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2000
Volume 21, Issue 6
  • ISSN: 1573-4072
  • E-ISSN: 1875-6646

Abstract

Introduction

As per the literature survey, the pyrimidine-based molecules display prominent antibacterial, anti-inflammatory, antioxidant, anticancer, analgesic, anticonvulsant, anti-tubercular and antimalarial properties. The biological relevance of pyrimidine-based pharmacophore structures encourages us to synthesize some novel imines derived from 2-amino pyrimidine and substituted benzaldehydes.

Objective

The present communication describes the synthesis of six imines derived from 2-aminopyrimidine. The tri-potassium phosphate catalyst used in the current study optimizes the microwave-assisted synthesis of these novel Schiff bases. The reported method for the synthesis of imines is found to be eco-friendly in terms of the effective use of catalyst AlO-KPO with microwave in the synthesis of pyrimidine-based Schiff bases.

Methods

Different spectroscopic methods, such as 1H NMR, IR, GCMS and elemental analysis, were used to determine the structure of all synthesized Schiff bases. Further, the imines were screened for antibacterial properties to check their inhibitory potency against and .

Results

The biological potency of imines was also studied for their antioxidant and anti-inflammatory activity. The obtained results reveal that Schiff base showed potent anti-inflammatory activity with a 31.538% ± 2.055 inhibition of inflammation. Moreover, the synthesized imines have been screened and studied for their antioxidant activity by DPPH and nitric oxide radical scavengers. Some of these, like show potency to scavenge DPPH radicals as compared to standard. In the antimicrobial investigation, most of the Schiff bases showed good inhibitory activity against various tested pathogens. The current study, therefore, contributes to investigate a new class of imines with structurally modified anti-inflammatory and antioxidant drugs.

Conclusion

The outcome of the study revealed that compound showed promising anti-inflammatory activity with inhibition of inflammation. All imines display antibacterial potency in compounds , , and . The antibacterial properties of these imines are attributed to - and as primary bioactive substituents present in the moiety of imines, which enhance inhibitory properties against tested pathogens. The antioxidant scavenging activity of imines indicates that compounds and represent better anti-oxidants as DPPH scavengers than standard ascorbic acid.

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2025-10-30
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References

