Quantitative structure-activity relationships of mosquito larvicidal chalcone derivatives

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 2, 2012, Pages 692-697

  Pasquale, Gustavo ^a   Romanelli, Gustavo P ^a,b   Autino, Juan C ^a   García, Javier ^c   Ortiz, Erlinda V ^d   Duchowicz, Pablo R ^c  

^a UNIVERSIDAD NACIONAL DE LA PLATA   (Argentina)

^b DEPARTAMENTO DE QUÍMICA   (Argentina)

^c INSTITUTO DE INVESTIGACIONES FISICOQUÍMICAS TEÓRICAS Y APLICADAS INIFTA   (Argentina)

^d UNIVERSIDAD NACIONAL DE CATAMARCA   (Argentina)

Author keywords

chalcone derivatives; molecular descriptors; mosquito larvicidal activity; QSAR theory

Indexed keywords

ACTIVE COMPOUNDS; CARBONYL GROUPS; CHALCONE DERIVATIVES; CHALCONES; DERIVATIZATIONS; ELECTRON WITHDRAWING GROUP; ELECTRON-RICH; EXPERIMENTAL VALUES; LARVICIDAL ACTIVITIES; MOLECULAR DESCRIPTORS; QSAR MODEL; QSAR THEORY; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP STUDIES;

DYES; MOLECULAR GRAPHICS; ORGANIC CHEMICALS; TOXIC MATERIALS;

COMPUTATIONAL CHEMISTRY;

CHALCONE; DRUG DERIVATIVE; INSECTICIDE;

ANIMAL; ARTICLE; CHEMISTRY; DRUG EFFECT; LARVA; MOSQUITO; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANIMALS; CHALCONE; CULICIDAE; INSECTICIDES; LARVA; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84863418230     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf203374r     Document Type: Article

References (41)

