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[An Official Publication of ISF College of Pharmacy, Moga]



Original Article
Year : 2019   |  Volume : 11   |  Issue : 4   |  Page : 128-130  

Some chalcone derivatives as antimicrobial agents: Synthesis and characterization

Ashok Maddheshiya, Pooja Chawla

Correspondence Address:Department of Pharmaceutical Chemistry, B.B.D.N.I.T.M., Lucknow, Department of Pharmaceutical Chemistry, ISF College of Pharmacy, Moga

Source of Support: Nil, Conflict of Interest: None Declared


DOI: 10.4103/2231-4040.197331

Abstract  

Substituted chalcones were synthesized by condensing benzaldehyde derivatives with acetophenone derivatives in dilute ethanolic sodium hydroxide solution at room temperature according to Claisen–Schmidt condensation. In the presence of NaOH/EtOH as a catalyst, various substituted chalcones are synthesized. The reaction is clean with excellent yield. The structures of the synthesized compounds were confirmed by IR and mass spectroscopy.

Keywords: Chalcone, Claisen–Schmidt condensation, aldehydes, antimicrobial

How to cite this article:
MaddheshiyaA, Chawla P. Some chalcone derivatives as antimicrobial agents: Synthesis and characterization. Pharmaspire 2019;11(4):128-130.

INTRODUCTION

Chalcones are a group of compounds with various substitution patterns on the two aromatic rings of 1, 3-diphenyl-2-propen-1-one. Chalcones constitute an important class of natural products belonging to the flavonoid family and are reported to possess a wide spectrum of biological activities, including antibacterial, antifungal, anti-inflammatory, antitumor, insect antifeedant, analgesic, anti-mutagenic,[1-3] antiplatelet,[4] antiulcerative,[5] antitubercular,[6] immunomodulatory,[7] antihyperglycemic,[8] antimalarial,[9] anticancer,[10] antiviral,[11] antileishmanial,[12] antioxidant,[13] inhibition of chemical mediators release,[14] inhibition of leukotriene B4,[15] inhibition of tyrosinase,[16] and inhibition of aldose reductase[17] activities. The presence of a reactive α, β-unsaturated ketone function in chalcones was found to be responsible for their antimicrobial activity.
Chemically, they consist of open chain flavonoids in which the two aromatic rings are joined by a three carbon α, β-unsaturated carbonyl system. The presence of a reactive α, β-unsaturated keto function in chalcones is found to be responsible for their antimicrobial activity. In recent years, a variety of chalcones have been reviewed for their cytotoxic, anticancer chemopreventive, and mutagenic as well as antiviral, insecticidal, and enzyme inhibitory properties.[18,19]
Several strategies for the synthesis of these systems, based on the formation of carbon-carbon bond were reported. Among them the direct aldol condensation and Claisen-Schmidt condensation still occupy prominent positions. The main method for the synthesis of chalcones was the classical Claisen-Schmidt condensation in the presence of aqueous alkaline bases,[20] Ba(OH)2,[21] and LiOH microwave irradiation and ultrasound irradiation.[22] They are also obtained through Suzuki reaction,[23] Witting reaction, Friedel-Crafts acylation with cinnamoyl chloride, or photo-Fries rearrangement of phenyl cinnamates. In aldol condensation, the preparation of chalcones requires at least two-steps aldol formation and dehydration. Since aldol addition is reversible, mukaiyama, or Claisen-Schmidt condensation approach of using enol ether has emerged as an alternative pathway. A total of five derivatives were synthesized as shown in Scheme 1, Figure 1 and evaluated for antimicrobial activity. Physical characterisation of compounds is shown in Table 1.

Antimicrobial activity

The antimicrobial activity of the synthesized compounds was evaluated using cup-plate method. Ciprofloxacin was used as standard drug. After the application of the inoculum, the plates were incubated for 24 h at temperature 37.5±5°C after that the standard and test samples in appropriate dilutions were applied and incubated for next 24 h at temperature 37.5±5°C, after that zone of inhibition was measured. The outcomes are listed in Table 2.[24]

Experimental

The chemicals required were obtained from HiMedia Chem. Ltd, SD-Fine Ltd. and Sigma-Aldrich Pvt. Ltd and were used as such.
Melting points were determined using open capillary tube melting point apparatus and are uncorrected. Reaction progress was monitored by performing thin-layer chromatography on silica gel G plates, using iodine vapors and UV chamber as visualizing agents. After physical characterization, the compounds were subjected to spectral analysis. IR spectra were recorded in KBr on a SHIMADZU FT/IR-5300. The mass spectra were recorded on a JEOL-SX-102 instrument using ESI. Infrared spectra were taken on Perkin-Elmer AX-1 spectrometer and values are expressed in cm−1.

General procedure: Synthesis of substituted chalcones

Stirred the mixture of substituted acetophenone (0.01 mol) and substituted benzaldehyde (a-j) (0.01 mol) in ethanol (30 ml), with continuous stirring 30% NaOH or KOH(15 ml) was added dropwise. The solution was stirred for 2 h and was left over night. The reaction mixture was precipitated by addition of ice cold water. The precipitate thus obtained was the desired product.[25]

  1. White amorphous solid: IR (KBr) cm−1: (−OH) 3070.46 cm−1, (C=0) 1662.52 cm−1, (C=C) 1608, 1448.44 cm−1, (Ar-NO2) 1529.45, 1352.01 cm−1. Mass: m/z 285.3 (M+).
  2. White amorphous solid: IR (KBr) cm−1: (−OH) 3062.75 cm−1, (C=0) 1660.60 cm−1, (C=C) 1608, 1448.44 cm−1, (Ar-F) 1529.45, 1352.01 cm−1. Mass: m/z 258.4 (M+).
  3. White amorphous solid: IR (KBr) cm−1 : (-OH) 3070.46 cm−1, (C=0) 1662.52 cm−1, (C=C) 1606.59, 1477.37 cm−1, (Ar-Cl) 1080.06 cm−1. Mass: m/z 274.8 (M+).
  4. White amorphous solid: (–OH) 3060.82 cm−1, (C=0) 1658.67 cm−1,(C=C) 1604.66, 1446.51 cm−1, (Ar-Cl) 1091.63 cm−1. Mass: m/z 274.6 (M+).
  5. Yellow amorphous solid: (-OH) 3060.82 cm−1, (C=0) 1658.67 cm−1, (C=C) 1604.66, 1446.51 cm−1, (Ar-Cl) 1091.63 cm−1. Mass: m/z 270.8 (M+).

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ACKNOWLEDGMENTS

The authors are thankful to management of BBDNITM Lucknow for providing necessary infrastructure.

CONCLUSION

Structures of the synthesized substituted chalcones were confirmed from their respective IR and mass-spectrometry studies. From the antimicrobial screening, it was observed that all the compounds exhibited activity against all the organisms employed. The compounds b and e, showed good antibacterial activity due to its electron donating properties whereas d showed moderate to good activity because of substitution on p-position while a and c showed comparatively lesser activity of all.

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