Synthesis, characterization, mesomorphic and biological evaluation of some novel sulphonamide Schiff base derivatives

• Authors: Rana Jatin R. , Vijay B. Patel , Nikhil K. Agarwal , Vinay S. Sharma , Rakesh Gothwal , Bhavesh Sharma
• Languages of publication: EN

Abstracts

EN

A Novel series of sulphonamide schiff base compounds obtained from sulfa drugs were synthesized by the reaction of 2,4-dichloro-5-sulfamoylbenzoic acid with aldehydes. The synthesized compounds were characterized by using FT-IR, Mass, 1H NMR and 13C NMR spectroscopy to confirm the chemical structures of synthesized compounds. The sulphonamide Schiff base compounds were tested for anti-bacterial, anti-fungal and anti-malarial evaluation. The biological activity of synthesized compounds was evaluated by assessing the inhibitory concentration (IC) by measuring their inhibition zone versus certain kinds of standard antibiotics. Noticeably, compound NV5 was the most potent compound in-vitro anti-microbial (S. aureus) with a MTCC value of 96 microgram/ml in comparison with Ampicillin and compounds NV9 and NV11 showed good activity in-vitro anti-fungal (C. albicans) with a MTCC value of 277 microgram/ml. Similarly, compound NV6 showed high potent activity of anti-malarial (P. falciparum) with mean IC50 value as compared to other synthesized derivatives. Addition to this, two of selected compounds showed liquid crystalline properties.

Keywords

EN

Anti-bacterial; Anti-fungal; Anti-malarial; Schiff base; Sulfonamide

Discipline

• CHEMISTRY: CHEMISTRY

• Publisher: Scientific Publishing House „DARWIN”
• Journal: World Scientific News
• Year: 2022
• Volume: 163
• Pages: 1-15

Contributors

author

Rana Jatin R.

• Department of Chemistry, Faculty of Basic and Applied Science, Madhav University, Rajasthan, India

author

Vijay B. Patel

• Department of Chemistry, Faculty of Basic and Applied Science, Madhav University, Rajasthan, India

author

Nikhil K. Agarwal

• Department of Chemistry, Faculty of Basic and Applied Science, Madhav University, Rajasthan, India

author

Vinay S. Sharma

• Department of Chemistry, Faculty of Basic and Applied Science, Madhav University, Rajasthan, India

author

Rakesh Gothwal

• Department of Bioscience, Faculty of Basic and Applied Science, Madhav University, Rajasthan, India