1. Dimmock, J. R.; Elias, D. W.; Beazely, M. A.; Kandepu, N. M. Bioactivities of chalcones Curr. Org. Chem. 1999, 6, 1125-1149
2. Cave, G. W.; Raston, C. L. Toward benign syntheses of pyridines involving sequential solvent free aldol and Michael addition reactions Chem. Commun. 2000, 22, 2199-2200
3. Mitsutani, A. Future possibilities of recently commercialized acid/base-catalyzed chemical processes Catal. Today 2002, 73, 57-63 (Pubitemid 34449059)
4. Calloway, N. O.; Green, L. D. Reactions in the presence of metallic halides. α,β-Unsaturated ketone formation as a side reaction in Friedel-Crafts acylations J. Am. Chem. Soc. 1937, 59, 809-811
5. Sipos, G.; Sirokman, F. Chalcon formation of different substituted acetophenones and p-hydroxy-benzaldehyde Nature 1964, 202, 489
6. Le Gall, E.; Texier-Boullet, F.; Hamelien, J. ChemInform abstract: simple access to α,β-unsaturated ketones by acid-catalyzed solvent-free reactions Synth. Commun. 1999, 29, 3651-3657 (Pubitemid 29384307)
7. Narender, T.; Papi Reddy, K. A simple and highly efficient method for the synthesis of chalcones by using borontrifluoride-etherate Tetrahedron Lett. 2007, 48, 3177-3180 (Pubitemid 46527769)
8. Rao, Y. K.; Fang, S.-H.; Tzeng, Y.-M. Differential effects of synthesized 2′-oxygenated chalcone derivatives: modulation of human cell cycle phase distribution Bioorg. Med. Chem. 2004, 12, 2679-2686 (Pubitemid 38542792)
9. Chen, M.; Theander, T. G.; Christensen, S. B.; Hviid, L.; Zhai, L.; Kaharazmi, A. A new antimalarial agent, inhibits in vitro growth of the human malaria parasite Plasmodium falciparum and protects mice from P. yoelii infection Antimicrob. Agents Chemother. 1994, 38, 1470-1475 (Pubitemid 24203554)
10. Fang, N.; Casida, J. E. New bioactive flavonoids and stilbenes in cubé resin insecticide J. Nat. Prod. 1999, 62, 205-210 (Pubitemid 29137889)
11. Chen, M.; Zhai, L.; Christensen, S. B.; Theander, T. G.; Kharazmi, A. Inhibition of fumarate reductase in Leishmania major and L. donovani by chalcones Antimicrob. Agents Chemother. 2001, 45, 2023-2029 (Pubitemid 32591693)
12. Bandgar, B. P.; Patil, S. A.; Korbad, B. L.; Nile, S. H.; Khobragade, C. N. Synthesis and biological evaluation of β-chloro vinyl chalcones as inhibitors of TNF-α and IL-6 with antimicrobial activity Eur. J. Med. Chem. 2010, 45, 2629-2633
13. Hsieh, H. K.; Tsao, L. T.; Wang, J. P.; Lin, C. N. Synthesis and anti-inflammatory effect of chalcones J. Pharm. Pharmacol. 2000, 52, 163-171
14. Zhao, L.-M.; Jin, H.-S.; Sun, L.-P.; Piao, H.-R.; Quan, Z.-S. Synthesis and evaluation of antiplatelet activity of trihydroxychalcone derivatives Bioorg. Med. Chem. Lett. 2005, 15, 5027-5029 (Pubitemid 41400178)
15. Liu, M.; Wilairat, P.; Go, L. M. Antimalarial alkoxylated and hydroxylated chalcones: structure-activity relationship analysis J. Med. Chem. 2001, 44, 4443-4452 (Pubitemid 33131668)
16. Nielsen, S. F.; Chen, M.; Theander, T. G.; Kharazmi, A.; Christensen, S. B. Synthesis of antiparasitic licorice chalcones Bioorg. Med. Chem. Lett. 1995, 5, 449-452
17. Miranda, C. L.; Aponso, G. L.; Stevens, J. F.; Deinzer, M. L.; Buhler, D. R. Antioxidant and prooxidant actions of prenylated and nonprenylated chalcones and flavonoids in vitro J. Agric. Food Chem. 2000, 48, 3876-3884
18. Svetaz, L.; Tapia, A.; López, S. N.; Furlán, R. L. E.; Petenatti, E.; Pioli, R.; Schmeda-Hirschmann, G.; Zacchino, S. A. Antifungal chalcones and new caffeic acid esters from Zuccagnia punctata acting against soybean infecting fungi J. Agric. Food Chem. 2004, 52, 3297-3300
19. Thirunarayanan, G.; Vanangamudi, G. Insect antifeedant potent chalcones J. Indian Chem. Soc. 2008, 85, 447-451 (Pubitemid 351829315)
20. Jin, H.; Geng, Y.; Yu, Z.; Tao, K.; Hou, T. Lead optimization and anti-plant pathogenic fungi activities of daphneolone analogues from Stellera chamaejasme L Pest Biochem. Physiol. 2009, 93, 133-137
