EVALUATION OF NEWLY DESIGNED ISATIN DERIVATIVES AGAINST VARIOUS BACTERIAL SPECIES
DOI:
https://doi.org/10.22159/ajpcr.2023.v16i3.46609Keywords:
Isatin and its derivatives, Antibacterial action, Streptomycin, Zone of inhibitionAbstract
Objective: The main objective of the present research is to develop new isatin derivatives and evaluate their antibacterial properties.
Methods: In this research article, some new spiro derivatives of isatin were synthesized by two different pathways. The chalcones were prepared by the reaction of different acetophenones and isatins through base-catalyzed condensation followed by the addition of acid. The compounds have been characterized by UV-Vis, FT-IR, 1H- Nuclear magnetic resonance (NMR), 13C-NMR, and Mass spectra.
Results: It was found that the compounds exhibited moderate to significant antibacterial action against four various bacterial strains, that is, Gram-negative Klebsiella pneumoniae and Escherichia coli, Gram-positive Bacillus subtilis, and Staphylococcus aureus. The action of all compounds was compared with standard drug, that is, Streptomycin.
Conclusion: It was concluded that all synthesized isatin derivatives are useful for giving antibacterial responses for one or other bacterial strains. Their action was compared with the standard drug and found that ISP1 showed a response that was almost the same as streptomycin’s effects against Salmonella typhi.
Downloads
References
Guzman-Perez A, Wester RT, Allen MC, Brown JA, Buchholz AR, Cook ER, et al. Discovery of zoniporide: A potent and selective sodium-hydrogen exchanger Type 1 (NHE-1) inhibitor with high aqueous solubility. Bioorg Med Chem Lett 2001;11:803-7. doi: 10.1016/s0960- 894x(01)00059-2, PMID 11277524
Amr Ael-G, Abdel-Latif NA, Abdalla MM. Synthesis and antiandrogenic activity of some new 3-substituted androstano[17,16-c]-5’-aryl-pyrazoline and their derivatives. Bioorg Med Chem 2006;14:373-84. doi: 10.1016/j.bmc.2005.08.024, PMID 16182532
Erdmann OL. Untersuchungen uber den Indigo. J Prakt Chem 1840;19:321-62. doi: 10.1002/prac.18400190161
Auguste L. Recherche sur l Indigo. Ann Chim Phys 1840;3:393-434.
Silva JF, Garden SJ, Pinto AC. The chemistry of isatins: A review from 1975 to 1999. J Braz Chem Soc 2001;12:273-324. doi: 10.1590/S0103- 50532001000300002
Chiyanzu I, Hansell E, Gut J, Rosenthal PJ, McKerrow JH, Chibale K. Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain. Bioorg Med Chem Lett 2003;13:3527-30. doi: 10.1016/s0960-894x(03)00756-x, PMID 14505663
Sharma PK, Balwani S, Mathur D, Malhotra S, Singh BK, Prasad AK, et al. Synthesis and anti-inflammatory activity evaluation of novel triazolyl-isatin hybrids. J Enzyme Inhib Med Chem 2016;31:1520-6. doi: 10.3109/14756366.2016.1151015, PMID 27146339
Medvedev A, Buneeva O, Gnedenko O, Fedchenko V, Medvedeva M, Ivanov Y, et al. Isatin interaction with glyceraldehyde-3-phosphate dehydrogenase, a putative target of neuroprotective drugs: Partial agonism with deprenyl. J Neural Transm Suppl 2006;71:97-103. doi: 10.1007/978-3-211-33328-0_11, PMID 17447420
Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, et al. New isatin derivatives and its antioxidant properties. Eur J Med Chem 2010;45:1374-8. doi: 10.1016/j.ejmech.2009.12.035, PMID 20060202
Prakash CR, Raja S, Saravanan G. Design, and synthesis of 4-(1-(4-chlorobenzyl)-2,3-dioxoindolin-5-yl)-1-(4-substituted/ unsubstituted benzylidene) semicarbazide: Novel agents with analgesic, anti-inflammatory and ulcerogenic properties. Chem Lett 2012;23:541-4. doi: 10.1016/j.cclet.2012.03.014
Medvedev A, Igosheva N, Crumeyrolle-Arias M, Glover V. Isatin-role in stress and anxiety. Stress 2005;8:175-83. doi: 10.1080/10253890500342321, PMID 16236622
Justo LA, Durán R, Alfonso M, Fajardo D, Faro LRF. Effects and mechanism of action of isatin, an MAO inhibitor, on in vivo striatal dopamine release. Neurochem Int 2016;99:147-57. doi: 10.1016/j. neuint.2016.06.012, PMID 27374845
Hewawasam PM. A general method for the synthesis of isatin: Preparation of region specifically functionalized isatin from anilines. Tetrahedron Lett 1994;35:7295-306.
