1887
  1. الرئيسية
  2. A-Z Publications
  3. QScience Connect
  4. المجلد 2014, العدد 1
  5. المقالة
Volume 2014, Issue 1
  • E-ISSN: 2223-506X

ملخص

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.
Loading

جارٍ تحميل قياسات المقالة...

/content/journals/10.5339/connect.2014.18
٢٠١٤-٠٩-٠١
٢٠٢٤-١٢-٢١
Loading full text...

Full text loading...

/deliver/fulltext/connect/2014/1/connect.2014.18.html?itemId=/content/journals/10.5339/connect.2014.18&mimeType=html&fmt=ahah

References

  1. Breslow R, Marita U, Rideout DC. Selective diels-alder reactions in aqueous solutions and suspensions. Tetrahedron Lett. 1983; 24::1901–1904.
     [Google الباحث العلمي]
  2. Breslow R, Marita U. On the origin of product selectivity in aqueous diels-alder reactions. Tetrahedron Lett. 1984; 25::1239–1240.
     [Google الباحث العلمي]
  3. Otto S, Bertoncin F, Engberts JBFN. Lewis acid catalysis of a diels-alder reaction in water. J Am Chem Soc. 1996; 118::7702–7707.
     [Google الباحث العلمي]
  4. Otto S, Engberts JBFN. A systematic study of ligand effects on a Lewis-acid-catalyzed diels-alder reaction in water. Water-enhanced enantioselectivity. J Am Chem Soc. 1999; 121::6798–6806.
     [Google الباحث العلمي]
  5. Fringuelli F, Piermatti O, Pizzo F, Vaccaro L. Recent advances in Lewis acid catalyzed diels-alder reactions in aqueous media. Eur J Org Chem. 2001; 2001::439–455.
     [Google الباحث العلمي]
  6. Mubofu EB, Engberts JBFN. Specific acid catalysis and Lewis acid catalysis of diels-alder reactions in aqueous media. J Phys Org Chem. 2004; 17::180–186.
     [Google الباحث العلمي]
  7. Boersma AJ, Feringa BL, Roelfes G. α,β-Unsaturated 2-acyl imidazoles as a practical class of dienophiles for the DNA-based catalytic asymmetric diels-alder reaction in water. Organic Lett. 2007; 9::3647–3650.
     [Google الباحث العلمي]
  8. Boersma AJ, de Bruin B, Feringa BL, Roelfes G. Ligand denticity controls enantiomeric preference in DNA-based asymmetric catalysis. Chem Commun. 2012; 48::2394–2396.
     [Google الباحث العلمي]
  9. Rideout DC, Breslow R. Hydrophobic acceleration of diels-alder reactions. J Am Chem Soc. 1980; 102::7816–7817.
     [Google الباحث العلمي]
  10. Otto S, Engberts JBFN. Lewis acid catalysis of a diels-alder reaction in water. Tetrahedron Lett. 1995; 36::2645–2648.
     [Google الباحث العلمي]
  11. Megens RP, Roefes G. Asymmetric catalysis with helical polymers. Chemistry. 2011; 17::8514–8523.
     [Google الباحث العلمي]
  12. Jin Q, Zhang L, Cao H, Wang T, Zhu X, Jiang J, Liu M. Self-assembly of copper(II) ion-mediated nanotube and its supramolecular chiral catalytic behavior. Langmuir. 2011; 27::13847–13853.
     [Google الباحث العلمي]
  13. Roelfes G, Boersma AJ, Feringa BL. Highly enantioselective DNA-based catalysis. Chem Commun. 2006;635–637.
     [Google الباحث العلمي]
  14. Kuo CH, Niemeyer CM, Fruk L. Bimetallic copper-heme-protein-DNA hybrid catalyst for diels-alder reaction. Croat Chem Acta. 2011; 84::269–275.
     [Google الباحث العلمي]
  15. Oltra NS, Roelfes G. Modular assembly of novel DNA-based catalysts. Chem Commun. 2008;6039–6041.
     [Google الباحث العلمي]
  16. Otto S, Engberts JBFN, Kwak JCT. Million-fold acceleration of a diels-alder reaction due to combined Lewis acid and Micellar catalysis in water. J Am Chem Soc. 1998; 120::9517–9525.
     [Google الباحث العلمي]
  17. Thirunarayanan G, Vanangamudi G, Sathiyendiran V, Ravi K. Solvent-free synthesis, spectral studies and antioxidant activities of some 6-substitued (-bromo-2-naphthyl ketones and their esters. Indian Journal of Chemistry. 2011; 50B::593–604.
     [Google الباحث العلمي]
  18. Thirunarayanan G, Vanangamudi G. Synthesis, spectral studies, antimicrobial, antioxidant and insect antifeedant activities of some 9H-fluorene-2-yl-keto-oxiranes. Spectrochim Acta A Mol Biomol Spectrosc. 2011; 81::390–396.
     [Google الباحث العلمي]
  19. Thirunarayanan G, Vanangamudi G, Subramanian M. Solvent-free synthesis, spectral linearity, antimicrobial, antioxidant and insect antifeedant activities of some 1-methyl-2-pyrrolyl chalcones. Org Chem Indian J. 2013; 9::1–16.
