SYNTHESIS, CHARACTERIZATION, ANTIMICROBIAL AND ANTIOXIDANT ACTIVITIES OF SUBSTITUTED PYRAZOLINES FROM 2-ACETYLFLUORENE BASED CHALCONE

K.E. POORNI; G. GOHULAVANI; VIVEK PANYAM MURALIDHARAN

doi:10.22159/ijap.2022.v14ti.17

Authors

K.E. POORNI Department of Biochemistry, Vivekanandha College of Arts and Sciences for Women (Autonomous), Elayampalayam, Tiruchengode, Tamilnadu, India
G. GOHULAVANI Department of Chemistry, Ethiraj College for Women, Chennai, Tamilnadu, India
VIVEK PANYAM MURALIDHARAN Department of Chemistry, School of Science and Humanities, Vel Tech Rangarajan, Dr. Sagunthala R&D Institute of Science and Technology, Chennai, Tamilnadu, India

DOI:

https://doi.org/10.22159/ijap.2022.v14ti.17

Keywords:

Heterocyclic compounds, Chalcones, Pyrozaline Antimicrobial and Antioxidant activity

Abstract

Objective: The present work is based on the above pyrazoline derivative form heterocyclic substituted chalcone.

Methods: The elemental analysis, IR, ¹H and ¹³C NMR and mass spectrum analyses were used to characterise the structures of the obtained compounds.

Results: The scheme-1 and scheme-2 describe the synthesis of chalcone (thiophene-fluorenyl derivative) and synthesis of substituted pyrazolines respectively. Chalcone has been synthesized from 2-Acetylfluorene, which had been reacted with phenylhydrazine, 4-substituted phenylhydrazine (4-Chloro and 4-Nitro) and 2,4-Dinitrophenylhydrazine to form the substituted pyrazolines (CP01-CP04).

Conclusion: The antimicrobial and antioxidant properties were evaluated on those newly synthesised compounds.

References

Rudrapal M, Khan J, Dukhyil AAB, Alarousy RMII, Attah EI, Sharma T. Chalcone scaffolds, bioprecursors of flavonoids: chemistry, bioactivities, and pharmacokinetics. Molecules. 2021 Nov 26;26(23):7177. doi: 10.3390/molecules26237177, PMID 34885754, PMCID PMC8659147.

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, PMCID PMC7820715.

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.

Verma S, Srivastava AK, Pandey OP. A review on chalcones synthesis and their biological activity. PharmaTutor. 2018;6(2);22-39. doi: 10.29161/PT.

El-Gohary NS. Arylidene derivatives as synthons in heterocyclic synthesis. OALib. 2014;01(2):1-47. doi: 10.4236/oalib.1100367.

Raghavendra KR, Prabhudeva MG, Kumar AD, Kumar KA, Jayadevappa HP. Isoxazoles-A biocompatible radical scavenging agents: citrus juice mediated environmentally benign synthesis and characterization. Asian J Chem. 2020;32(12):2997-3001. doi: 10.14233/ajchem.2020.22871.

solankee A, Lad S, Solankee S, Ghanshyam Petal. Chalcones, pyrazolines and aminopyrimidines as antibacterial agents. Indian J Chem. 2009;48B:1442-6.

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 2016;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, Meeran NM, 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-dimethylphenyl)-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.

Manna K, Ghosh PS, Das M, Banik U, Das A. 2-amino-3-cyanopyridin: A bioactive scaffold. IJPSR. 2014;5(6):2158-63. doi: 10.13040/IJPSR.0975-8232.5(6).2158-63.

Sabour R, Harras MF, Mohamed Al Kamaly OM, Altwaijry N. Discovery of novel 3-cyanopyridines as survivin modulators and apoptosis inducers. Molecules. 2020;25(21):4892. doi: 10.3390/molecules25214892, PMID 33105831.

Sangani HG, Bhimani KB, Khunt RC, Parikh AR. Synthesis and characterization of barbitones as antimicrobial agents. J Serb Chem Soc. 2006;71(6):587-91. doi: 10.2298/JSC0606587S.

