Synthesis of some new 1,3,5-trisubstituted pyrazoles as antioxidant and antiinflammatory agents

  • Pragi Arora Research Scholar, IKG Punjab Technical University, Kapurthala, 144603 (Punjab)
  • Jagdeep Dua Associate Professor, Shivalik College of Pharmacy, Nangal, 140124 (Punjab)
  • Jitender Singh Professor, Lord Shiva College of Pharmacy, Sirsa, 125055 (Haryana)

Abstract

A series of some new 1,3,5-trisubstituted pyrazoles was synthesized by the reaction of α-β dibromochalcones with phenylhydrazine hydrochloride. α-β-Dibromochalcones were prepared by the regioselective bromination of respective chalcones with tetrabutylammonium tribromide. The synthesized trisubstituted pyrazoles were evaluated for their anti-inflammatory and antioxidant properties.


Keywords: α-β-Dibromochalcones, 1,3,5-Trisubstituted pyrazoles, Tetrabutylammonium tribromide, Anti-inflammatory and antioxidant activities

Downloads

Download data is not yet available.

Author Biographies

Pragi Arora, Research Scholar, IKG Punjab Technical University, Kapurthala, 144603 (Punjab)

Research Scholar, IKG Punjab Technical University, Kapurthala, 144603 (Punjab)

Jagdeep Dua, Associate Professor, Shivalik College of Pharmacy, Nangal, 140124 (Punjab)

Associate Professor, Shivalik College of Pharmacy, Nangal, 140124 (Punjab)

Jitender Singh, Professor, Lord Shiva College of Pharmacy, Sirsa, 125055 (Haryana)

Professor, Lord Shiva College of Pharmacy, Sirsa, 125055 (Haryana)

References

1. Micetich R G & Rastogi R B.; Can CA 1730808 (Cl Co7DL31/12).; Synthesis of Pyrazole and Isoxazole in Triethanolamine Medium. Chem Abstr, 1982; 98:1983, 72087.
2. Khalid K.; Smaail R.; Youssef R.; Jamal T.; M’hammed A., Synthesis and Pharmacological Activities of Pyrazole Derivatives:A Review., Molecules, 2018; 23:134
3. Seyed Nasser.;Ostad, A. S., Synthesis and Anticancer Activity of 1, 3, 5-Triaryl-1H-Pyrazole.,Letters in Drug Design & Discovery, 2015; 12(999):1-1.
4. Mohd J. Naim.; Ozair A.; Farah N.; Md. Jahangir A.; and Perwaiz,A., Current status of pyrazole and its biological activities., J Pharm Bioallied Sci. 2016;Jan-Mar, 8(1):2–17.
5. Bedia K-K.; Hale Z. T.; Serkan I˙Kiz.; A. Funda B.; Sevim R.; N.Yakut O. & Seyyal AK., Synthesis and antinociceptive-antimicrobial activities of some new amide derivatives of 3,5-di/-and 1,3,5-trimethylpyrazoles., Journal of Enzyme Inhibition and Medicinal Chemistry, August 2008; 23(4):454–461
6. Magda M. F. I.; Nagy M. Khalifa., Hoda H. F.; Hend M. EL-S.; Eman, S.N., Anticancer evaluation of novel 1,3,4-trisubstituted pyrazole candidates bearing different nitrogenous heterocyclic Moieties., Biomedical Research.;2016; 27(4):1087-1093
7. Mukherjee A.; Sarkar A.; Pyrazole-based P,N-ligand for palladium catalyst: applications in Suzuki coupling and amination reactions; Arkivoc.; 2003; 9:87
8. Sanz D.; Jimenez J. A.; Claramunt R. M.; Elguero, Multidentate Ligands from N-hydroxy and N-methyl Pyrazole J. Arkivoc, 2004; 4:100
9. Kobayashi T.; Uchiyama Y.; Neighboring effect of pyrazole rings: regio- and stereoselective Wagner–Meerwein rearrangement in electrophilic addition reactions of norbornadiene-fused pyrazoles.; J. Chem. Soc., 2000; 2731
10. Novinson, T.; Robins, R. K.; Matthews, T. R.; Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors:  Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide.; J. Med. Chem., 1997; 40(9):1347-1365
11. David F. Farrell., Chalcone derivatives as precursors of 1,2,3,4 tetrahydoquinolones.,Tetrahedron. 1990; 46(3):885-894
12. Litkei D; Khilya VP; A. L. Tokesh; Antush; A. V. Turo.; Reaction of chalcones with N-bromosuccinimide.,Chemistry of Heterocyclic Compounds.;1995; 31(4):432–440
13. Khurana J.M., Maikap G. C.; Sahoo P. K.; Stereoselective Debromination of vic-Dibromides to E-Alkenes with Dimethylformamide., Synthesis, 1991; 10:827-828.
14. Vijayshree N.; Samuelson A. G.; Selective debromination of activated vicinal dibromides by copper promoted by copper (II); Tetrahedron Lett., 1992, 33 (4):559-560.
15. Ranu B. C.; Jana R. Catalysis by Ionic Liquid; A Green Protocol for the Stereoselective Debromination of vicinal-Dibromides by [pmIm] BF4 under Microwave Irradiation; J. Org. Chem., 2005; 70 (21):8621-8624.
16. Donnely J.A and Higginbotham C.L; Flavone formation in the wheeler Aurone Synthesis; Tetrahedron.; 1990; 46:7219.
17. Shoji K; Takaaki K; Tsuyoshi O; Shizuo F; Synthesis of Bromoacetyl Derivatives by use of tetrabutylammonium tribromide; Bull. Chem. Soc. Jpn.; 1987; 60:1159-1160
18. Berthelot J; Benammar Y; Desmazieres, B.; Action of tetrabutylammonium tribromide with para-substituted chalcones in protic and aprotic media; Can. J. Chem.; 1995; 73:1526-1530.
Statistics
4 Views | 4 Downloads
How to Cite
Arora, P., Dua, J., & Singh, J. (2019). Synthesis of some new 1,3,5-trisubstituted pyrazoles as antioxidant and antiinflammatory agents. Journal of Drug Delivery and Therapeutics, 9(2-s), 343-347. https://doi.org/10.22270/jddt.v9i2-s.2722