Skip to content
2000
  1. Home
  2. A-Z Publications
  3. Current Organic Chemistry
  4. Volume 28, Issue 20
  5. Article
Volume 28, Issue 20
  • ISSN: 1385-2728
  • E-ISSN: 1875-5348

Abstract

We have created novel 1,2,3-triazole-based benzothiazinone derivatives in the current work. The produced compounds' antioxidant, antifungal, and antitubercular properties were assessed. Moreover, a simulated molecular docking analysis was conducted on the cytochrome P450 lanosterol 14α-demethylase active site to elucidate the enzyme's binding affinity and interactions with synthesised benzothiazinone derivatives. A notable correlation between these compounds' antifungal activity and binding score was indicated by molecular docking data. The synthetic 1,2,3-triazole-based benzothiazinone derivatives may satisfy the structural criteria for creating novel antifungal drugs, according to the results of the and investigations.

© 2024 Bentham Science Publishers
Loading

Article metrics loading...

/content/journals/coc/10.2174/0113852728316869240626060258
2024-12-01
2025-01-10

  • From This Site

    /content/journals/coc/10.2174/0113852728316869240626060258
    dcterms_title,dcterms_subject,pub_keyword
    -contentType:Contributor -contentType:Concept -contentType:Institution
    10
    5
Loading full text...

Full text loading...

