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Synthesis and antimicrobial screening of some novel chalcones and flavanones substituted with higher alkyl chains

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Abstract

As a part of our program to generate some novel flavonoid frameworks substituted with higher alkyl groups as possible antimicrobial agents, we have in total synthesized twelve novel chalcones (1116) and their corresponding flavanones (1722) substituted with either nonyl or dodecyl chains in ring B in very good to excellent yields. The synthesized compounds have been screened for their antimicrobial potential against six bacterial and four fungal strains. The tested compounds, in general, showed significant antibacterial and comparable antifungal activities. While the chalcone (16) with a dodecyl chain showed highly promising antibacterial activity against almost all the organisms tested, the chalcone (13) with nonyl chain showed promising antifungal activity against Candida rugosa and Aspergillus niger strains.

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References

  • Blazevic N, Kolbah D, Belin B, Sunjic V, Kajfez F (1979) Hexamethylenetetramine, a versatile reagent in organic synthesis. Synthesis 3:161–176

    Article  Google Scholar 

  • Buer CS, Imin N, Djordjevic MA (2010) Flavonoids : new roles for old molecules. J Int Plant Biol 52:98–111

    Article  CAS  Google Scholar 

  • Cheng CY, Huges CA, Barnard KR, Larcombe K (2000) Manganese in copper solvent extraction and electrowinning. Hydrometallurgy 58:135–150

    Article  CAS  Google Scholar 

  • Clinical And Laboratory Standards Institute (2008) Performance Standards for Antimicrobial Susceptibility Tests. Eighteen informational supplement M100-S18

  • Cushnie TPT, Lamb AJ (2005) Antimicrobial activity of flavonoids. Int J Antimicrob Agents 26:343–346

    Article  CAS  PubMed  Google Scholar 

  • Cushnie TPT, Lamb AJ (2011) Recent advances in understanding the antibacterial properties of flavonoids. Int J Antimicrob Agents 38:99–107

    Article  CAS  PubMed  Google Scholar 

  • Fowler ZL, Shah K, Panepinto JC, Jacobs A, Koffas MAG (2011) Development of non-natural flavanones as antimicrobial agents. PLoS One 6:1–5

    Google Scholar 

  • Gordon RJ, Campbell J, Henderson DK, Henry DCR, Swart RM, Tasker PA, White FJ, Wood JL, Yellowlees LJ (2008) Polyacidic multiloading metal extractants. Chem Commun 4801–4803

  • Haraguchi H, Tanimoto K, Tamura Y, Mizutani K, Kinoshita T (1998) Mode of antibacterial action of retrochalcones from Glycyrrhiza inflata. Phytochemistry 48:125–129

    Article  CAS  PubMed  Google Scholar 

  • Hwang D, Hyun J, Jo G, Koh D, Lim Y (2011) Synthesis and complete assignment of NMR data of 20 chalcones. Magn Reson Chem 49:41–45

    Article  CAS  PubMed  Google Scholar 

  • Kromann H, Larsen M, Boesen T, Schonning K, Nielsen SF (2004) Synthesis of prenylated benzaldehydes and their use in the synthesis of analogues of licochalcone A. Eur J Med Chem 39:993–1000

    Article  CAS  PubMed  Google Scholar 

  • Linday ME (1962) Practical introduction to microbiology. E and F.N. Spon Ltd., London 177

    Google Scholar 

  • Mandge S, Singh HP, Gupta SD, Moorthy NSHN (2007) Synthesis and characterisation of some chalcone derivatives. Tren Appl Sci Res 2:5256

    Google Scholar 

  • Marais JPJ, Deavours B, Dixon RA, Ferreira D (2006) In: Grotewold E (ed) The science of flavonoids. Springer, New York, pp 1–46

    Chapter  Google Scholar 

  • Nowakowska Z (2007) A review of anti-infective and anti-inflammatory chalcones. Eur J Med Chem 42:125–137

    Article  CAS  PubMed  Google Scholar 

  • Pouramini Z, Moradi A (2012) Comparing of 5-nonylsalicylaldoxime and salicylaldehyde characterisation using magnesium salt formylation process. J Korean Chem Soc 56:357–362

    Article  CAS  Google Scholar 

  • Sperline RP, Song Y, Ma E, Freiser H (1998) Organic constituents of cruds in Cu solvent extraction circuits. II. Photochemical and acid hydrolytic reactions of alkaryl hydroxyoxime reagents. Hydrometallurgy 50:23–38

    Article  CAS  Google Scholar 

  • Stapleton PD, Shah S, Hamilton-Miller JMT, Hara Y, Nagaoka Y, Kumagai A, Uesato S, Taylor PW (2004) Anti-staphylococcus aureus activity and oxaxillin resistance modulating capacity of 3-O-acyl-catechins. Int J Antimicrob Agents 24:374–380

    Article  CAS  PubMed  Google Scholar 

  • Yoon H, Eom S, Hyun J, Jo G, Hwang D, Lee S, Yong Y, Park JC, Lee YH, Lim Y (2011) 1H and 13C NMR data on hydroxy/methoxy flavonoids and the effects of substituents on chemical shifts. Bull Korean Chem Soc 32:2101–2104

    Article  CAS  Google Scholar 

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Acknowledgments

We are highly thankful to the Director, CSIR-IICT, Hyderabad, India for support and encouragement.

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Correspondence to Uppuluri Venkata Mallavadhani.

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Mallavadhani, U.V., Sahoo, L., Kumar, K.P. et al. Synthesis and antimicrobial screening of some novel chalcones and flavanones substituted with higher alkyl chains. Med Chem Res 23, 2900–2908 (2014). https://doi.org/10.1007/s00044-013-0876-x

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  • DOI: https://doi.org/10.1007/s00044-013-0876-x

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