Skip to content
2000
Volume 21, Issue 2
  • ISSN: 1573-4064
  • E-ISSN: 1875-6638

Abstract

Thiazine, a six-membered heterocycle containing nitrogen and sulfur atoms, is of paramount importance due to its diverse biological functions and broad therapeutic effects. The pharmacological attributes of 1,3-thiazine span a wide range of activities, including antileukemic, antimycobacterial, anti-inflammatory, sedative, hypnotic, anti-influenza, antituberculosis, melanogenesis inhibition, BACE1 inhibition (with anti-Alzheimer's potential), growth promotion, neuroprotective, and anticonvulsant properties. Consequently, novel synthetic methodologies and the design of new 1,3-thiazine derivatives are significantly influenced by recent research findings. This comprehensive review explores both and preclinical studies on the biomedical and therapeutic applications of 1,3-thiazine, highlighting its extensive medical relevance. It is anticipated that derivatization strategies for 1,3-thiazine will open new avenues for the development of innovative biological agents. This review aims to engage researchers, stimulating the creation of promising new treatments and preventive measures for various diseases.

Loading

Article metrics loading...

/content/journals/mc/10.2174/0115734064328915240827062052
2024-08-30
2025-06-28
Loading full text...

Full text loading...

References

  1. WangS. WangX. TuM. JiangB. TuS. Tandem one‐pot synthesis of polysubstituted 1,3‐thiazine derivatives.Chin. J. Chem.201129112411241510.1002/cjoc.201100067
    [Google Scholar]
  2. BadshahS. NaeemA. Bioactive thiazine and benzothiazine derivatives: Green synthesis methods and their medicinal importance.Molecules2016218105410.3390/molecules2108105427537865
    [Google Scholar]
  3. RiyadhM. Synthetic utility of ethylidenethiosemicarbazide: synthesis and anticancer activity of 1,3-thiazines and thiazoles with imidazole moiety.Heterocycles20138734110.3987/COM‑12‑12625
    [Google Scholar]
  4. VicentiniC.B. ForlaniG. ManfriniM. RomagnoliC. MaresD. Development of new fungicides against Magnaporthe grisea: synthesis and biological activity of pyrazolo[3,4-d][1,3]thiazine, pyrazolo[1,5-c][1,3,5]thiadiazine, and pyrazolo[3,4-d]pyrimidine derivatives.J. Agric. Food Chem.200250174839484510.1021/jf020243612166969
    [Google Scholar]
  5. AsifM. ImranM. Abida Antimicrobial activities of various thiazine based heterocyclic compounds: A mini-review.Mini Rev. Org. Chem.202219216617210.2174/1570193X18666210629102447
    [Google Scholar]
  6. AtaollahiE. SolhjooA. RezaeiZ. BehrouzM. HeidariR. shahbaziM.R. ForoozanadR. ZamaniL. KhabnadidehS. EmamiL. Novel 1,4 benzothiazine 3-one derivatives as anticonvulsant agents: Design, synthesis, biological evaluation and computational studies.Comput. Biol. Chem.202310410787010.1016/j.compbiolchem.2023.10787037099900
    [Google Scholar]
  7. TozkoparanB. AktayG. YeşiladaE. Synthesis of some 1,2,4-triazolo[3,2-b]-1,3-thiazine-7-ones with potential analgesic and antiinflammatory activities.Farmaco200257214515210.1016/S0014‑827X(01)01195‑811902657
    [Google Scholar]
  8. AbdullahiM. UzairuA. ShallangwaG.A. MamzaP.A. IbrahimM.T. Computational modelling studies of some 1,3-thiazine derivatives as anti-influenza inhibitors targeting H1N1 neuraminidase via 2D-QSAR, 3D-QSAR, molecular docking, and ADMET predictions.Beni. Suef Univ. J. Basic Appl. Sci.202211110410.1186/s43088‑022‑00280‑636000144
    [Google Scholar]
  9. KassabR.M. Al-HussainS.A. AbdelmonsefA.H. ZakiM.E.A. GomhaS.M. MuhammadZ.A. Novel xylenyl-spaced bis-thiazoles/thiazines: synthesis, biological profile as herpes simplex virus type 1 inhibitors and in silico simulations.Future Med. Chem.2024161274110.4155/fmc‑2023‑021038063202