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.

Owaba DCA, Oyeintonbara M, Oladiran RR. Chalcones as sythons for heterocyclic compounds-a review. Int J Curr Res. 2020;12(9):13672-81. doi: 10.24941/ijcr.39755.09.2020.

El-Bayouki KAM. Benzo[1,5]thiazepine: synthesis, reactions, spectroscopy, and applications. Org Chem Int. 2013;2013:1-71. doi: 10.1155/2013/210474.

Dash B, Pyrazoline hydrocyclic KS [review]. IJPSR. 2021;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.

Tiwari A, Bendi A, Bhathiwal AS. An overview on the synthesis and biological activity of chalcone-derived pyrazolines. Chemistry Select. 2021;6(45):12757-95. doi: 10.1002/slct.202103779.

Jain SK, Singhal R. A review on pyrazoline derivatives as antimicrobial agent. Int J Pharm Pharm Sci. 2020;12(6):15-24. doi: 10.22159/ijpps.2020v12i6.37456.

Kumar R, Bajia B, Srivastava YK. Synthesis and antibacterial activity of some pyrazolines using more technique. Biomed Pharmacol J. 2008;1(1):173-6. http://biomedpharmajournal.org/?p=294.

Revanasiddappa BC, Jisha MS, Kumar MV, Kumar H. Synthesis, antibacterial and antifungal evlaution of novel pyrazoline derivatives. Dhaka Univ J Pharm Sci. 2018;17(2):221-6. doi: 10.3329/dujps.v17i2.39179.

Tantawy AS, Nasr MNA, El-Sayed MAA, Tawfik SS. Synthesis and antiviral activity of new 3-methyl-1,5-diphenyl-1H-pyrazole derivatives. Med Chem Res. 2012;21(12):4139-49. doi: 10.1007/s00044-011-9960-2.

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

Zahran F, Af AA, Hamdy M. Anti-tumor activity of some pyrazoline derivatives. Biochem Lett. 2016;11(1):233-48. doi: 10.21608/blj.2016.48194.

Rahaman SA, Prasad YR, Bhuvaneswari K, Kumar P. Synthesis and antihistaminic activity of novel pyrazoline derivatives. Int J ChemTech Res. 2010;2(1):16-20.

Thach TD, Nguyen TM, Nguyen TAT, Dang CH, Luong TB, Dang VS. Synthesis and antimicrobial, antiproliferative and anti-inflammatory activities of novel 1,3,5-substituted pyrazoline sulphonamides. Arab J Chem. 2021;14(11):103408. doi: 10.1016/j.arabjc.2021.103408.

Raikar P, Shingade S. Synthesis, characterization and screening of pyrazoline derivatives for anti-inflammatory activity. IJPSR. 2018;36:2446-50. doi: 10.13040/IJPSR.0975-8232.9(6).2446-50.

Jainey PJ, Bhat IK. Antitumor, analgesic, and anti-inflammatory activities of synthesized pyrazolines. J Young Pharm. 2012;4(2):82-7. doi: 10.4103/0975-1483.96621, PMID 22754259.

Revanasiddappa B, Kumar MV, Kumar H. Synthesis and antidepressant activity of pyrazoline derivatives. Dhaka Univ J Pharm Sci. 2020;19(2):179-84. doi: 10.3329/dujps.v19i2.50634.

Liu XR, Wu H, He ZY, Ma ZQ, Feng JT, Zhang X. Design, synthesis and fungicidal activities of some novel pyrazole derivatives. Molecules. 2014;19(9):14036-51. doi: 10.3390/molecules190914036, PMID 25203055.

Matiadis D, Sagnou M. Pyrazoline hybrids as promising anticancer agents: an up-to-date overview. Int J Mol Sci. 2020;21(15):5507. doi: 10.3390/ijms21155507, PMID 32752126.

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 MN. 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 spiroheterocyclic compounds. Pharmaceutical-sciences. 2017;79(4):641-5. doi: 10.4172/pharmaceutical-sciences.1000273.