21. Tyrunarayanan, G.; Surya, S.; Srinivasan, S.; Vanangamudi, G.; Sathiyendiran, V. Synthesis and insect antifeedant activities of some substituted styryl 3,4-dichlorophenyl ketones Spectrochim. Acta Part A 2010, 75, 152-156
22. Hansch, C.; Leo, A. Exploring QSAR. Fundamentals and Applications in Chemistry and Biology; American Chemical Society: Washington, DC, 1995.
23. Hansch, C.; Fujita, T. Classical and three-dimensional QSAR in agrochemistry J. Am. Chem. Soc. 1995, 606, 318-329
24. Kubinyi, H. QSAR: Hansch Analysis and Related Approaches; Wiley-Interscience: New York, 2008.
25. Puzyn, T.; Leszczynski, J.; Cronin, M. T. Recent Advances in QSAR Studies: Methods and Applications, 1st ed.; Springer: New York, 2009.
26. Begum, N. A.; Roy, N.; Laskar, R. A.; Roy, K. Mosquito larvicidal studies of some chalcone analogues and their derived products: structure-activity relationship analysis Med. Chem. Res. 2011, 20, 184-191
27. Romanelli, G. P.; Pasquale, G.; Sathicq, A.; Thomas, H.; Autino, J. C.; Vázquez, P. Synthesis of chalcones catalyzed by aminopropylated silica sol-gel under solvent-free conditions J. Mol. Catal. A: Chem. 2011, 340, 24-32
28. Duchowicz, P. R.; Goodarzi, M.; Ocsachoque, M. A.; Romanelli, G. P.; Ortiz, E. V.; Autino, J. C.; Bennardi, D. O.; Ruiz, D.; Castro, E. A. QSAR analysis on Spodoptera litura antifeedant activities for flavone derivatives Sci. Total Environ. 2009, 408, 277-285
29. Goodarzi, M.; Duchowicz, P. R.; Wu, C. H.; Fernández, F. M.; Castro, E. A. New hybrid genetic based support vector regression as QSAR approach for analyzing flavonoids-GABA(A) complexes J. Chem. Inf. Model. 2009, 49, 1475-1485
30. Romanelli, G. P.; Virla, E. G.; Duchowicz, P. R.; Gaddi, A. L.; Ruiz, D. M.; Bennardi, D. O.; Ortiz, E. V.; Autino, J. C. Sustainable synthesis of flavonoid derivatives, QSAR study and insecticidal activity against the fall armyworm, Spodoptera frugiperda (Lep.: Noctuidae) J. Agric. Food Chem. 2010, 58, 6290-6295
31. Hyperchem 7 (Hypercube, Inc.), http://www.hyper.com (last accessed on Oct 31, 2011).
32. Dragon Milano Chemometrics and QSAR Research Group, http://michem.disat. unimib.it/chm (last accessed on Oct 31st, 2011).
33. Duchowicz, P. R.; Castro, E. A.; Fernández, F. M.; González, M. P. A new search algorithm of QSPR/QSAR theories: normal boiling points of some organic molecules Chem. Phys. Lett. 2005, 412, 376-380 (Pubitemid 41203394)
34. Duchowicz, P. R.; Castro, E. A.; Fernández, F. M. Alternative algorithm for the search of an optimal set of descriptors in QSAR-QSPR studies MATCH Commun. Math. Comput. Chem. 2006, 55, 179-192
35. Mercader, A. G.; Duchowicz, P. R.; Fernández, F. M.; Castro, E. A. QSPR study of solvent quenching of the 5D0→7F2 emission of Eu(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionate)3 Chem. Phys. Lett. 2008, 462, 352-357
36. Mercader, A. G.; Duchowicz, P. R.; Fernandez, F. M.; Castro, E. A. Replacement method and enhanced replacement method versus the genetic algorithm approach for the selection of molecular descriptors in QSPR/QSAR theories J. Chem. Inf. Model. 2010, 50, 1542-1548
37. Hawkins, D. M.; Basak, S. C.; Mills, D. Assessing model fit by cross validation J. Chem. Inf. Comput. Sci. 2003, 43, 579-586
38. Wold, S.; Eriksson, L. Statistical validation of QSAR results. In Chemometrics Methods in Molecular Design; van de Waterbeemd, H., Ed.; VCH: Weinheim, Germany, 1995; pp 309-318.
39. Draper, N. R.; Smith, H. Applied Regression Analysis; Wiley: New York, 1981.
40. Balaban, A. T.; Balaban, T. S. New vertex invariants and topological indices of chemical graphs. Based on information on distances J. Math. Chem. 1991, 8, 383-397
41. Burden, F. R. Molecular identification number for substructure searches J. Chem. Inf. Comput. Sci. 1989, 29, 225-227