Abstract
Chalcones were synthesized by reaction of 3-acetyl-2,5-dimethylfuran with corresponding active aldehyde in ethanolic NaOH. The structure of these compounds was established by elemental analysis, IR, 1H-NMR, 13C-NMR and EI-MS spectral analysis. UV–vis and fluorescence spectroscopy measurements provided that compounds are good absorbent and fluorescent. Fluorescence polarity study demonstrated that the compounds were sensitive to the polarity of the microenvironment provided by deferent solvents. In addition, spectroscopic and physicochemical parameters, including electronic absorption, extenction coefficient, Stokes shift, oscillator strength and transition dipole moment were investigated in order to explore the analytical potential of synthesized compounds. The anti-bacterial activity of the compounds were first tested in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria, and then the minimum inhibitory concentration (MIC) was determined with the reference of standard drug Tetracycline. The results showed that compound 3 is better inhibitors of both types of the bacteria (Gram-positive and Gram-negative) as compared to tetracycline.
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Asiri AM, Khan SA, Al-Amodi MS, Alamry KA (2012) Synthesis, characterization absorbance, fluorescence and non linear optical properties of some donor acceptor chromophores. Bull Kor Chem Soc 33:1900–1906
Marwani HM, Asiri AM, Khan SA (2013) Spectral, stoichiometric ratio, physicochemical, polarity and photostability studies of newly synthesized chalcone dye in organized media. J Lumin 136:296–302
Asiri AM, Khan SA, Hallag SI (2011) Electrochemical studies of some carbazole derivatives via cyclic voltammetry and convolution - deconvolution transforms. J New Mater Electrochem Syst 14:251–258
Asiri AM, Khan SA (2011) Synthesis, characterization and optical properties of mono- and bis-chalcone. Mater Lett 65:1749
Mai CM, Yaeghoobi M, Abd-Rahman N, Kang YB, Pichika MR (2014) Chalcones with electron-withdrawing and electron-donating substituents: anticancer activity against TRAIL resistant cancer cells, structure–activity relationship analysis and regulation of apoptotic proteins. Eur J Med Chem 77:378–387
Bandgar BP, Gawande SS, Bodade RG, Totre JV, Khobragade CN (2010) Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, −anti-inflammatory and antioxidant agents. Bioorg Med Chem 18:1364–1370
Cheng J, Hung C, Yang S, Wang J, Won S, Lin C (2008) Synthesis and cytotoxic, anti-inflammatory, and anti-oxidant activities of 2′,5′-dialkoxylchalcones as cancer chemopreventive agents. Bioorg Med Chem 16:7270–7276
Parveen H, Hayat F, Salahuddin A, Azam A (2010) Synthesis, characterization and biological evaluation of novel 6-ferrocenyl-4-aryl-2-substituted pyrimidine derivatives. Eur J Med Chem 45:3497–3503
Asiri AM, Khan SA (2012) Synthesis, characterization, and in vitro antibacterial activities of macromolecules derived from bis-chalcon. J Heterocycl Chem 49:1434–1438
Yesuthangam Y, Pandian S, Venkatesan K, Gandhidasan R, Murugesan R (2011) Photogeneration of reactive oxygen species and photoinduced plasmid DNA cleavage by novel synthetic chalcones. J Photochem Photobiol B 102:200–208
Khan SA, Razvi MAN, Bakry AH, Afzal SM, Asiri AM, El-Daly SA (2015) Photogeneration of reactive oxygen species and photoinduced plasmid DNA cleavage by novel synthetic chalcones. Spectrochim Acta Part A 137:1100–1105
Schraub M, Kim H, Hampp N (2014) Photoinduced refractive index changes of 3-phenyl-coumarin containing polymers for ophthalmic applications. Eur. Polym J 51:21–27
Fayed TA, Awad MK (2004) Dual emission of chalcone-analogue dyes emitting in the red region. Chem Phys 303:317–326
Devi JM, Tharmaraj P, Ramakrishnan SK, Ramachandran K (2008) On the thermal properties of metal (II) complexes of chalcone. Mater Lett 62:852–856