Gassman PG, Cue BW Jr., Luh TY. A general method for the synthesis of isatins. J Org Chem 1977;42:1344-8. doi: 10.1021/jo00428a016
Magnus NA, Diseroad WD, Nevill RC, Wepsiec JP. Synthesis of imidazole based p38 MAP (mitogen-activated protein) kinase inhibitors under buffered conditions. Org Proc Res Dev 2006;10:545-56.
Berry A. Procedure and theoretical considerations for testing antimicrobial agent in agar media. In: Corian V, editor. Antibiotics in Laboratory Medicine. 5th ed. United States: Williams and Wilkins; 1991. p. 1-16.
Suresh S, Priyanka B, Maharaj P, Srikanth C, Karthik K, Sammaiah G. Synthesis of benzimidazole-isatin derivatives for analgesic activity. Asian J Pharm Clin Res 2013;6:65-7.
Shibinskaya MO, Lyakhov SA, Mazepa AV, Andronati SA, Turov AV, Zholobak NM, et al. Synthesis, cytotoxicity, antiviral activity, and interferon inducing ability of 6-(2-aminomethyl)-6H-indolo [2, 3-b] quinoxalines. Eur J Med Chem 2010;45:1237-43. doi: 10.1016/j. ejmech.2009.12.014
Chen LR, Wang YC, Lin YW, Chou SY, Chen SF, Liu LT, et al. Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors. Bioorg Med Chem Lett 2005;15:3058-62. doi: 10.1016/j.bmcl.2005.04.027, PMID 15896959
Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, et al. New isatin derivatives with antioxidant activity. Eur J Med Chem 2010;4:1374-8. doi: 10.1016/j.ejmech.2009.12.035, PMID 20060202
Singh A, et al. Synthesis of some novel ethoxyphthalimide derivatives of pyrazolo[3,4-c] pyrazoles. Orient J Chem 2000;16:315.
Azarifar D, Shaebanzadeh M. Microwave-assisted synthesis of some 3,5-arylated 2-pyrazolines. Molecules 2002;7:885-8.
Firdhouse J, Nalini D. Corrosion inhibition of mild steel in acidic media by 5’-phenyl-2’,4’-dihydrospiro[indole-3,3’-pyrazol]-2(1H)-oneA. J Chem 2013;9:1-9.
Von Auwers K, Muller. One-pot rapid and efficient synthesis of new spiro derivatives of 11H-indeno[1,2-b] quinoxalin-11-one, 6H-indeno[1,2-b] pyrido [3,2-e]pyrazin-6-one and isatin-based 2-pyrazolines. Ber Dt Chem Ges 1908;41:4230.
Levai A, Jek J. Synthesis of carboxylic acid derivatives of 2-pyrazolines. Arkivoc 2005;9:344.
Patel VM, Desai KR. Eco-friendly synthesis of fluorine-containing pyrazoline derivatives over potassium carbonate. Arkivoc 2004;1:123-9.
Lévai A, Jeko J. Synthesis of hydroxylated 3,5-diaryl-2-pyrazolines by the reaction of hydroxychalcones with hydrazines. Arkivoc 2005;10:199-205. doi: 10.3998/ark.5550190.0006.a17
Published
How to Cite
Issue
Section
Copyright (c) 2022 Jyoti Sahu
This work is licensed under a Creative Commons Attribution 4.0 International License.
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.