SYNTHESIS, CHARACTERIZATION, ANTIMICROBIAL AND ANTIOXIDANT ACTIVITIES OF SUBSTITUTED PYRAZOLINES FROM FURYL-FLUORENYL CHALCONE

M. Nagoor Meeran; C. Hazarathaiah Yadav; A. Zahir Hussain

doi:10.22159/ijap.2022.v14ti.47

Authors

M. Nagoor Meeran Department of Chemistry, Vel Tech Rangarajan Dr. Sagunthala R and D Institute of Science and Technology (Deemed University), Avadi, Chennai, Tamil Nadu 600062, India
C. Hazarathaiah Yadav Department of Chemistry, Vel Tech Rangarajan Dr. Sagunthala R and D Institute of Science and Technology (Deemed University), Avadi, Chennai, Tamil Nadu 600062, India
A. Zahir Hussain PG and Research Department of Chemistry, Jamal Mohamed College, Trichy, Tamilnadu 620020, India

DOI:

https://doi.org/10.22159/ijap.2022.v14ti.47

Keywords:

Pyrazolines, Chalcone, Antioxidant, Antimicrobial, NMR

Abstract

Objective: Pyrazolines are nitrogen-containing heterocyclic compounds with five-membered rings. They are fairly widely known, which is what sparked people's interest in this area of research to begin with. It has been shown that there are several ways to accomplish their synthesis. It has come to light that a great number of pyrazoline derivatives exhibit a wide variety of biological features.

Methods: The pyrazoline derivatives and the modified chalcone serve as the foundation for this research. Methods such as elemental analysis, infrared spectroscopy, nuclear magnetic resonance (¹H and ¹³C), and mass spectrometry were used in order to analyze the structures of the produced compounds.

Results: The synthesis of chalcone (Furyl-Fluorenyl derivative) and the substituted pyrazolines was successful and analyzed enough by sophisticated techniques including NMR and Mass Spectrometry. The antibacterial and antioxidant capabilities of the compounds that were produced were also investigated and found the significant potential of the compounds.

Conclusion: The antibacterial and antioxidant capabilities of the compounds that were produced were also investigated and found the significant potential of the compounds.

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References

Rudrapal M, Khan J, Dukhyil AAB, Alarousy RMII, Attah EI, Sharma T. Chalcone scaffolds, bioprecursors of flavonoids: chemistry, bioactivities, and pharmacokinetics. Molecules. 2021;26(23):7177. doi: 10.3390/molecules26237177, PMID 34885754.

Raut NA, Dhore PW, Saoji SD, Kokare DM. Selected bioactive natural products for diabetes mellitus. Stud Nat Prod Chem. 2016;48:287-322. doi: 10.1016/B978-0-444-63602-7.00009-6.

Stavenga DG, Leertouwer HL, Dudek B, van der Kooi CJ. Coloration of flowers by flavonoids and consequences of pH dependent absorption. Front Plant Sci. 2020;11:600124. doi: 10.3389/fpls.2020.600124, PMID 33488645.

Dong F, Jian C, Zhenghao F, Kai G, Zuliang L. Synthesis of chalcones via claisen–schmidt condensation reaction catalyzed by acyclic acidic ionic liquids. Cat Commun. 2008;9(9):1924-7. doi: 10.1016/j.catcom.2008.03.023.

Banoth RK, Thatikonda A. A review on natural chalcones an update. Int J Pharm Sci Res. 2019;5:546-55. doi: 10.13040/IJPSR.0975-8232.11(2).546-55.

Jawad AM, Salih MNM, Helal TA, Obaid NH, Aljamali NM. Review on chalcone (preparation, reactions, medical and bio applications). Int J Chem Synth Chem React. 2019;5(1):16-27.

Panda SS, Chowdary PVR, Jayashree BS. Synthesis, antiinflammatory and antibacterial activity of novel indolyl-isoxazoles. Indian J Pharm Sci. 2009;71(6):684-7. doi: 10.4103/0250-474X.59554, PMID 20376225.

