Synthesis, Characterization, Anti-Inflammatory, and Antimicrobial Evaluation of New 2-Pyrazolines Derivatives Derived from Guaiacol

Authors

  • Mervat Mohammed K Ministry of Health and Environment, Department of Health in Diyala, Diyala , Iraq
  • Tagreed N-A Omar Department of Pharmaceutical Chemistry, College of Pharmacy,. University of Baghdad, Baghdad, Iraq

DOI:

https://doi.org/10.31351/vol32issSuppl.pp254-261

Keywords:

Pyrazoline, one pot reaction, Chalcones, guaiacol, antimicrobial activity.

Abstract

Abstract:

        Chalcones were used to synthesis series of 2-pyrazoline derivatives and evaluated their antimicrobial and anti-inflammatory activities

       (E)-1,3-diphenylprop-2-en-1-one (1-5) were synthesized by Claisen-Schmidt Condensation method through the reaction of acetophenone with five various para substituted benzaldehyde in presence of KOH, the reaction monitoring by TLC and the result intermediates were checked by melting point and FT-IR

Various 2-Pyrazoline derivatives were prepared by one pot reaction that involved the refluxing of (E)-1,3-diphenylprop-2-en-1-one (1–5) and Hydrazine monohydrate in the presence of glacial acetic acid for 24 hours at a temperature of (45–50) °C for a duration 24 hrs. pyrazoline II (1-5) was formed, then antioxidant compound (guaiacol) was added reflex for 24-48 hours, monitoring by TLC to ensure the reaction was completed. The final mixture was cooled in ice-water bathe until the formation of crystals were completed, added to crushed ice, kept in refrigerator overnight, filter, recrystallized and then dried to get 2-pyrazoline derivatives, IIIa, IIIb, IIIc, IIId and, IIIe. based on the spectral data 2-pyrazoline derivatives structures have been confirmed. The synthesized compounds were screened for their antimicrobial activity and anti-inflammatory.

How to Cite

1.
Mervat Mohammed K, Tagreed N-A Omar. Synthesis, Characterization, Anti-Inflammatory, and Antimicrobial Evaluation of New 2-Pyrazolines Derivatives Derived from Guaiacol . Iraqi Journal of Pharmaceutical Sciences [Internet]. 2023 Nov. 4 [cited 2024 Dec. 22];32(Suppl.):254-61. Available from: https://bijps.uobaghdad.edu.iq/index.php/bijps/article/view/2688

Publication Dates

References

Younus ZG, Omar TN. Synthesis, Characterization and Evaluation of Antioxidant Activity of New Pyrazolines Derivatives. J Res Med Dent Sci. 2023;11(01): 082-089.

Salum KA, Alidmat MM, Khairulddean M, et al. Design, synthesis, characterization, and cytotoxicity activity evaluation of mono-chalcones and new pyrazolines derivatives. J Appl Pharm Sci. 2020;10(8):20–36.

Jang S, Jung JC, Oh S. Synthesis of 1,3-diphenyl-2-propen-1-one derivatives and evaluation of their biological activities. Bioorganic Med Chem. 2007;15(12): 4098-4105.

Kumari S, Paliwal SK, Chauhan R. An Improved Protocol for the Synthesis of Chalcones Containing Pyrazole with Potential Antimicrobial and Antioxidant Activity. Curr Bioact Compd. 2018;14(1):39–47.

VásquezYA, Osorio ME, San Martín DA, et al. Antimicrobial,anti-inflammatory and anti-oxidant activities of polyoxygenated chalcones. J Braz Chem Soc. 2019;30(2):286–304.

Nasir Abbas ,Bukhari S, Jasamai M, et al. Review of Methods and Various Catalysts Used for Chalcone Synthesis. Mini Rev Org Chem. 2013;10(1):73–83.

Jain S, Kumar S, Lamba BY, Patra J, Mahindroo N. Nanocatalysts: Applications in synthesis of chalcones–a review. Synth Commun. 2021;51(1):1–12.

Pierigé M, Iuliano A, Angelici G, Casotti G. Stabilized Arylzinc Iodides in Negishi Acylative Cross-Coupling: A Modular Synthesis of Chalcones. Organics. 2022 Apr 23;3(2):87–94.

Rahim MA, Bhuiayan MMH, Matin MM. Microwave Assisted Efficient Synthesis of Some Flavones for Antimicrobial and ADMET Studies. J Sci Res. 2020;12(4): 673-685.

Singh G, Goyal A, Bhatti RS, Arora S. Pyrazoline as a medicinal scaffold. Bionatura. 2019; 4(4).2-6.

M.T. Albuquerque HMMS. Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles. Curr Org Chem. 2014;18(26): 2750 - 2775.

Najmuldeen ZD, Omar TNA. Synthesis and Evaluation of New Pyrazoline derivatives containing Sulfonamide Moiety as Anti-microbial and Anti-inflammatory Agents. J Res Med Dent Sci. 2023;11(01):1–10.

