Pyrazolone Derivatives: Synthetic Chemistry, Exploring Pharmacological Activity - A Mini Review

References

1. HimlyM. Jahn-SchmidB. PittertschatscherK. BohleB. GrubmayrK. FerreiraF. EbnerH. EbnerC. IgE-mediated immediate-type hypersensitivity to the pyrazolone drug propyphenazone.J. Allergy Clin. Immunol.2003111488288810.1067/mai.2003.163 12704373
   [Google Scholar]
2. CastagnoloD. ManettiF. RadiM. BechiB. PaganoM. De LoguA. MeledduR. SaddiM. BottaM. Synthesis, biological evaluation, and SAR study of novel pyrazole analogues as inhibitors of Mycobacterium tuberculosis: Part 2. Synthesis of rigid pyrazolones.Bioorg. Med. Chem.200917155716572110.1016/j.bmc.2009.05.058 19581099
   [Google Scholar]
3. RadiM. BernardoV. BechiB. CastagnoloD. PaganoM. BottaM. Microwave-assisted organocatalytic multicomponent Knoevenagel/hetero Diels–Alder reaction for the synthesis of 2,3-dihydropyran[2,3-c]pyrazoles.Tetrahedron Lett.200950476572657510.1016/j.tetlet.2009.09.047
   [Google Scholar]
4. MoreauF. DesroyN. GenevardJ.M. VongsouthiV. GeruszV. Le FralliecG. OliveiraC. FloquetS. DenisA. EscaichS. WolfK. BusemannM. AschenbrennerA. Discovery of new Gram-negative antivirulence drugs: Structure and properties of novel E. coli WaaC inhibitors.Bioorg. Med. Chem. Lett.200818144022402610.1016/j.bmcl.2008.05.117 18571407
   [Google Scholar]
5. SauzemP.D. MachadoP. RubinM.A. da S Sant’anna, G.; Faber, H.B.; de Souza, A.H.; Mello, C.F.; Beck, P.; Burrow, R.A.; Bonacorso, H.G.; Zanatta, N.; Martins, M.A. Design and microwave-assisted synthesis of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles: novel agents with analgesic and anti-inflammatory properties.Eur. J. Med. Chem.20084361237124710.1016/j.ejmech.2007.07.018 17889969
   [Google Scholar]
6. PashaF.A. MuddassarM. NeazM.M. ChoS.J. Pharmacophore and docking-based combined in-silico study of KDR inhibitors.J. Mol. Graph. Model.2009281546110.1016/j.jmgm.2009.04.006 19447057
   [Google Scholar]
7. RosiereC.E. GrossmanM.I. An analog of histamine that stimulates recovery of tumor cells from effects of the tumor-inducing principle in crown gall.Science1951113651
   [Google Scholar]
8. BaileyD.M. HansenP.E. HlavacA.G. BaizmanE.R. PearlJ. DeFeliceA.F. FeigensonM.E. 3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants.J. Med. Chem.198528225626010.1021/jm00380a020 3968690
   [Google Scholar]
9. ShestopalovA.M. EmeliyanovaY.M. ShestopalovA.A. RodinovskayaL.A. NiazimbetovaZ.I. EvansD.H. Cross-condensation of derivatives of cyanoacetic acid and carbonyl compounds. Part 1: Single-stage synthesis of 1′-substituted 6-amino-spiro-4-(piperidine-4′)-2 H, 4 H -pyrano[2,3- c]pyrazole-5-carbonitriles.Tetrahedron200359387491749610.1016/S0040‑4020(03)01178‑5
   [Google Scholar]
10. LiuG. LiuL. JiaD. YuK. Synthesis, structure and photochromic properties of 1-phenyl-3-methyl-4-(4-bromobenzal)-pyrazolone-5 thiosemicarbazone.Struct. Chem.200516213514010.1007/s11224‑005‑2837‑6
    [Google Scholar]
11. Baciu-AtudosieL. GhinetA. BeleiD. GautretP. RigoB. BîcuE. An efficient one-pot reaction for the synthesis of pyrazolones bearing a phenothiazine unit.Tetrahedron Lett.201253456127613110.1016/j.tetlet.2012.08.152
    [Google Scholar]
12. GhorabM. El-GazzarM. AlsaidM. Synthesis, characterization and anti-breast cancer activity of new 4-aminoantipyrine-based heterocycles.Int. J. Mol. Sci.20141557539755310.3390/ijms15057539 24798749
    [Google Scholar]
13. KshatriyaR. ShelkeP. MaliS. YashwantraoG. PratapA. SahaS. Synthesis and evaluation of anticancer activity of pyrazolone appended triarylmethanes (TRAMs).ChemistrySelect20216246230623910.1002/slct.202101083
    [Google Scholar]
14. ChandrakanthaB. ShettyP. NambiyarV. IsloorN. IsloorA.M. Synthesis, characterization and biological activity of some new 1,3,4-oxadiazole bearing 2-flouro-4-methoxy phenyl moiety.Eur. J. Med. Chem.20104531206121010.1016/j.ejmech.2009.11.046 20004043
