Synthesis characterization and Preliminary Pharmacological Evaluation of new 2-pyrazoline derivatives derived from resorcinol

Main Article Content

Mervat Mohammed K.
Tagreed N-A. Omar

Keywords

Pharmacological, derivatives, Synthesis, antioxidant

Abstract

Chalcones were used to create a number of 2-pyrazoline derivatives, which were then tested for their pharmacological effects.
Claisen-Schmidt prepared the chalcones (1–5). Acetophenone was used as the condensing agent in a reaction with several para-substituted benzaldehydes while KOH was present. The reaction was monitored by TLC, and the resultant intermediates were examined by melting point and FT-IR.
Various In a single pot, chalcones (1–5) and Hydrazine monohydrate were reacted with glacial acetic acid at a temperature of 50 °C for roughly 24 hours to produce 2-pyrazoline derivatives. The antioxidant chemical (guaiacol) was added after pyrazoline II (1–5) was produced, and the reaction was then watched by TLC to make sure it was finished. The mixture was chilled until crystal formation was complete in an ice-water bath. the 2-pyrazoline derivatives a1, b1, c1, d1, and e1 by adding them to crushed ice, storing them in the refrigerator for the next day, filtering, recrystallizing, and drying them. Based on their spectral data, the structures of the recently synthesized 2-pyrazoline derivatives have been established. The synthetic compounds were tested for their anti-inflammatory and antibacterial properties.

Abstract 214 | PDF Downloads 164

References

1. Heterocyclic Compound: Introduction, Classification and Applications of Heterocyclic Compound [Internet]. [cited 2022 Sep 8]. /
2. Kaur N. Miscellaneous use of Raney nickel for the synthesis of heterocycles. Raney Nickel-Assisted Synth Heterocycles. 2022 Jan 1;159–210.
3. Matiadis D, Sagnou M. Pyrazoline hybrids as promising anticancer agents: An up-to-date overview. Int J Mol Sci. 2020;21(15):1–41.
4. Najmuldeen ZD, Omar TNA. Synthesis and Evaluation of New Pyrazoline derivatives containing Sulfonamide Moiety as Anti-microbial and. :1–10.
5. JAIN SK, SINGHAL R. a Review on Pyrazoline Derivatives As Antimicrobial Agent. Int J Pharm Pharm Sci. 2020;12(6):15–24.
6. Hegde H, Ahn C, Shwetha D, Gaonkar SL, Shetty NS. Synthesis of new pyrazoline derivatives and its antimicrobial and antioxidant activities. J Korean Chem Soc. 2017;61(5):291–5.
7. Jasril J, Ikhtiarudin I, Hasti S, Reza AI, Frimayanti N. Microwave-assisted synthesis, in silico studies and in vivo evaluation for the antidiabetic activity of new brominated pyrazoline analogs. Thai J Pharm Sci. 2019;43(2):83–9.
8. 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):133–9.
9. Gatphoh BFD, Aggarwal NN, Madan Kumar S, Vijay Kumar M, Revanasiddappa BC. Synthesis, in silico analysis and antidepressant activity of 1,3,4-oxadiazole derivatives. Bangladesh J Pharmacol. 2022;17(1):14–21.
10. Doan TN, Tran DT. Synthesis, Antioxidant and Antimicrobial Activities of a Novel Series of Chalcones, Pyrazolic Chalcones, and Allylic Chalcones. Pharmacol Pharm [Internet]. 2011 Oct 19 [cited 2022 Jun 20];02(04):282–8.
11. Anwar C, Prasetyo YD, Matsjeh S, Haryadi W, Sholikhah EN, Nendrowati. Synthesis of chalcone derivatives and their in vitro anticancer test against breast (T47D) and colon (wiDr) cancer cell line. Indones J Chem. 2018;18(1):102–7.
12. Rammohan A, Bhaskar BV, Venkateswarlu N, Gu W, Zyryanov G V. Design, synthesis, docking and biological evaluation of chalcones as promising antidiabetic agents. Bioorg Chem [Internet]. 2020;95:103527.
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):858–68.
14. Emam SH, Sonousi A, Osman EO, Hwang D, Kim G Do, Hassan RA. Design and synthesis of methoxyphenyl- and coumarin-based chalcone derivatives as anti-inflammatory agents by inhibition of NO production and down-regulation of NF-κB in LPS-induced RAW264.7 macrophage cells. Bioorg Chem. 2021 Feb 1;107:104630.
15. Bouthenet E, Oh KB, Park S, Nagi NK, Lee HS, Matthews SE. Synthesis and antimicrobial activity of brominated resorcinol dimers. Bioorganic Med Chem Lett [Internet]. 2011;21(23):7142–5.
16. Hiasa M, Kurokawa M, Ohta K, Esumi T, Akita H, Niki K, et al. Identification and purification of resorcinol, an antioxidant specific to Awa-ban (pickled and anaerobically fermented) tea. Food Res Int. 2013;54(1):72–80.
17. H. Naser N, F. Mahdi M, N-A Omar T, A. Fadhil A. Synthesis and Preliminary Pharmacological Evaluation of New Analogues of Diclofenac as Potential Anti-inflammatory Agents. Iraqi J Pharm Sci ( P-ISSN 1683 - 3597 E-ISSN 2521 - 3512). 2017;20(1):25–32.