Gaber M, El-Daly SA, Fayed TA, El-Sayed YS (2008) Photophysical properties, laser activity and photoreactivity of a heteroaryl chalcone: a model of solvatochromic fluorophore. Opt Laser Technol 40:528–537
El-Daly SA, Asiri AM, Khan SA, Alamry KA (2013) Spectral Properties and Micellization of 1-(2, 5-Dimethyl-thiophen-3-yl)-3-(2, 4, 5-trimethoxy-phenyl)-propenone (DTTP) in different media. J Lumin 134:819–824
Agilent CrysAlis PRO (2012). Agilent Technologies, Yarnton, England
Sheldrick GM (2008) A short history of SHELX. Acta Crystallogr A64:112–122
Barbour LJ, Seed X (2001) A software tool for supramolecular crystallography. J Supramol Chem 1:189
Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, Streek JV (2006) Mercury: visualization and analysis of crystal structures. J Appl Crystallogr 39:453–457
Farrugia LJ (2012) WinGX and ORTEP for Windows: an update. J Appl Crystallogr 45(2012):849–854
Spek AL (2009) Structure validation in chemical crystallography. Acta Crystallogr D65:148–155
Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H (2009) OLEX2: a complete structure solution, refinement and analysis program. J Appl Crystallogr 42:339–341
Asiri AM, Akkurt M, Khan SA, Arshad MN, Khan IU, Sharif HMA (2009) 2-Benzenesulfonamidobenzoic acid. Acta Crystallogr E65:1246–1247
Asiri AM, Marwani HM, Alamry KA, Al-Amoudi MS, Khan SA, El-Daly SA (2014) Green synthesis, characterization, photophysical and electrochemical properties of bis-chalcones. Int J Electrochem Sci 9:799–809
Lippert E (1957) Spectroscopic determinations of the dipole moment of aromatic compounds in the first excited singlet state. Z Elektrochem 61:962–975
Dey JK, Dogra SK (1991) Solvatochromism and Prototropism in 2-(Aminophenyl) Benzothiazoles. Bull Chem Soc Jpn 64:3142–3152
Acree WE, Wilkins DC, Tucker SA, Griffin JM, Powell JR (1994) Spectrochemical investigations of preferential solvation. 2. compatibility of thermodynamic models versus spectrofluorometric probe methods for tautomeric solutes dissolved in binary mixtures, excited-state dipole moments of some hydroxycoumarin dyes using an efficient solvatochromic method based on the solvent polarity parameter, E T N. J Phys Chem 98:2537–2544
Kumar S, Rao VC, Rastogi RC (2001) Excited state dipole moments from an efficient analysis of solvatochromic stokes shift data. Spectrochim Acta A 57:41–47
Ravi M, Samanta A, Radhakrishnan TP (1994) Excited state dipole moments from an efficient analysis of solvatochromic stokes shift data. J Phys Chem 98:9133–9136
Ravi M, Soujanya T, Samanta A, Radhakrishnan TP (1995) Excited-state dipole moments of some coumarin dyes from a solvatochromic method using the solvent polarity parameter, E N T. J Chem Soc Faraday Trans 91:2739–2742
Turro NJ (1995) Molecular photochemistry (frontiers in chemestry), 1st edn. W. A. Benjamin, Inc, Reading, p 286
Coe BJ, Harris JA, Asselberghs I, Clays K, Olbrechts G, Persoons A, Hupp JT, Johnson RC, Coles SJ, Hursthouse MB, Nakatani K (2002) Quadratic nonlinear optical properties of N-aryl stilbazolium dyes. Adv Funct Mater 12:110–116
Khan SA, Asiri AM (2013) Synthesis of novel pyrazole containing Schiff base derivatives as antibacterial agents on the bases of in-vitro and DFT. Eur J Chem 4:454–458
Acknowledgments
This Project was funded by the King Abdulaziz City for Science and Technology (KACST) through National Science, Technology and Innovation Plan (NSTIP) under grant number 8-ENE198-3. The authors, therefore, acknowledge with thanks KACST for support for Scientific Research. Also, the authors are thankful to the Deanship of Scientific Research (DSR), King Abdulaziz University for their technical support.
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Khan, S.A., Asiri, A.M. & Basisi, H.M. Synthesis, Single X-ray Crystal, Spectroscopic and Photophysical Studies of Novel Heterocyclic Chalcones with Their Biological Application. J Fluoresc 25, 825–834 (2015). https://doi.org/10.1007/s10895-015-1543-z
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DOI: https://doi.org/10.1007/s10895-015-1543-z