    [Google Scholar]
15. Sankappa RaiU. IsloorA.M. shetty, P.; Vijesh, A.M.; Prabhu, N.; Isloor, S.; Thiageeswaran, M.; Fun, H.K. Novel chromeno [2,3-b]-pyrimidine derivatives as potential anti-microbial agents.Eur. J. Med. Chem.20104562695269910.1016/j.ejmech.2010.02.040 20231044
    [Google Scholar]
16. IsloorA.M. KallurayaB. Sridhar PaiK. Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives.Eur. J. Med. Chem.201045282583010.1016/j.ejmech.2009.11.015 19945198
    [Google Scholar]
17. de AraújoJ.S. França da SilvaC. BatistaD.G.J. NefertitiA. FiuzaL.F.A. Fonseca-BerzalC.R. Bernardino da SilvaP. BatistaM.M. SijmM. KalejaiyeT.D. de KoningH.P. MaesL. SterkG.J. LeursR. SoeiroM.N.C. Efficacy of novel pyrazolone phosphodiesterase inhibitors in experimental mouse models of Trypanosoma cruzi.Antimicrob. Agents Chemother.2020649e00414e0042010.1128/AAC.00414‑20 32601163
    [Google Scholar]
18. SalehzadehJ. NasiriF. A facile one-pot synthesis of new functionalized pyrazolone-1,4-dithiafulvene hybrids.Mol. Divers.2024281192810.1007/s11030‑022‑10473‑x 35761142
    [Google Scholar]
19. TahirliS. AliyevaF. ŞenolH. DemukhamedovaS. AkverdievaG. AliyevaI. VeysovaS. SadeghianN. GünayS. ErdenY. TaslimiP. SujayevA. ChiragovF. Novel complex compounds of nickel with 3-(1-phenyl-2,3-dimethyl-pyrazolone-5)azopentadione-2,4: synthesis, NBO analysis, reactivity descriptors and in silico and in vitro anti-cancer and bioactivity studies.J. Biomol. Struct. Dyn.2024202412510.1080/07391102.2024.2309646 38294759
    [Google Scholar]
20. ElboshiH.A. AzzamR.A. ElgemeieG.H. JonesP.G. Crystal structure of 4-(benzo[ d]thiazol-2-yl)-1,2-dimethyl-1 H -pyrazol-3(2 H)-one.Acta Crystallogr. E Crystallogr. Commun.202480328929110.1107/S2056989024001257 38456045
    [Google Scholar]
21. AbdouM.M. GizawyM.A. Shamsel-DinH.A. Green synthesis, radioiodination and in vivo biodistribution of 5-(2-hydroxyphenyl)-2,4-dihydro-3H-pyrazol-3-one derivatives as potential candidates for lung imaging.Appl. Radiat. Isot.202420311109610.1016/j.apradiso.2023.111096 37949012
    [Google Scholar]
22. FengY. RenY. TangD. WangK.H. WangJ. HuangD. LvX. HuY. Synthesis of difluoromethylated spiropyrazolones via [3 + 2] cycloaddition of difluoroacetohydrazonoyl bromides with alkylidene pyrazolones.Org. Biomol. Chem.202422142797281210.1039/D4OB00044G 38506310
    [Google Scholar]
23. ChiuW.J. ChuT.Y. BarveI.J. SunC.M. Parallel synthesis of pyrazolone-fused cinnolines by the palladium-catalyzed [4 + 2] annulation of pyrazol-3-ones with substituted allenoates.J. Org. Chem.202489139540110.1021/acs.joc.3c02165 38133555
    [Google Scholar]
24. RegnaultR. KlupschF. El-BouazzatiH. MagnezR. Le BiannicR. Leleu-ChavainN. AhouariH. VezinH. MilletR. GoossensJ.F. ThuruX. BaillyC. Novel PD-L1-targeted phenyl-pyrazolone derivatives with antioxidant properties.Molecules2023288349110.3390/molecules28083491 37110727
    [Google Scholar]
25. AbdellattifM.H. HamedE.O. ElhoseniN.K.R. AssyM.G. EmwasA.H.M. JaremkoM. CelikI. TitiA. Kumar YadavK. ElgendyM.S. ShehabW.S. Synthesis of novel pyrazolone candidates with studying some biological activities and in-silico studies.Sci. Rep.20231311917010.1038/s41598‑023‑43575‑z 37932273
    [Google Scholar]
26. AsifM. ImranM. HusainA. Approaches for chemical synthesis and diverse pharmacological significance of pyrazolone derivatives.J. Chil. Chem. Soc.20212021210.4067/S0717‑97072021000205149
    [Google Scholar]
27. MalviyaA.R. ZalaV.K. GadhawalaZ.M. Synthesis, spectral analysis and antimicrobial activities of pyrazole and pyrazolone derivatives.Drug Chem. Sin.201675356
    [Google Scholar]
28. AceroN. BranM.F. GradillasA. OvallesA.G. LoB. LlinaresF. MunD. Synthesis and biological activity of N,N-dialkylaminoalkyl-substituted bisindolyl and diphenyl pyrazolone derivatives.Bioorg. Med. Chem.2006141916
    [Google Scholar]