     [Google الباحث العلمي]
  20. Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J. New environmentally-friendly solvent-free synthesis of imines using calcium oxide under microwave irradiation. Res Chem Intermed. 2007; 33::541–545.
     [Google الباحث العلمي]
  21. el-Mogazi D, Lisk DJ, Weinstein LK. A review of physical, chemical and biological properties of fly ash and effects on agricultural ecosystems. Sci Total Environ. 1988; 74::1–37.
     [Google الباحث العلمي]
  22. Bauer AW, Kirby WMM, Sherris JC, Truck M. Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol. 1966; 45::493–496.
     [Google الباحث العلمي]
  23. Vanangamudi G, Subramanian M, Thirunarayanan G. Synthesis, spectral linearity, antimicrobial, antioxidant and insect antifeedant activities of some 2,5-dimethyl-3-thienyl chalcones. Arabian J Chem. 2013.
     [Google الباحث العلمي]
  24. Dethler's VG. Chemical Insect Attractants and Repellents, Blackistan, Philadelphia. 1947;210.
     [Google الباحث العلمي]
  25. Thirunarayanan G, Mayavel P, Thirumurthy K. Fly-ash:H2SO4 catalyzed solvent-free efficient synthesis of some aryl chalcones under microwave irradiation. Spectrochim Acta A Mol Biomol Spectrosc. 2012; 91::18–22.
     [Google الباحث العلمي]
  26. a) Surendra Reddy B, Babul Reddy A, Ramachandra Reddy G, Raveendra Reddy P. Synthesis and antibacterial activity of novel [3-(4-substitutedphenylamino)-8-azabicyclo[3.2.1]oct-8yl]phenylmethanone derivatives. J Korean Chem Soc. 2011;55:969–73; b) Biswal S, Sahoo U, Sethy S, Kumar HKS, Banerjee M. Indole: the molecule of diverse biological activities. Asian J Pharm Clin Res. 2012;5:1–6; c) Vanangamudi G, Ranganathan K, Thirunarayanan G. Synthesis, spectral and biological activities of some substituted styryl 2-phenothiazinyl ketones. World J Chem. 2012;7:22–33.
  27. Thirunarayanan G. Insect antifeedant potent chalcones. J Indian Chem Soc. 2008; 85::447–451.
     [Google الباحث العلمي]
  28. Kanchana DV, Kasaikina TO. Bio-antioxidants-A chemical base of their antioxidant activity and beneficial effect on human health. Curr Med Chem. 2013; 20:7:4784–4805.
     [Google الباحث العلمي]
  29. Narsinghani T, Sharma MC, Bhargav S. Synthesis, docking studies and antioxidant activity of some chalcone and aurone derivatives. Med Chem Res. 2013; 22:9:4059–4068.
     [Google الباحث العلمي]
  30. Babasaheb P, Bandgar LK, Shrikant VA, Lonikar HV, Chavan SN, Shringare SA, Patil SS, Jalde BA, Koti NA, Dhole RN, Gacche AS. Synthesis of novel carbazole chalcones as radical scavenger, antimicrobial and cancer chemopreventive agents. J Enzyme Inhib Med Chem. 2013; 28:3:593–600.
     [Google الباحث العلمي]
  31. Thirunarayanan G, Surya S, Srinivasan S, Vanangamudi G, Sathiyendiran V. Synthesis and insect antifeedant activities of some substituted styryl 3,4-dichlorophenyl ketones. Spectrochim Acta A Mol Biomol Spectrosc. 2010; 75::152–156.
     [Google الباحث العلمي]
  32. Thirunarayanan G. Fly-ash catalyzed Friedel-Crafts cinnamoylation reaction in solvent free conditions: synthesis of α,β-unsaturated ketones under microwave irradiation. Iup J Chem. 2010; 3::35–54.
     [Google الباحث العلمي]
/content/journals/10.5339/connect.2014.18
Loading
Synthesis, antimicrobial, antioxidant and insect antifeedant activities of some aryl bicyclo[2.2.1]heptene-2-yl-methanones
QScience Connect 2014, 18 (٢٠١٤); https://doi.org/10.5339/connect.2014.18
/content/journals/10.5339/connect.2014.18
/content/journals/10.5339/connect.2014.18
Loading

جارٍ تحميل البيانات والوسائط...

Supplements

Supplementary File 1

  • نوع المستند: Research Article
الموضوعات الرئيسية antimicrobial activities, antioxidant activity, bicyclo[2.2.1]heptene-2-yl-methanones, Diels-Alder reaction and insect antifeedant activity

الأكثر اقتباسًا لهذا الشهر Most Cited RSS feed

هذه الخانة مطلوبة
يُرجى إدخال عنوان بريد إلكتروني صالح
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error