References

  1. KeriR.S. PatilM.R. PatilS.A. BudagumpiS. A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry.Eur. J. Med. Chem.20158920725110.1016/j.ejmech.2014.10.059 25462241
     [Google Scholar]
  2. SabatiniS. GosettoF. SerritellaS. ManfroniG. TabarriniO. IraciN. BrincatJ.P. CarosatiE. VillariniM. KaatzG.W. CecchettiV. Pyrazolo[4,3-c][1,2]benzothiazines 5,5-dioxide: A promising new class of Staphylococcus aureus NorA efflux pump inhibitors.J. Med. Chem.20125573568357210.1021/jm201446h 22432682
     [Google Scholar]
  3. ArmeniseD. TrapaniG. ArrivoV. LaraspataE. MorlacchiF. Research on potentially bioactive aza and thiaza polycyclic compounds containing a bridgehead nitrogen atom. III. Synthesis and antimicrobial activity of some 1,4‐benzothiazines and pyrrolobenzothiazines.J. Heterocycl. Chem.20003761611161610.1002/jhet.5570370634
     [Google Scholar]
  4. SchiaffellaF. MacchiaruloA. MilaneseL. VecchiarelliA. FringuelliR. Novel ketoconazole analogues based on the replacement of 2,4-dichlorophenyl group with 1,4-benzothiazine moiety: Design, synthesis, and microbiological evaluation.Bioorg. Med. Chem.200614155196520310.1016/j.bmc.2006.04.004 16650767
     [Google Scholar]
  5. CecchettiV. CalderoneV. TabarriniO. SabatiniS. FilipponiE. TestaiL. SpogliR. MartinottiE. FravoliniA. Highly potent 1,4-benzothiazine derivatives as K(ATP)-channel openers.J. Med. Chem.200346173670367910.1021/jm030791q 12904071
     [Google Scholar]
  6. MarchettiC. UlisseS. BruscoliS. RussoF.P. MiglioratiG. SchiaffellaF. CifoneM.G. RiccardiC. FringuelliR. Induction of apoptosis by 1,4-benzothiazine analogs in mouse thymocytes.J. Pharmacol. Exp. Ther.200230031053106210.1124/jpet.300.3.1053 11861815
     [Google Scholar]
  7. GowdaJ. KhaderA.M.A. KallurayaB. ShreeP. ShabarayaA.R. Synthesis, characterization and pharmacological activity of 4-[1-substituted aminomethyl-4-arylideneamino-5-sulfanyl-4,5-dihydro-1H-1,2,4-triazol-3-yl]m-ethyl-2H-1,4-benzothiazin-3(4H)-ones.Eur. J. Med. Chem.20114694100410610.1016/j.ejmech.2011.06.010 21724303
     [Google Scholar]
  8. DabholkarV.V. GavandeR.P. Synthesis and antimicrobial activities of novel 1,4-benzothiazine derivatives.Arab. J. Chem.20169S225S22910.1016/j.arabjc.2011.03.009
     [Google Scholar]
  9. WatanabeY. OsanaiK. NishiT. MiyawakiN. ShiiD. HondaT. ShibanoT. Synthesis of azido derivatives of semotiadil, a novel 1,4-benzothiazine calcium antagonist, for photoaffinity probes of calcium channels.Bioorg. Med. Chem. Lett.19966161923192610.1016/0960‑894X(96)00338‑1
     [Google Scholar]
  10. RaiA. SinghA.K. RajV. SahaS. 1,4-benzothiazines-a biologically attractive scaffold.Mini Rev. Med. Chem.20181814257 28552049
     [Google Scholar]
  11. WangX. HuangB. LiuX. ZhanP. Discovery of bioactive molecules from CuAAC click-chemistry-based combinatorial libraries.Drug Discov. Today201621111813210.1016/j.drudis.2015.08.004 26315392
     [Google Scholar]
  12. GaoP. SunL. ZhouJ. LiX. ZhanP. LiuX. Discovery of novel anti-HIV agents via Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry-based approach.Expert Opin. Drug Discov.201611985787110.1080/17460441.2016.1210125 27400283
     [Google Scholar]
  13. FuN. WangS. ZhangY. ZhangC. YangD. WengL. ZhaoB. WangL. Efficient click chemistry towards fatty acids containing 1,2,3-triazole: Design and synthesis as potential antifungal drugs for Candida albicans.Eur. J. Med. Chem.201713659660210.1016/j.ejmech.2017.05.001 28551587
     [Google Scholar]
  14. ZhangB. Comprehensive review on the anti-bacterial activity of 1,2,3-triazole hybrids.Eur. J. Med. Chem.201916835737210.1016/j.ejmech.2019.02.055 30826511
     [Google Scholar]