  1. MehtaP.D. SengarN.P.S. PathakA.K. 2-Azetidinone: A new profile of various pharmacological activities.Eur. J. Med. Chem.201045125541556010.1016/j.ejmech.2010.09.035 20970895
    [Google Scholar]
  2. BrandiA. CicchiS. CorderoF.M. Novel syntheses of azetidines and azetidinones.Chem. Rev.200810893988403510.1021/cr800325e 18781723
    [Google Scholar]
  3. BaghelB.G.Y. PandhurnekarH. BhattacharyaD. PandhurnekarC. A brief review on thiazolidinones and azetidinones: Synthesis and biological activities.JASR202120212536
    [Google Scholar]
  4. MukerjeeD.D. ShuklaS.K. ChowdharyB.L. Synthesis of some new formazans as potential antiviral agents.Arch. Pharm.19813141299199410.1002/ardp.19813141204 7325793
    [Google Scholar]
  5. GodhaniD.R. MehtaU.P. SaiyadA.H. ParmarK.P. MehtaJ.P. The “Design, synthesis, characterization and biological evaluation of some Azetidinone derivatives containing pyrimidine moiety”.Indian J. Chem.202362111193120010.56042/ijc.v62i11.4825
    [Google Scholar]
  6. KumarR. SinghA.A. KumarU. JainP. SharmaA.K. KantC. Haque FaiziM.S. Recent advances in synthesis of heterocyclic Schiff base transition metal complexes and their antimicrobial activities especially antibacterial and antifungal.J. Mol. Struct.20231294213634610.1016/j.molstruc.2023.136346
    [Google Scholar]
  7. MalikM.A. DarO.A. GullP. WaniM.Y. HashmiA.A. Heterocyclic Schiff base transition metal complexes in antimicrobial and anticancer chemotherapy.MedChemComm20189340943610.1039/C7MD00526A 30108933
    [Google Scholar]
  8. KumarS. NarasimhanB. Therapeutic potential of heterocyclic pyrimidine scaffolds.Chem. Cent. J.20181213810.1186/s13065‑018‑0406‑5 29619583
    [Google Scholar]
  9. AshourH.M. ShaabanO.G. RizkO.H. El-AshmawyI.M. Synthesis and biological evaluation of thieno [2′,3′:4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidines as anti-inflammatory and analgesic agents.Eur. J. Med. Chem.20136234135110.1016/j.ejmech.2012.12.003 23376247
    [Google Scholar]
  10. TozkoparanB. ErtanM. KelicenP. DemirdamarR. Synthesis and anti-inflammatory activities of some thiazolo[3,2-a]pyrimidine derivatives.Farmaco199954958859310.1016/S0014‑827X(99)00068‑3 10555260
    [Google Scholar]
  11. MeneghessoS. VanderlindenE. StevaertA. McGuiganC. BalzariniJ. NaesensL. Synthesis and biological evaluation of pyrimidine nucleoside monophosphate prodrugs targeted against influenza virus.Antiviral Res.2012941354310.1016/j.antiviral.2012.01.007 22306172
    [Google Scholar]
  12. ElattarK.M. MertB.D. MonierM. El-MekabatyA. Advances in the chemical and biological diversity of heterocyclic systems incorporating pyrimido[1,6-a]pyrimidine and pyrimido[1,6-c]pyrimid] ine scaffolds.RSC Advances20201026154611549210.1039/D0RA00411A 35558641
    [Google Scholar]
  13. KumarS. LimS.M. RamasamyK. VasudevanM. ShahS.A.A. SelvarajM. NarasimhanB. Synthesis, molecular docking and biological evaluation of bis-pyrimidine Schiff base derivatives.Chem. Cent. J.20171118910.1186/s13065‑017‑0322‑0 29086867
    [Google Scholar]
  14. KaurA. SharmaS. VermaD. SahniT. KaurS. Synthesis, characterization and fungicidal activity of novel 2-aminopyrimidine Schiff bases.Indian J. Chem.2023621424810.56042/ijc.v62i1.70390
    [Google Scholar]
  15. KajalA. BalaS. KambojS. SharmaN. SainiV. Schiff Bases: A versatile pharmacophore.J. Catal.2013201389351210.1155/2013/893512
    [Google Scholar]
  16. KaleV. BhopalkarG. Optimization of pyridine based Schiff bases: Design, synthesis and determination of anti-inflammatory, antioxidant and antimicrobial activity.Current Chemistry Letters20241319110010.5267/j.ccl.2023.8.006
    [Google Scholar]
  17. PadmanabhanP. JangleS.N. Evaluation of in-vitro anti-inflammatory activity of herbal preparation, a combination of four medicinal plants.Int. J. Appl. Basic Med.20122109116
    [Google Scholar]
  18. EliasG. RaoM.N. Inhibition of albumin denaturation and antiinflammatory activity of dehydrozingerone and its analogs.Indian J. Exp. Biol.1988267540542 3198157
    [Google Scholar]
  19. LeeH.S. Antioxidative activity of browning reaction product isolated from storage-aged orange juice.J. Agric. Food Chem.199240455055210.1021/jf00016a004
    [Google Scholar]
  20. ChakraborthyG.S. Free radical scavenging activity of Costus speciosus leaves.Indian J. Pharm. Educ. Res2009439698
    [Google Scholar]
  21. AbbassE.M. KhalilA.K. El-NaggarA.M. Eco‐friendly synthesis of novel pyrimidine derivatives as potential anticancer agents.J. Heterocycl. Chem.20205731154116410.1002/jhet.3852
    [Google Scholar]
  22. MobinikhalediA. SteelP.J. PolsonM. Rapid and efficient synthesis of schiff bases catalyzed by copper nitrate.Synth. React. Inorg. Met.-Org. Nano-Met. Chem.200939418919210.1080/15533170902858047
    [Google Scholar]
  23. ŞendilK. TekinT. GöksuH. OğuzM. AnılB. GültekinM.S. A novel method for the synthesis of newfangled asymmetric Schiff bases from α‐amino acids under ultrasonic conditions and in aqueous medium.J. Chin. Chem. Soc.201663980881710.1002/jccs.201600094
    [Google Scholar]
  24. SachdevaH. SarojR. KhaturiaS. DwivediD. Operationally simple green synthesis of some Schiff bases using grinding chemistry technique and evaluation of antimicrobial activities.Green Process. Synth.20121546947710.1515/gps‑2012‑0043
    [Google Scholar]
  25. GüngörT. Preparation of novel imidazo[1,2-a]pyrimidine derived schiff bases at conventional and microwave heating conditions.Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi202022242843810.25092/baunfbed.707673
    [Google Scholar]
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