Synthesis, Characterization and Evaluation of Antibacterial and Antioxidant Activities of some New Series of Chalcones (?, ?’-Bis (Substitutedarylidene)-?-Ethylcyclohexanones) Derivatives

Authors

  • Sameer Kumar Research Scholar, Shri Venketshwara University, NH 24 Rajabpur, Gajraula, District Amroha, Uttar Pradesh, India. 
  • Nidhi Srivastava Institute of Pharmacy, Noida Institute of Engineering and Technology, Plot No. - 19, Knowledge Park-II, Greater Noida, U.P., India.
  • Anurag Meerut Institute of Engineering and Technology, NH-58, Baghpat Road Crossing Byepass Road, Meerut-250005, U.P., India.
  • Mohit Gupta School of Pharmaceutical Sciences, IFTM University, Moradabad, U.P., India.

Keywords:

Chalcones, Antioxidant Activity, Α, Β-Unsaturated Ketones

Abstract

In the present work we synthesized some novel Chalcones or ?, ?-unsaturated ketones with an aim to obtain some new potent antibacterial and antioxidant agents. The ?, ?-unsaturated ketones were synthesized by base catalysed Claisen-Schmidt condensation of ketones having ?, ?’ hydrogens with various aldehydes. The new series of ?, ?-unsaturated ketones were synthesized by reacting ?-ethylcyclohexanone with different substituted benzaldehydes. The classes of the synthesized compounds are: ?, ?’-Bis(substitutedarylidene)?-ethylcyclohexanones [1a-h]. The formation of the compounds [1a-h] is indicated by their UV spectra. The functional groups in the compounds [1a-h] are characterized by their IR spectra. The number and positions of protons in the compounds [1a], [1b], [1c], [1d], [1e], [1g] and [1h] are confirmed by their 1H-NMR spectra. The structures of compounds [3a-h] are confirmed by their Mass spectra. The structures of the compounds [1a-h] are further confirmed by their elemental analysis. All the synthesized compounds were screened for their in vitro antibacterial properties against human pathogenic Gram positive and Gram negative bacteria. Ampicillin was used as the standard. The observations reveal that ?,?’-Bis(5-bromo-2-methoxybenzylidene)- ?-ethylcyclohexanone [1c] exhibits highest activity against Staphylococcus aureus. ?,?’Bis(m-chlorobenzylidene)- ?-ethylcyclohexanone [1g] has highest activity against Escherichia coli. All the synthesized compounds were also screened for their antioxidant activity using ascorbic acid as the standard by DPPH method.

How to cite this article: Kumar S, Srivastava N, Anurag. Synthesis, Characterization and Evaluation of Antibacterial and Antioxidant Activities of some New Series of Chalcones (?, ?’-Bis (Substitutedarylidene)?-Ethylcyclohexanones) Derivatives. J Durg Dis Dev 2019; 3(1): 15-22.

References

Kar A. Medicinal Chemistry. New Age International Publishers, New Delhi; 2nd ed 2001.

Hassan MA, Batterjee S, Taib LA. Stereoselective crossedaldol condensation of 3-acetyl-2,5-dimethylthiophene/ furan with aromatic aldehydes in water: Synthesis of (2E)-3-aryl-1-(thien-3-yl)-prop-2-en-1-ones. Ind J Chem 2006; 45B: 1936-41.

Abdel-Rahman AAH, Abdel-Megied AES, Hawata MAM et al. Synthesis and antimicrobial evaluation of some chalcones and their derived pyrazoles, pyrazolines, isoxazolines and 5,6-dihydropyrimidine-2-(1H)-thiones. Monatsch Chem. 2007; 138: 889-97.

Tripathi KD. Essentials of Medical Pharmacology. Jaypee Brothers Medical Publishers (P) Ltd, New Dehli. 5th ed 2003; 210.

Foye WO. Principles of Medicinal Chemistry. Verghese Publishing House, Bombay. 1989. 3rd ed 245.

https://en.wikipedia.org/wiki/Claisen_condensation/ Retrieved on Jan 2018.

https://chem.libretexts.org/Bookshelves/Organic_ Chemistry/Map%3A_Organic_Chemistry_(Smith)/ Chapter_20%3A_Introduction_to_Carbonyl_ Chemistry%3B_Organometallic_Reagents%3B_ Oxidation_and_Reduction/20.15%3A_%CE%B1%2C%C E%B2-Unsaturated_Carbonyl_Compounds/ Retrieved on Jan 2018.

Liu XL, Xu YJ, Go ML. Functionalised chalcones with basic functionalities having antibacterial activity against drug sensitive Staphylococcus aureus. Eur J Med Chem 2007; 1-7.

http://www.iosrjournals.org/iosr-jpbs/papers/Vol12issue4/Version-6/C1204061420.pdf/ Retrieved on Jan 2018.

Halliwell B, Gullteridge.Free radical. A review. Oxford: Clattendam Press. 1991.

Boeck P, Leal PC, Yunes RA et al. Antifungal activity and studies on mode of action of novel xanthoxyline-derived chalcones. Arch Pharm Chem Life Sci 2005; 338: 87-95.

Tomar V, Bhattachargee G, Kumar A. Synthesis and antimicrobial evaluation of new chalcones containing piperazine or 2,5-dichlorothiophene moiety. Bioorg Med Chem Lett 2007; 17: 5321-4.

Harborne JB. The flavonoids, Advances in Research. Chapman and Hall. New York NY. 1988: 329-88.

Downloads

Published

2019-12-24