  15. YadavP. YadavJ.K. AgarwalA. AwasthiS.K. Insights into the interaction of potent antimicrobial chalcone triazole analogs with human serum albumin: spectroscopy and molecular docking approaches.RSC Advances2019955319693197810.1039/C9RA04192C 35530759
     [Google Scholar]
  16. BistrovićA. StipaničevN. Opačak-BernardiT. JukićM. MartinezS. Glavaš-ObrovacL. Raić-MalićS. Synthesis of 4-aryl-1,2,3-triazolyl appended natural coumarin-related compounds with antiproliferative and radical scavenging activities and intracellular ROS production modification.New J. Chem.201741157531754310.1039/C7NJ01469D
     [Google Scholar]
  17. XuZ. ZhaoS.J. LiuY. 1,2,3-Triazole-containing hybrids as potential anticancer agents: Current developments, action mechanisms and structure-activity relationships.Eur. J. Med. Chem.201918311170010.1016/j.ejmech.2019.111700 31546197
     [Google Scholar]
  18. FengL.S. ZhengM.J. ZhaoF. LiuD. 1,2,3‐triazole hybrids with anti‐HIV‐1 activity.Arch. Pharm.20213541200016310.1002/ardp.202000163 32960467
     [Google Scholar]
  19. RajR. SinghP. SinghP. GutJ. RosenthalP.J. KumarV. Azide-alkyne cycloaddition en route to 1H-1,2,3-triazole-tethered 7-chloroquinoline-isatin chimeras: Synthesis and antimalarial evaluation.Eur. J. Med. Chem.20136259059610.1016/j.ejmech.2013.01.032 23434528
     [Google Scholar]
  20. SharmaA. AgrahariA.K. RajkhowaS. TiwariV.K. Emerging impact of triazoles as anti-tubercular agent.Eur. J. Med. Chem.202223811445410.1016/j.ejmech.2022.114454 35597009
     [Google Scholar]
  21. KelleyJ.L. KobleC.S. DavisR.G. McLeanE.W. SorokoF.E. CooperB.R. 1-(Fluorobenzyl)-4-amino-1H-1,2,3-triazolo[4,5-c]pyridines: Synthesis and anticonvulsant activity.J. Med. Chem.199538204131413410.1021/jm00020a030 7562950
     [Google Scholar]
  22. Shareghi-BoroujeniD. IrajiA. MojtabaviS. FaramarziM.A. Akbarza deh, T.; Saeedi, M. Synthesis, in vitro evaluation, and molecular docking] studies of novel hydrazineylideneindolinone linked to phenoxymethyl-1,2,3-] triazole derivatives as potential α-glucosidase inhibitors.Bioorg. Chem.202111110486910.1016/j.bioorg.2021.104869 33839583
     [Google Scholar]
  23. MacanA.M. HarejA. CazinI. KlobučarM. StepanićV. PavelićK. PavelićS.K. ScholsD. SnoeckR. AndreiG. Raić-MalićS. Antitumor and antiviral activities of 4-substituted 1,2,3-triazolyl-2,3-dibenzyl-L-ascorbic acid derivatives.Eur. J. Med. Chem.201918411173910.1016/j.ejmech.2019.111739 31586832
     [Google Scholar]
  24. Sambasiva RaoP. KurumurthyC. VeeraswamyB. Santhosh KumarG. PoornachandraY. Ganesh KumarC. VasamsettiS.B. KotamrajuS. NarsaiahB. Synthesis of novel 1,2,3-triazole substituted-N-alkyl/aryl nitrone derivatives, their anti-inflammatory and anticancer activity.Eur. J. Med. Chem.20148018419110.1016/j.ejmech.2014.04.052 24780595
     [Google Scholar]
  25. a EllouzM. SebbarN.K. FichtaliI. OuzidanY. MennaneZ. CharofR. MagueJ.T. UrrutigoïtyM. EssassiE.M. Synthesis and antibacterial activity of new 1,2,3-triazolylmethyl-2H-1,4-benzothiazin-3(4H)-one derivatives.Chem. Cent. J.201812112310.1186/s13065‑018‑0494‑230499014
     [Google Scholar]
  26. b SebbarN.K. MekhzoumM.E.M. EssassiE.M. ZerzoufA. TalbaouiA. BakriY. SaadiM. AmmariL.E. Novel 1,4-benzothiazine derivatives: Synthesis, crystal structure, and anti-bacterial properties.Res. Chem. Intermed.20164296845686210.1007/s11164‑016‑2499‑6
     [Google Scholar]
  27. ShaikhM.H. SubhedarD.D. ArkileM. KhedkarV.M. JadhavN. SarkarD. ShingateB.B. Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent.Bioorg. Med. Chem. Lett.201626256156910.1016/j.bmcl.2015.11.071 26642768
     [Google Scholar]
  28. BorateH.B. MaujanS.R. SawargaveS.P. ChandavarkarM.A. VaiudeS.R. JoshiV.A. WakharkarR.D. IyerR. KelkarR.G. ChavanS.P. KunteS.S. Fluconazole analogues containing 2H-1,4-benzothiazin-3(4H)-one or 2H-1,4-benzoxazin-3(4H)-one moieties, a novel class of anti-Candida agents.Bioorg. Med. Chem. Lett.201020272272510.1016/j.bmcl.2009.11.071 19963383