Selvakumar D, Venkatesan J, Pandeya S. Synthesis and biological evaluation of 4,6-diaryl substituted-4,5-dihydro-2-amino pyrimidines. Indian J Pharm Sci. 2007;69(4). doi: 10.4103/0250-474X.36954.

BR, Murthy MS, Basha Shaik A. Design, facile synthesis, and biological evaluation of novel 1,3-thiazine derivatives as potential anticonvulsant agents. Asian J Pharm Clin Res 2015;9(5). doi: 10.22159/ajpcr.2016.v9i5.13676.

Sharma A, Khaturia S, Singh HL. Synthesis of new schiff base of 1,3-oxazine and 1,3-Thiazine derivatives derived from 4-phenyl substituted chalcones and evaluation of their antibacterial activity. Asian J Chem. 2021;33(3):531-6. doi: 10.14233/ajchem.2021.23050.

Kavitha R, Nagoor Meeran M, Sureshjeyakumar RP. Synthesis, characterization and antimicrobial activity of substituted pyrazolines. Chem Sci Trans. 2015;4(4):1001-6. doi: 10.7598/cst2015.1118.

Thirunarayanan G, Sekar KG. Solvent-free one-pot cyclization and acetylation of chalcones: synthesis of some 1-acetyl pyrazoles and spectral correlations of 1-(3-(3,4-dimethyl phenyl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazole-1-yl) ethanones. J Saudi Chem Soc. 2016;20(6):661-72. doi: 10.1016/j.jscs.2013.12.002.

Drabu S, Kumar N. Synthesis and biological screening of substituted 2-aminocyanopyridines. Asian J Chem. 2007;19(6):4957-9.

Karthikeyan V, Sivakumar K, Gokuldass A, Mohana Sundaram S. Studies on larvicidal activity of leucas aspera, vitex negundo and eucalyptus against culex quinquefasciatus collected from coovum river of Chennai, India. Asian J Pharm Sci Clin Res. 2012;5(3):1-4.

Venkatesh T, Bodke YD. Synthesis, the antimicrobial and antioxidant activity of chalcone derivatives containing thiobarbitone nucleus. Med Chem Los Angeles. 2016;6(7):7. doi: 10.4172/2161-0444.1000383.

Kaoua R, Bennamane N, Bakhta S, Benadji S, Rabia C, Nedjar Kolli B. Synthesis of substituted 1,4-diazepines and 1,5-benzodiazepines using an efficient heteropolyacid-catalyzed procedure. Molecules. 2010 Dec 28;16(1):92-9. doi: 10.3390/molecules16010092, PMID 21189457, PMCID PMC6259285.

Bhat KI, Kumar A. Synthesis and anti-inflammatory activity of some novel 1,5-benzodiazepine derivatives. Asian J Pharm Clin Res. 2016;9(4):63-6.

Mohanasundaram S, Doss VA, Haripriya G, Varsha M, Daniya S, Madhankumar. GC-MS analysis of bioactive compounds and comparative antibacterial potentials of aqueous, ethanolic and hydroethanolic extracts of Senna alata L. against enteric pathogens. Int J Res Pharm Sci. 2017;8(1):22-7.

Biswajit D. Pyrazoline hydroxylic [review]. IJPSR. 2016;12(6):2570-88. doi: 10.13040/IJPSR.0975-8232.12(5).2570-88.

Yusuf M, Jain P. Synthetic and biological studies of pyrazolines and related heterocyclic compounds. Arab J Chem. 2014;7(5):553-96. doi: 10.1016/j.arabjc.2011.09.013.

Mohanasundaram S, Rangarajan N, Sampath V, Porkodi K, Dass Prakash MV, Monicka N. GC-MS identification of anti-inflammatory and anticancer metabolites in edible milky white mushroom (Calocybe indica) against human breast cancer (MCF-7) cells. Res J Pharm Technol. 2021;14(8):4300-6.

Jain SK, Singhal R. A review on pyrazoline derivatives as antimicrobial agent. Int J Pharm Pharm Sci 2020;12:15-24. doi: 10.22159/ijpps.2020v12i6.37456.

