Synthesis, Characterization and Evaluation of Antibacterial and Antioxidant Activities of some New Series of Chalcones (?, ?’-Bis (Substitutedarylidene)-?-Ethylcyclohexanones) Derivatives
Keywords:Chalcones, Antioxidant Activity, Α, Β-Unsaturated Ketones
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.
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.
We, the undersigned, give an undertaking to the following effect with regard to our article entitled
________________________________________________________________________________” submitted for publication in (Journal title)________________________________________________ _______________________________________________________Vol.________, Year _________:-
1. The article mentioned above has not been published or submitted to or accepted for publication in any form, in any other journal.
2. We also vouchsafe that the authorship of this article will not be contested by anyone whose name(s) is/are not listed by us here.
3. I/We declare that I/We contributed significantly towards the research study i.e., (a) conception, design and/or analysis and interpretation of data and to (b) drafting the article or revising it critically for important intellectual content and on (c) final approval of the version to be published.
4. I/We hereby acknowledge ADRs conflict of interest policy requirement to scrupulously avoid direct and indirect conflicts of interest and, accordingly, hereby agree to promptly inform the editor or editor's designee of any business, commercial, or other proprietary support, relationships, or interests that I/We may have which relate directly or indirectly to the subject of the work.
5. I/We also agree to the authorship of the article in the following sequence:-
Authors' Names (in sequence) Signature of Authors
1. _____________________________________ _____________________________________
2. _____________________________________ _____________________________________
3. _____________________________________ _____________________________________
4. _____________________________________ _____________________________________
5. _____________________________________ _____________________________________
6. _____________________________________ _____________________________________
7. _____________________________________ _____________________________________
8. _____________________________________ _____________________________________
(I). All the authors are required to sign independently in this form in the sequence given above. In case an author has left the institution/ country and whose whereabouts are not known, the senior author may sign on his/ her behalf taking the responsibility.
(ii). No addition/ deletion/ or any change in the sequence of the authorship will be permissible at a later stage, without valid reasons and permission of the Editor.
(iii). If the authorship is contested at any stage, the article will be either returned or will not be
processed for publication till the issue is solved.