Abstract
A series of chalcone analogues and some of their derivatives were synthesized and subjected to the mosquito larvicidal study. Chalcones having electron releasing group(s) on either ring A or ring B showed high toxicity. Electron withdrawing group(s), especially at ring B, reduced the activity of chalcones. The activity was abruptly decreased due to replacement of ring A by CH3, extension of conjugation or blocking of α,β-unsaturated ketone part of chalcones by derivatization. Quantitative structure–activity relationship (QSAR) studies of these compounds were performed using various spatial, electronic and physicochemical parameters. Genetic Function approximation with linear and spline options was used as the chemometric tool for developing the QSAR models.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Abbott WS (1925) A method of computing the effectiveness of an insecticide. J Econ Entomol 18:265–267
Agarwala PK (ed) (1989) Carbon-13 NMR of flavonoids. Elsevier Science Publishers BV, The Netherlands, p 365
Boeck P, Falcão CAB, Leal PC, Yunes RA, Filho VC, Torres-Santos EC, Rogssi-Bergmann B (2006) Synthesis of chalcone analogues with increased antileishmanial activity. Bioorg Med Chem 14:1538–1545
Chang HT, Cheng SS, Chang ST, Su YC, Tsai KH, Chen WJ (2003) Mosquitocidal activity of leaf essential oil and its components from Calocedrus formosana. Q J Chen For 36:73–79
Cheng SS, Liu JY, Tsai KH, Chen WJ, Chang ST (2004) Chemical composition and mosquito larvicidal activity of essential oils from leaves of different Cinnamonium osmophloeum provenances. J Agric Food Chem 52:4395–4400
Das BP, Begum NA, Choudhury DN, Banerji J (2005) Larvicidal studies of chalcones and their derivatives. J Indian Chem Soc 82:161–164
Ducki S, Forrest R, Hadfield JA, Kendall A, Lawrence NJ, Mcgown AT, Rennison D (1998) Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg Med Chem Lett 8:1051–1056
Finney DJ (1971) Probit Analysis, 3rd edn. Cambridge University Press, London, UK
Frear DEH (1955) Chemistry of pesticides, 3rd edn. D van Norstrand Co, New York
Furniss BS, Hannaford AJ, Rogers V, Smith PWG, Tatchell AR (1984) Vogel’s textbook of practical organic chemistry, 9th edn. ELBS/Longman, London
Go ML, Liu M, Wilairat P, Rosenthal PJ, Saliba KJ, Kirk K (2004) Antiplasmodial chalcones inhibit sorbitol induced hemolysis of Plasmodium falciparum infected erythrocytes. Antimicrob Agents Chemother 44:3241–3245
Herencia F, Ferrandiz ML, Ubeda A, Dominguez JN, Charris JE, Lobo GM, Alcaraz MJ (1998) Synthesis and anti-inflammatory activity of chalcone derivatives. Bioorg Med Chem Lett 8: 1169–1174. http://www.accelrys.com/
Kumar P, Clark M (eds) (2005) Clinical medicine, 6th edn. Elsevier Saunders, UK, p 106
Liu M, Wilairat P, Go ML (2001) Antimalarial alkoxylated and hydroxylated chalcone: structure–activity relationship analysis. J Med Chem 44:3352–4443
Pollock JRA, Stevens R (eds) (1965) Dictionary of the organic compounds, 4th edn. Eyre and Spottishwood (Pubs.) Ltd, London
Rahuman AA, Gopalakrishnan G, Venkatesan P, Geetha K (2008) isolation and identification of mosquito larvicidal compound from Abutilon indicum (Linn.) Sweet. Parasitol Res 102:981–988
Rogers D, Hopfinger AJ (1994) Application of genetic function approximation to quantitative structure activity relationships and quantitative structure property relationships. J Chem Inf Comput Sci 34:854–866
Toda F, Tanaka K, Hamai K (1990) Aldol condensations in the absence of solvent: acceleration of the reaction and enhancement of the stereoselectivity. J Chem Soc Perkin Trans 1:3207–3209
van de Waterbeemd H (1995a) Advanced computer-assisted techniques in drug discovery. In: Mannhold R, Krogsgaard-Larsen P, Timmerman H (eds) Methods and principles in medicinal chemistry, vol 2. VCH, Weinheim
van de Waterbeemd H (1995b) Chemometric methods in molecular design. In: Mannhold R, Krogsgaard-Larsen P, Timmerman H (eds) Methods and principles in medicinal chemistry, vol 2. VCH, Weinheim
Yang YC, Lee SG, Lee HK, Kim MK, Lee SH, Lee HS (2002) A piperidine amide extracted from Piper Longum L. fruit shows activity against Ades aegypti mosquito larvae. J Agric Food Chem 50:3765–3767
Acknowledgements
The authors are thankful to the University Grants Commission, India for the financial support (UGC M.R.P. Grant No. 33-290/2007 (SR) to N.A.B.). Thanks are also due to DST-FIST and UGC-SAP programmes of Department of Chemistry, Siksha Bhavana, Visva Bharati University, Santiniketan, WB, India. We would also like to thank Dr. G.K. Das, Reader, Department of Chemistry, Siksha Bhavana, Visva Bharati University, Santiniketan, WB, India for his help in statistical analysis. The authors gratefully acknowledge the help provided by Prof. A. T. Khan, IIT-Guwahati, Assam, India in recording the 1H NMR spectra.
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Begum, N.A., Roy, N., Laskar, R.A. et al. Mosquito larvicidal studies of some chalcone analogues and their derived products: structure–activity relationship analysis. Med Chem Res 20, 184–191 (2011). https://doi.org/10.1007/s00044-010-9305-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-010-9305-6