author

Bhavesh Sharma

• Shri Jagdish Prasad Jhabermal Tiberwala University, Rajasthan, India

References

• [1] Hopkins, M.D.; Abebe, F.A.; Scott, K.A.; Ozmer, G.L. Synthesis and identification of heteroaromatic N-benzyl sulfonamides as potential anticancer agents. Org. Biomol. Chem. 2019, 17, 8391-8402. https://doi.org/10.1039/C9OB01694E
• [2] Mahapatra, D.K.; AsatI, V.; Bharti, S.K. An Updated Patent Review of Therapeutic Applications of Chalcone Derivatives, Expert Opin Ther Pat 2019, 29(5), 385-406. https://doi.org/10.1080/13543776.2019.1613374
• [3] Silva, D., C. M. 2011. Schiff bases: A short review oftheir antimicrobial activities. Journal of Advanced Research 2011, 2(1), 1–8. https://doi.org/10.1016/j.jare.2010.05.004
• [4] Li,Y.; Yang, Z.S.; Zhang, H.; Cao, B.J.; Wang, F.D. Artemisinin derivatives bearing Mannich base group: synthesis and antimalarial activity. Bio Org and Med Chem 2003, 11, 4363-4368. https://doi.org/10.1016/S0968-0896(03)00499-1
• [5] Jesmin, M., Ali, M. M., Khanam, J. A. Antitumouractivities of some schiff bases derived from benzoin,salicylaldehyde, amino phenol and 2, 4 dinitrophenylhydrazine. Thai Journal of Pharmaceutical Sciences 2010, 34(1), 20-31
• [6] Al-Garawi, Z. S. M., Tomi, I. H. R., Al-Daraji, A. H. R. Synthesis and characterization of newamino acid-Schiff bases and studies their effectson the activity of ACP, PAP and NPA enzymes. Journal of Chemistry 2012, 9(2), 962-969. https://doi.org/10.1155/2012/218675
• [7] Sahu, R., Thakur, D. S., Kashyap, P. Schiff base:An overview of its medicinal chemistry potentialfor new drug molecules. Int. J. Pharm. Sci. Nanotech 2012, 5, 1757-1764. https://doi.org/10.37285/ijpsn.2012.5.3.2
• [8] Jarrahpour, A. Computational evaluation andexperimental in vitro antibacterial, antifungal andantiviral activity of bis-Schiff bases of isatin andits derivatives. Medicinal Chemistry Research 2013, 22(3), 1203-1211. https://doi.org/10.37285/ijpsn.2012.5.3.2
• [9] Kulkarni, A. A. Synthesis, characterization andbiological behavior of some Schiff’s and Mannichbase derivatives of Lamotrigine. Arabian Journal of Chemistry 2017, 10, 184-189. https://doi.org/10.1016/j.arabjc.2012.07.020
• [10] Hou, Z.; Li, C.; Liu, Y. Et al. Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II. Journal of Enzyme Inhibition and Medicinal Chemistry 2020, 35, 383-390. https://doi.org/10.1080/14756366.2019.1705293
• [11] Melagraki, G.; Afantitis, A.; Sarimveies, H. et al. QSAR study on para-substituted aromatic sulfonamides as carbonic anhydrase II inhibitors using topological information indices. Bioorganic & Medicinal Chemistry, 2006, 14, 1108-1114. https://doi.org/10.1016/j.bmc.2005.09.038
• [12] Bilginer, S.; Gonder, B.; Gul, H.I.; Kaya, R. Novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase I and II inhibitory properties. Journal of Enzyme Inhibition and Medicinal Chemistry, 2020, 35, 325-329. https://doi.org/10.1080/14756366.2019.1700240
• [13] Ali, E.M.H.; Abdel, M.S.; Ammar, U.M. Design, synthesis, and biological evaluation of novel imidazole derivatives possessing terminal sulphonamides as potential BRAFV600E inhibitors. Bioorganic Chemistry, 2021, 104508. https://doi.org/10.1016/j.bioorg.2020.104508
• [14] Mondol, D.; Pal, G.; Chowdhury, C. Palladium(0)-catalysed regioselective cyclisations of 2-amino(tosyl) benzamides/sulphonamides: the stereoselective synthesis of 3-ylidene-[1,4]benzodiazepin-5-ones/benzo[f][1,2,5]thiadiazepine-1,1-dioxides. Chem. Commun 2021, 57, 5462-5465. https://doi.org/10.1039/D1CC00793A
• [15] Obayes, H.R.; Al-Amiery, A. A.; Alwan, G.H. Sulphonamides as corrosion inhibitor: Experimental and DFT studies. J. Mol. Struc. 2017, 1138, 27-34. https://doi.org/10.1016/j.molstruc.2017.02.100
• [16] Weyesa, A.; Mulugeta, E. Recent advances in the synthesis of biologically and pharmaceutically active quinoline and its analogues: a review. RSC Adv. 2020, 10, 20784-20793. https://doi.org/10.1039/D0RA03763J