    [Google Scholar]
  10. KoketsuM. TanakaK. TakenakaY. KwongC.D. IshiharaH. Synthesis of 1,3-thiazine derivatives and their evaluation as potential antimycobacterial agents.Eur. J. Pharm. Sci.200215330731010.1016/S0928‑0987(02)00014‑311923063
    [Google Scholar]
  11. FerreiraM. AssunçãoL.S. Filippin-MonteiroF.B. Creczynski-PasaT.B. SáM.M. Synthesis of 1,3-thiazine-2,4-diones with potential anticancer activity.Eur. J. Med. Chem.20137041141810.1016/j.ejmech.2013.10.01724177368
    [Google Scholar]
  12. El-SayedH.A. El-HashashM.M. AhmedA.E. Novel synthesis, ring transformation and anticancer activity of 1,3-thiazine, pyrimidine and triazolo[1,5-a]pyrimidine derivatives.Bull. Chem. Soc. Ethiop.20183251352210.4314/bcse.v32i3.10
    [Google Scholar]
  13. Nagendra PrasadT. EedaK.R. GudiseV.B. BashaS.F. AnwarS. Design, synthesis and biological evaluation of substituted 2-amino-1,3-thiazine derivatives as antituberculosis and anti-cancer agents.Synth. Commun.201949101277128510.1080/00397911.2019.1597125
    [Google Scholar]
  14. Gutiérrez-TarriñoS. EspinoJ. Luna-GilesF. RodríguezA.B. ParienteJ.A. Viñuelas-ZahínosE. Synthesis, characterization and antiproliferative evaluation of Pt(II) and Pd(II) complexes with a thiazine-pyridine derivative ligand.Pharmaceuticals202114539510.3390/ph1405039533921955
    [Google Scholar]
  15. NasserL.A. Abd AliA.T. ZaidA. kadhim. Synthesis, characterization of 1, 3-thiazine derivatives using chalcones, and evaluation as antimicrobial.Nat. Volatiles Essent. Oils202181396913982
    [Google Scholar]
  16. SanaK. GurdeepS. JitendraS. Molecular docking studies; 1,3 thiazines derivatives.Acta Sci. Pharm. Sci.202047121510.31080/ASPS.2020.04.0549
    [Google Scholar]
  17. CherkupallyS.R. GurralaP.R. AdkiN. AvulaS. Synthesis and biological study of novel methylene-bis-benzofuranyl-[1,5]-benzothiazepines.Org. Commun.200818494
    [Google Scholar]
  18. VinodaB.M. Synthesis of some novel 1,3-thiazine derivatives using Fe(III)- Montmorillonite catalysts as potent antimicrobial agents. Inven. Rapid Med. Chem.2016217
    [Google Scholar]
  19. HaiderF. HaiderZ. Synthesis and antimicrobial screening of some 1,3-thiazines.J. Chem. Pharm. Res.2012422632267
    [Google Scholar]
  20. DeshmukhR. Synthesis, structural study and biological evaluation of 1,3-thiazine.Der. Chem. Sin.201565963
    [Google Scholar]
  21. ThanusuJ. KanagarajanV. GopalakrishnanM. Synthesis, spectral characterization, and in vitro antibacterial and antifungal activities of novel 1,3-thiazine-2-amines comprising morpholine nucleus.J. Enzyme Inhib. Med. Chem.201025675676410.3109/1475636090338989820590407
    [Google Scholar]
  22. AbdulhusseinN.M. AboodZ.H. Synthesis, identification, and study of the biological activity of some new pyrimidine, oxazine, and thiazine derivatives through reactive chalcones.Moroccan J. Chem.202412376393
    [Google Scholar]
  23. BairamR. Murthy MuppavarapuS. ShaikA.B. KumarS. Anticonvulsant evaluation of some novel 1, 3-thiazine derivatives.Int. J. Pharm. Sci. Res.2017824772485
    [Google Scholar]
  24. BR. Murthy MS. Basha ShaikA. Design, facile synthesis, and biological evaluation of novel 1,3-thiazine derivatives as potential anticonvulsant agents.Asian J. Pharm. Clin. Res.20169527227610.22159/ajpcr.2016.v9i5.13676
    [Google Scholar]
  25. JupudiS. TalariS. KarunakaramD. GovindarajanR. Screening of in-vitro anti-inflammatory activity of some newly synthesized 1, 3-thiazine derivatives.Int. J. Res. Pharm. Chem.20133213220
    [Google Scholar]