Patel MR, Dodiya BL, Ghetiya RM, Joshi KA, Vekariya PB, Bapodara AH. Synthesis and antimicrobial evaluation of pyrazoline derivatives. Int J Chem Tech Res. 2011;3(2):967-74.

Mohanasundaram S, Doss VA, Maddisetty P, Magesh R, Sivakumar K, Subathra M. Pharmacological analysis of a hydroethanolic extract of Senna alata (L.) for in vitro free radical scavenging and cytotoxic activities against Hep G2 cancer cell line. Pak J Pharm Sci. 2019;32(3):931-4.

Kumar AK, Jayaroopa P. Pyrazoles: synthetic strategies and their pharmaceutical application-an overview. Int J Pharm Tech Res. 2013;5(4):1473-86.

Kumar AK, Pyrazolines GM. Versatile molecules of synthetic and pharmaceutical applications-a review. Int J Chem Tech Res. 2015;8(1):313-22.

Surendra Kumar R, Arif IA, Ahamed A, Idhayadhulla A. Anti-inflammatory and antimicrobial activities of novel pyrazole analogues. Saudi J Biol Sci. 2016;23(5):614-20. doi: 10.1016/j.sjbs.2015.07.005. PMID 27579011.

Revanasiddappa BC, Kumar MV, Kumar H. Synthesis and antioxidant activity of novel pyrazoline derivatives. Hygeia JD Med 2018;10(1):43-9. doi: 10.15254/H.J.D.Med.10.2018.177.

Patel P, Gor D, Patel PS. Design, synthesis and pharmacological evaluation of new series of pyrazolines based thiazolidine-4-one derivatives. Chem Sci Trans. 2016;2(4):1089-93.

Rahaman SA, Ragjendra Prasad Y, Bhuvaneswari K, Phani K. Synthesis and antihistaminic activity of novel pyrazoline derivatives. Int J Chem Technol Research. 2010;2(1):16-20.

Mohanasundaram S, Rangarajan N, Sampath V, Porkodi K, Pennarasi M. GC-MS and HPLC analysis of antiglycogenolytic and glycogenic compounds in kaempferol 3-O–gentiobioside containing senna alata L. leaves in experimental rats. Translational Metab Syndr Research. 2021;4:10-7.

Slilveri S, Basaboina N, Vamaraju HB, Raj S. Design, synthesis, molecular docking, ADMET studies and biological evaluation of pyrazoline incorporated 1,2,3 triazole benzene sulphonamides. Int J Pharm Pharm Sci. 2019;11:6-15.

Rangarajan N, Sangeetha R, Mohanasundaram S, Sampath, Porkodi K, Dass Prakash MV. Additive inhibitory effect of the peels of citrus limon and citrus sinensis against amylase and glucosidase activity. IJRPS 2021;11(4):6876-80. doi: 10.26452/ijrps.v11i4.3661.

Sadashiva R, Naral D, Kudva J, Madan Kumar S, Byrappa K, Mohammed Shafeeulla R. Synthesis, structure characterization, in vitro and in silico biological evaluation of a new series of thiazole nucleus integrated with pyrazoline scaffolds. J Mol Struct. 2017;1145:18-31. doi: 10.1016/j.molstruc.2017.05.066.

Ahmad A, Husain A, Khan SA, Mujeeb M, Bhandari A. Synthesis, antimicrobial and antitubercular activities of some novel pyrazoline derivatives. J Saudi Chem Soc. 2016;20(5):577-84. doi: 10.1016/j.jscs.2014.12.004.

Sankar A, Pandimuthu G, Nithya G, Ravikumar R, Meeran NM. Synthesis, characterization and antimicrobial activity of substituted pyrazole-based heterocyclic compounds. Pharm Chem. 2016;8(19):345-9.

Meeran MN, Hussain AZ. Synthesis, characterization and DPPH scavenging assay of isatin-related spiro heterocyclic compounds. Indian J Pharm Sci. 2017;79(4):641-5. doi: 10.4172/pharmaceutical-sciences.1000273.