• [17] Harry, N.A.; Ujwaldev, S.M.; Gopinathan, A. Recent advances and prospects in the metal-free synthesis of quinolines. Org. Biomol. Chem. 2020, 18, 9775-9790. https://doi.org/10.1039/D0OB02000A
• [18] Sharma, V.S.; Patel, R.B. Effect of alkyl chain in the terminal ester group on mesomorphic properties of new rod like homologous series: Synthesis and characterization. Mol. Cryst. Liq. Cryst. 2017, 643, 62-75. https://doi.org/10.1080/15421406.2016.1262690
• [19] Sharma, V.S.; Patel, R.B. Synthesis and mesomorphic properties of new chalconyl-linkage-based liquid crystal compounds: The effect of flexibility. Mol. Cryst .Liq. Cryst. 2017, 643, 129-140. https://doi.org/10.1080/15421406.2016.1263112
• [20] Sharma, V.S.; Patel, R.B. Study the effects of terminal side chain and –nitro group on mesomorphic behaviour of cinnamate-chalconyl based liquid crystal. Mol. Cryst. Liq. Cryst. 2017, 643, 1-12. https://doi.org/10.1080/15421406.2016.1262672
• [21] Sharma, V.S.; Patel, R.B. Mesomorphic study of novel chalconyl-ester-based nonisomeric series: Synthesis and characterization. Mol. Cryst. Liq. Cryst. 2017, 643, 13-27. https://doi.org/10.1080/15421406.2016.1262680
• [22] Sharma, V.S.; Patel, R.B. Tuning the mesomorphic properties of nonisomeric chalconyl-ester bases homologous series: The effect of tail group. Mol. Cryst. Liq. Cryst 2017, 643, 40-51. https://doi.org/10.1080/15421406.2016.1262686
• [23] Ooi, Y.H., Yeap, G.Y., Takeuchi, D., Synthesis, mesomorphic properties and structural studies on 1,3,5-trisubstituted benzene-based star-shaped derivatives containing Schiff base ester as the peripheral arm. Journal of Molecular Structure. 2013, 1051, 361-375. https://doi.org/10.1016/j.molstruc.2013.08.015
• [24] Ha, S.T., Onga, L.K., Wan Wong, J.P., Yeap, G.Y., Linc, H.C., Onga, S.T. and Koh, T.M. Mesogenic Schiff's base ether with dimethylamino end group. Phase Transitions 2009, 82, 387-397. https://doi.org/10.1080/01411590902957449
• [25] Thaker, B.T. and Patel, P. Synthesis and Characterization of Liquid Crystalline Materials Incorporating the Novel 4-Amino-1,2,4-triazole and Isonicotinic Acid Hydrazide Moiety. Mol. Cryst. Liq. Cryst., 2008, 482, 3-20. https://doi.org/10.1080/15421400801915050
• [26] Yeap, G.Y., Ha, S.T., Boey, P.L., Mahmood, W.A.K. Synthesis and Characterization of Some New Mesogenic Schief Base Esters N-[4-(4-n-Hexadecanoyloxybenzoyloxy)-Benzylidene]-4-Substituted Anilines. Mol. Cryst. Liq. Cryst. 2006, 452, 73-90. https://doi.org/10.1080/15421400500382156
• [27] Ashok N. Patange, Uttam M. Yadav, Pratik A. Desai, Pravin U. Singare, Synthesis of some Novel Halogenated Platinum (II) Complexes of Active Schiff’s Base Ligand Derived from 5-Bromo Isatin and Evaluation of their Antibacterial Activity. World Scientific News 10 (2015) 32-43
• [28] Devang N. Mokariya, Rasik M. Tejani, Juvansinh J. Jadeja, Manish K. Shah, Synthesis, characterization and anti-bacterial activity of mix ligand complexes of copper with isonicotinic acid and different N-donor ligands. World Scientific News 146 (2020) 95-109
• [29] Surbhi V. Upadhyay, Raksha V. Zala, Keyur D. Bhatt, Synthesis, characterization, biological activity of Schiff bases derived from 2-bromo-4-methyl aniline and its potentiometric studies with Cu(II), Co(II) and Ni(II) ions. World Scientific News 145 (2020) 1-15
• [30] E. Ogbonda-Chukwu, O. J. Abayeh, O. Achugasim, O. C. Eruteya, Synthesis and antimicrobial studies of structurally-related Schiff bases and their metal complexes. World Scientific News 160 (2021) 16-36
• [31] Kadachha Raju Ramade, Atul J. Rojivadiya, Yogesh T. Naliapara, Jayesh S. Babariya, Synthesis and characterization of novel pyrimidine derivatives of N-pentyl-2,7-diphenyl-3,8a-dihydroimidazo[1,2-a]pyrimidin-3-amine via 4-phenylpyrimidin-2-amine. World News of Natural Sciences 37 (2021) 92-101
• [32] Joshi A.K., D. M. Purohit, Synthesis and antimicrobial activity of 5-(2’-n-butyl-4’-chloro-1’-H-imidazol-5’-yl)-3-aryl-4,5-dihydro-{1-H/1-acetyl/1-phenyl}-pyrazoles. World News of Natural Sciences 35 (2021) 38-47

• Document Type: article