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Volume 2014, Issue 1
  • EISSN: 2223-506X

Abstract

The aim of this study was to synthesize aryl heptene[2.2.1]methanone derivatives, including 2-naphthyl-based heptene[2.2.1]methanones, by an aqueous phase fly-ash catalyzed [4+2] cycloaddition Diels-Alder reaction of cyclopentadiene and aryl chalcones: to evaluate their antimicrobial, antioxidant and insect antifeedant activities. Green solvent ethanol-assisted aqueous phase fly-ash catalyzed [4+2] cycloaddition Diels-Alder reaction, was adopted for the synthesis of aryl heptene[2.2.1]methanone derivatives. These methanones were characterized by IR, NMR and mass spectroscopical data. The antimicrobial and antioxidant activities of the synthesized methanones were evaluated using and bacteria, fungal species, DPPH radical scavenging and 4th instar larvae castor leaf disc, bio-assay methods. Yields of the synthesized aryl heptene[2.2.1]methanone derivatives were over 60%. All compounds resulted in a 20–24 mm zone of inhibition for at least one bacterial strain. Methanones 13, 14, 16, 18 and 19 resulted in maximal antifungal activities against . and fungal species. Compound 17 shows significant anti- oxidant activity against DPPH radical scavenging activity. Ketone 13 resulted in maximal insect antifeedant activities of methanones (compounds 11–19). A series of methanone derivatives have been synthesized by aqueous-phase fly-ash-catalyzed Diels-Alder [4+2] cycloaddition of cyclopentadiene and aryl -chalcones. The parent, halogen and dimethylamino substituted compounds shown significant antibacterial activity against , and bacterial strains. Methanone that possesses dimethylamino, halogens, methoxy and nitro substituents shows significant antifungal activities against . and fungal strains. Antioxidant activities were measured; the compounds containing hydroxy and methoxy substituents showed antioxidant activity. Compound 13 shows insect antifeedant activity against the 4th instar larvae

© 2014 Thirunarayanan, licensee Bloomsbury Qatar Foundation Journals.
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2014-09-01
2024-11-07
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/content/journals/10.5339/connect.2014.18
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Synthesis, antimicrobial, antioxidant and insect antifeedant activities of some aryl bicyclo[2.2.1]heptene-2-yl-methanones
QScience Connect 2014, 18 (2014); https://doi.org/10.5339/connect.2014.18
/content/journals/10.5339/connect.2014.18
/content/journals/10.5339/connect.2014.18
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  • Article Type: Research Article
Keyword(s): antimicrobial activities, antioxidant activity, bicyclo[2.2.1]heptene-2-yl-methanones, Diels-Alder reaction and insect antifeedant activity

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