  26. FuL. YeD. LiY. YinS. Synthesis and calming activity of 6H-2-Amino-4-Aryl-6-(4-β-D-Allopyranosyloxyphenyl)-1,3-Thiazine.Chem. Nat. Compd.201046216917210.1007/s10600‑010‑9559‑8
    [Google Scholar]
  27. KaiH. MoriokaY. TomidaM. TakahashiT. HattoriM. HanasakiK. KoikeK. ChibaH. ShinoharaS. KanemasaT. IwamotoY. TakahashiK. YamaguchiY. BabaT. YoshikawaT. TakenakaH. 2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 2: Orally bioavailable compounds.Bioorg. Med. Chem. Lett.200717143925392910.1016/j.bmcl.2007.04.09917531479
    [Google Scholar]
  28. LiW. XiaL. HuA. LiuA. PengJ. TanW. Design and synthesis of 4‐ A lkyl‐2‐amino(acetamino)‐6‐aryl‐1,3‐thiazine derivatives as influenza neuraminidase inhibitors.Arch. Pharm.2013346963564410.1002/ardp.20130012223926081
    [Google Scholar]
  29. AbdallaM. GomhaS. Abd El-AzizM. SeragN. Synthesis and evaluation of some novel thiazoles and 1,3-thiazines as potent agents against the rabies virus.Turk. J. Chem.20164044145310.3906/kim‑1506‑13
    [Google Scholar]
  30. HaS.K. KoketsuM. LeeM. MoonE. KimS.H. YoonT.J. KimS.Y. Inhibitory effects of 1,3-thiazine derivatives on melanogenesis.J. Pharm. Pharmacol.201061121657166310.1211/jpp.61.12.001119958589
    [Google Scholar]
  31. KoriyamaY. HoriA. ItoH. YonezawaS. BabaY. TanimotoN. UenoT. YamamotoS. YamamotoT. AsadaN. MorimotoK. EinaruS. SakaiK. KanazuT. MatsudaA. YamaguchiY. OgumaT. TimmersM. TritsmansL. KusakabeK. KatoA. SakaguchiG. Discovery of Atabecestat (JNJ-54861911): A thiazine-based β-amyloid precursor protein cleaving enzyme 1 inhibitor advanced to the phase 2b/3 early clinical trial.J. Med. Chem.20216441873188810.1021/acs.jmedchem.0c0191733588527
    [Google Scholar]
  32. HushareV.J. RajputP.R. GhodileN.G. MalpaniM.O. Synthesis, characterization of some novel heterocycles and their growth promoting effect on some flowering plants.Int. J. Pharm. Tech. Res.20135420425
    [Google Scholar]
  33. LiY. KongS. YangF. XuW. Protective effects of 2-amino-5,6-dihydro-4h-1,3-thiazine and its derivative against radiation-induced hematopoietic and intestinal injury in mice.Int. J. Mol. Sci.2018195153010.3390/ijms1905153029883417
    [Google Scholar]
  34. BlokhinaS.V. VolkovaT.V. Ol’khovichM.V. SharapovaA.V. ProshinA.N. BachurinS.O. PerlovichG.L. Synthesis, biological activity, distribution and membrane permeability of novel spiro-thiazines as potent neuroprotectors.Eur. J. Med. Chem.20147781710.1016/j.ejmech.2014.02.05224607585
    [Google Scholar]
  35. Torres-GarcíaP. Viñuelas-ZahínosE. Luna-GilesF. EspinoJ. Barros-GarcíaF.J. Zinc(II) complexes with novel 1,3-thiazine/pyrazole derivative ligands: Synthesis, structural characterization and effect of coordination on the phagocytic activity of human neutrophils.Polyhedron201130152627263610.1016/j.poly.2011.07.014
    [Google Scholar]
  36. LevtsovaA.A. ChupakhinV.I. ProshinA.N. PushinA.N. TrofimovaT.P. ZefirovaO.N. Design of potential NO-synthase inhibitors on the basis of 2-amino-5,6-dihydro-4H-1,3-thiazine derivatives.Moscow Univ. Chem. Bull.200762524324510.3103/S0027131407050033
    [Google Scholar]
  37. BadreyM.G. GomhaS.M. AbdelmonsefA.H. El-ReedyA.A.M. Syntheses and molecular docking analysis of some new thiazole and thiazine derivatives as three armed molecules with a triazine ring as a core component: A search for anti-obesity agents.Polycycl. Aromat. Compd.202444127529310.1080/10406638.2023.2173617
    [Google Scholar]
/content/journals/mc/10.2174/0115734064328915240827062052
Loading
/content/journals/mc/10.2174/0115734064328915240827062052
Loading

Data & Media loading...

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test