Al-Nakeeb MR, Omar TNA. Synthesis, characterization and preliminary study of the anti-inflammatory activity of new pyrazoline containing ibuprofen derivatives. Iraqi J Pharm Sci. 2019;28(1): 133-139.

JAIN SK, SINGHAL R. a Review on Pyrazoline Derivatives As Antimicrobial Agent. Int J Pharm Pharm Sci. 2020;12(6):15–24.

Farooq S, Ngaini Z. One-pot and two-pot methods for chalcone derived pyrimidines synthesis and applications. J Heterocycl Chem. 2021;58(6): 1209-1224.

Farooq S, Ngaini Z, Mortadza NA. Microwave-assisted Synthesis and Molecular Docking Study of Heteroaromatic Chalcone Derivatives as Potential Antibacterial Agents. Bull Korean Chem Soc. 2020;41(9):918–924.

Gao T, Zhang Y, Shi J, Mohamed SR et al. The Antioxidant Guaiacol Exerts Fungicidal Activity Against Fungal Growth and Deoxynivalenol Production in Fusarium graminearum. Front Microbiol. 2021;12(762844):1–10.

Li N, Su J, Wang H, Cavaco-Paulo A. Production of antimicrobial powders of guaiacol oligomers by a laccase-catalyzed synthesis reaction. Process Biochem. 2021 1;111:213–20.

Helio M.T, Clementina M.M. Santos JASC et al. Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles. Current Organic Chemistry. 2014;18(26). 2750 - 2775

Walsh DJ, Livinghouse T, Goeres DM, Mettler M, et al. Antimicrobial Activity of Naturally Occurring Phenols and Derivatives Against Biofilm and Planktonic Bacteria. Front Chem. 2019;7(10):1-13

Mohammed ZB, Omar TN. Chemical Design, Synthesis And Biological Evaluoation Of Mutual Prodrug Of Gabapentin With Different Types Of Phenolic And Alcoholic Antioxidants. Syst Rev Pharm. 2021;12(1):858–868.

Kannan, Shaymaa, Omar TN. Synthesis and Preliminary Pharmacological Evaluation of New Pyrazoline Derive from Different Heterocyclic Aldehydes. J Popul Ther Clin Pharmacol. 2023;30(14):311–318.

Baluja S, Chanda S, Bhalodia R, Talaviya R. Synthesis, characterization and in vitro study of antibacterial, antifungal activities of some novel dihydropyrimidinthione derivatives. Lat Am Appl Res. 2014;44(4):289–293.

Abbas SS, Kubba AMA. Synthesis, characterization and preliminary antimicrobial evaluation with DFT Study of new thiazole derivatives. Iraqi J Pharm Sci. 2018;27(1):69–78.

Mohammed Kamil H. Nedaa A Hameed. Nedaa A.Hameed. Synthesis, Characterization and Preliminary Antimicrobial Evaluation of New Schiff bases and Aminothiadiazole Derivatives of N- Substituted Phthalimide Research J. Pharm. and Tech 2022; 15(9):3861-3865.

Arikan S. Current status of antifungal susceptibility testing methods. Med Mycol. 2007;45(7):569–587.

Mohammed W, Yaqeen, Omer N-A, Tagreed. Design, Synthesis and Antibacterial Evaluoation of mutual Prodrugs of Antioxidants with Different Quinolone Antibiotics. Biochem Cell Arch. 2021;21(1):1759–1768.

N A . Omar T. Synthesis and Preliminary Pharmacological Evaluation of Esters and Amides Derivatives of Naproxen as Potential Anti-Inflammatory Agents. Iraqi J Pharm Sci. 2017;22(1):120–127.

H. Naser N, F. Mahdi M, N-A Omar T,et al. Synthesis and Preliminary Pharmacological Evaluation of New Analogues of Diclofenac as Potential Anti-inflammatory Agents. Iraqi J Pharm Sci. 2017;20(1):25–32.

Veerasamy R, Roy A, Karunakaran R, Rajak H. Structure–activity relationship analysis of benzimidazoles as emerging anti-inflammatory agents: An overview. Pharmaceuticals. 2021; 14(7).2-31.

Kolli M. Mechanism of antimicrobial activity and antioxidant activities of the essential oil and the methanolic extract of carum montanum from Algeria. Ann Agric Sci Moshtohor. 2018;56(1):253–62.

Raauf AMR,Omar TNA,Mahdi MF. Synthesis, molecular docking and anti-inflammatory evaluation of new trisubstituted pyrazoline derivatives bearing benzenesulfonamide moiety. Nat Prod Res. 2022;20(1):21.

Omar TN. Synthesis of anti-inflammatory aromatic Schiff bases Synthesis of Schiff Bases of Benzaldehyde and Salicylaldehyde as Anti-inflammatory Agents. Iraqi J Pharm Sci. 2007; 16(2):5–11.

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Published

2023-11-04