29. BurjaB. Čimbora-ZovkoT. TomićS. JelušićT. KočevarM. PolancS. OsmakM. Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies.Bioorg. Med. Chem.20101872375238710.1016/j.bmc.2010.03.006 20338766
    [Google Scholar]
30. AlamF. AminR. Synthesis and pharmacological activity of some pyrazolone derivatives.202032, 4655
    [Google Scholar]
31. GolebiowskiA. TownesJ.A. LaufersweilerM.J. BrugelT.A. ClarkM.P. ClarkC.M. DjungJ.F. LaughlinS.K. SabatM.P. BooklandR.G. VanrensJ.C. DeB. HsiehL.C. JanuszM.J. WalterR.L. WebsterM.E. MekelM.J. Development of monocyclic pyrazolone based cytokine synthesis inhibitors.20051522852289
    [Google Scholar]
32. AlthagafiI. El-metwalyN.M. ElghalbanM.G. FarghalyT.A. KhedrA.M. Synthesis of pyrazolone derivatives and their nanometer ag(i) complexes and physicochemical, dna binding, antitumor, and theoretical implementations.Bioinorg. Chem. Appl.2018201811610.1155/2018/2727619
    [Google Scholar]
33. GuptaP. GuptaJ.K. Synthesis and In-vitro antifungal evaluation of 5- pyrazolones.Open Chem. J.2015371410.2174/1874842201603010017
    [Google Scholar]
34. AzimF. NadeemH. ImranM. NazS. MuhammadN. HayatA. IslamS. Characterization and biological evaluation of novel 3- methyl-5-pyrazolone derivatives.J. Med. Chem. Sci. Synth.202144252
    [Google Scholar]
35. OthmanI.M.M. Gad-ElkareemM.A.M. Hassane AnouarE. AouadiK. SnoussiM. KadriA. New substituted pyrazolones and dipyrazolotriazines as promising tyrosyl-tRNA synthetase and peroxiredoxin-5 inhibitors: Design, synthesis, molecular docking and structure-activity relationship (SAR) analysis.Bioorg. Chem.202110910470410.1016/j.bioorg.2021.104704 33609915
    [Google Scholar]
36. SaidacharyG. Veera PrasadK. DivyaD. SinghA. RameshU. SridharB. China RajuB. Convenient one-pot synthesis, anti-mycobacterial and anticancer activities of novel benzoxepinoisoxazolones and pyrazolones.Eur. J. Med. Chem.20147646046910.1016/j.ejmech.2014.02.042 24607876
    [Google Scholar]
37. KandhasamyS. RamanathanG. MuthukumarT. ThyagarajanS. UmamaheshwariN. SanthanakrishnanV.P. SivagnanamU.T. PerumalP.T. Nanofibrous matrixes with biologically active hydroxybenzophenazine pyrazolone compound for cancer theranostics.Mater. Sci. Eng. C201774708510.1016/j.msec.2017.01.001 28254336
    [Google Scholar]
38. PrajuliR. BanerjeeJ. KhanalH. Synthesis of Some Pyrazolone Derivatives and Evaluation of its Antibacterial and Cytotoxic Activity.Orient. J. Chem.20153142099210610.13005/ojc/310430
    [Google Scholar]
39. KhalilN.A. AhmedE.M. MohamedK.O. NissanY.M. ZaitoneS.A.B. Synthesis and biological evaluation of new pyrazolone–pyridazine conjugates as anti-inflammatory and analgesic agents.Bioorg. Med. Chem.20142272080208910.1016/j.bmc.2014.02.042 24631365
    [Google Scholar]
40. El SayedM.T. El-ShariefM.A.M.S. ZarieE.S. MorsyN.M. ElsheakhA.R. VoronkovA. BerishviliV. HassanG.S. Design, synthesis, anti-inflammatory activity and molecular docking of potential novel antipyrine and pyrazolone analogs as cyclooxygenase enzyme (COX) inhibitors.Bioorg. Med. Chem. Lett.201828595295710.1016/j.bmcl.2018.01.043 29426771
    [Google Scholar]
41. KimataA. NakagawaH. OhyamaR. New series of antiprion compounds : Pyrazolone derivatives have the potent activity of inhibiting protease-resistant prion protein accumulation.J. Med. Chem.200720075053505610.1021/jm070688r 17850126
    [Google Scholar]
42. QianX.K. ZhangJ. SongP.F. ZhaoY.S. MaH.Y. JinQ. WangD.D. GuanX.Q. LiS.Y. BaoX. ZouL.W. Discovery of pyrazolones as novel carboxylesterase 2 inhibitors that potently inhibit the adipogenesis in cells.Bioorg. Med. Chem.20214011618710.1016/j.bmc.2021.116187 33965840
    [Google Scholar]
43. RamajayamR. TanK.P. LiuH.G. LiangP.H. Synthesis and evaluation of pyrazolone compounds as SARS-coronavirus 3C-like protease inhibitors.Bioorg. Med. Chem.201018227849785410.1016/j.bmc.2010.09.050 20947359
    [Google Scholar]