloro and methoxy substituents in coumarin (6 j), chloro substitution in quinolinone (7 g) and 3‐chloro benzyl analogue (8 f) exhibit excellent anti‐bacterial activities. The results of anti‐fungal activities also reveal that methoxy and chloro substituted coumarins (6 e and 6 j) were highly active against yeast strains. In addition, chloro and methyl substituted coumarins (6 h and 6 i) were also exhibited excellent activity. Further, methyl substituted quinolinone with chloro substituted coumarin (7 f) was found to highly active against yeast fungi and filamentous strain A.niger. It is evident from the results obtained and SAR studies that electron withdrawing or donating character of the substituents do not seem to be a major factor in increasing or decreasing anti‐microbial activity.

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Section: Introductionmentioning

confidence: 99%

Click Chemistry Inspired Design, Synthesis and Molecular Docking Studies of Coumarin, Quinolinone Linked 1,2,3‐Triazoles as Promising Anti‐Microbial Agents

et al. 2018

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“…In light of the above findings and in continuation of our efforts to synthesize new anticancer compounds [43][44][45][46][47][48][49][50][51][52], the aim of presented report is to synthesize a new series of pyrazolyl-pyridines via multicomponent reactions which are expected to be active as antitumor agents.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of Novel Pyrazole-Based Heterocycles as Potential Antitumor Agents

et al. 2017

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Abstract:A new series of pyrazolylpyridines was prepared by reaction of ethyl-3-acetyl-1,5-diphenyl-1H-pyrazole-4-carboxylate with the appropriate aldehyde, malononitrile, or ethyl acetoacetate and an excess of ammonium acetate under reflux in acetic acid. Similarly, two novel bipyridine derivatives were prepared by the above reaction using terephthaldehyde in lieu of benzaldehyde derivatives. In addition, a series of 1,2,4-triazolo[4,3-a]pyrimidines was synthesized by a reaction of 6-(pyrazol-3-yl)pyrimidine-2-thione with a number of hydrazonoyl chlorides in dioxane and in the presence of triethylamine. The structure of the produced compounds was established by elemental analyses and spectral methods, and the mechanisms of their formation was discussed. Furthermore, the pyrazolyl-pyridine derivatives were tested as anticancer agents and the results obtained showed that some of them revealed high activity against human hepatocellular carcinoma (HEPG2) cell lines.

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“…Due to the interesting activity of coumarins as biological agents, considerable attention has been focused on this class of heterocycles. The pharmaceutical importance of these compounds lies in the fact that they can be utilized as anti‐inflammatory , anticancer , anticoagulant , antimicrobial, and antioxidant activities . A literature survey revealed that a special attention was given to 1,3,4‐thiadiazole derivatives that proved to have promising biological activities such as antimicrobial , anticancer , antioxidant , antiamoebic , anticonvulsant , anti‐inflammatory, and analgesic activities .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Antimicrobial Activity of Some Novel Heterocyclic Compounds from 5‐Bromosalicylaldehyde

Abdel‐Aziem

Baaiu

Abdelhamid

2017

Journal of Heterocyclic Chem

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A novel series of coumarins, thiadiazoles, thiazoles, and pyridines were synthesized via reaction of 5‐bromosalicylaldehyde with different reagents. Thus, 5‐bromosalicylaldehyde 1 was reacted with compounds 2a–d affording iminocoumarins 3a–d, which on hydrolysis with 10% hydrochloric acid, afforded coumarins 4a–d, respectively. On the other hand, reaction of 1 with benzylhydrazinecarbodithioate 5 afforded derivative 6, which reacted with hydrazonoyl halides 7a–f, afforded 1,3,4‐thiadiazoles 11a–f, respectively. Moreover, thiazoles 15 and 16 were obtained via reaction of 1 with thiocarbohydrazide 13 and hydrazonoyl halides. However, condensation of 2‐acetyl‐5‐bromobenzofuran 17 with benzaldehyde afforded chalcone 18, which reacted with pyridiniumbromides 19a–c, afforded pyridines 20a–c, respectively. Furthermore, pyridines 21–24 were synthesized from the reaction of chalcone 18 with different active methylene compounds. Reaction of 24 with ethylchloroacetate, chloroacetone, and chloroacetonitrile afforded thienopyridines 26a–c, respectively. The structures of the newly synthesized compounds were established based on their spectral data and elemental analyses. Also, selected newly synthesized compounds were screened for their antimicrobial activity against various microorganisms by disk diffusion method.

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Utility of 3-Acetyl-6-bromo-2H-chromen-2-one for the Synthesis of New Heterocycles as Potential Antiproliferative Agents

Cited by 56 publications

References 33 publications

Click Chemistry Inspired Design, Synthesis and Molecular Docking Studies of Coumarin, Quinolinone Linked 1,2,3‐Triazoles as Promising Anti‐Microbial Agents

Click Chemistry Inspired Design, Synthesis and Molecular Docking Studies of Coumarin, Quinolinone Linked 1,2,3‐Triazoles as Promising Anti‐Microbial Agents

An Efficient Synthesis of Novel Pyrazole-Based Heterocycles as Potential Antitumor Agents

Synthesis and Evaluation of Antimicrobial Activity of Some Novel Heterocyclic Compounds from 5‐Bromosalicylaldehyde

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