     [Google Scholar]
  29. LiA.R. ZhangJ. GreenbergJ. LeeT. LiuJ. Discovery of non-glucoside SGLT2 inhibitors.Bioorg. Med. Chem. Lett.20112182472247510.1016/j.bmcl.2011.02.056 21398124
     [Google Scholar]
  30. FringuelliR. SchiaffellaF. BistoniF. PitzurraL. VecchiarelliA. Azole derivatives of 1,4-benzothiazine as antifungal agents.Bioorg. Med. Chem.19986110310810.1016/S0968‑0896(97)10016‑5 9502109
     [Google Scholar]
  31. SahooS.K. AhmadM.N. KaulG. NanduriS. DasguptaA. ChopraS. YaddanapudiV.M. Synthesis and evaluation of triazole congeners of nitro-benzothiazinones potentially active against drug resistant Mycobacterium tuberculosis demonstrating bactericidal efficacy.RSC Med. Chem.202213558559310.1039/D1MD00387A 35694687
     [Google Scholar]
  32. NeerajaP. SrinivasS. MukkantiK. DubeyP.K. PalS. 1H-1,2,3-Triazolyl-substituted 1,3,4-oxadiazole derivatives containing structural features of ibuprofen/naproxen: Their synthesis and antibacterial evaluation.Bioorg. Med. Chem. Lett.201626215212521710.1016/j.bmcl.2016.09.059 27727124
     [Google Scholar]
  33. WangG. PengZ. WangJ. LiX. LiJ. Synthesis, in vitro evaluation and molecular docking studies of novel triazine-triazole derivatives as potential α-glucosidase inhibitors.Eur. J. Med. Chem.201712542342910.1016/j.ejmech.2016.09.067 27689725
     [Google Scholar]
  34. FerroniC. PepeA. KimY.S. LeeS. GuerriniA. ParentiM.D. TeseiA. ZamagniA. CortesiM. ZaffaroniN. De CesareM. BerettaG.L. TrepelJ.B. MalhotraS.V. VarchiG. 1,4-substituted triazoles as nonsteroidal anti-androgens for prostate cancer treatment.J. Med. Chem.20176073082309310.1021/acs.jmedchem.7b00105 28272894
     [Google Scholar]
  35. SiddiquiM.A. NagargojeA.A. ShaikhM.H. SiddiquiR.A. PundA.A. KhedkarV.M. AsrondkarA. DeshpandeP.P. ShingateB.B. Design, synthesis and bioevaluation of highly functionalized 1,2,3-triazole-guanidine conjugates as anti-inflammatory and antioxidant agents.Polycycl. Aromat. Compd.20234365567558110.1080/10406638.2022.2105904
     [Google Scholar]
  36. ShaikhM.H. SubhedarD.D. AkolkarS.V. NagargojeA.A. KhedkarV.M. SarkarD. ShingateB.B. Tetrazoloquinoline-1,2,3-triazole derivatives as antimicrobial agents: Synthesis, biological evaluation and molecular docking study.Polycycl. Aromat. Compd.20224241920194110.1080/10406638.2020.1821229
     [Google Scholar]
  37. AkolkarS.V. NagargojeA.A. KrishnaV.S. SriramD. SangshettiJ.N. DamaleM. ShingateB.B. New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et3NH][OAc]-mediated efficient synthesis and biological evaluation.RSC Advances2019938220802209110.1039/C9RA03425K 35518861
     [Google Scholar]
  38. AkolkarS.V. NagargojeA.A. ShaikhM.H. WarshaghaM.Z.A. SangshettiJ.N. DamaleM.G. ShingateB.B. New N‐phenylacetamide‐linked 1,2,3‐triazole‐tethered coumarin conjugates: Synthesis, bioevaluation, and molecular docking study.Arch. Pharm.202035311200016410.1002/ardp.202000164 32776355
     [Google Scholar]
  39. AkolkarS.V. ShaikhM.H. BhalmodeM.K. PawarP.U. SangshettiJ.N. DamaleM.G. ShingateB.B. Click chemistry inspired syntheses of new amide linked 1,2,3-triazoles from naphthols: biological evaluation and in silico computational study.Res. Chem. Intermed.20234962725275310.1007/s11164‑023‑05008‑4
     [Google Scholar]
  40. ShaikhM.H. SubhedarD.D. NawaleL. SarkarD. KhanF.A.K. SangshettiJ.N. ShingateB.B. Novel benzylidenehydrazide-1,2,3-triazole conjugates as antitubercular agents: synthesis and molecular docking.Mini Rev. Med. Chem.201919141178119410.2174/1389557518666180718124858 30019644
     [Google Scholar]
  41. KhanZ.K. In vitro and vivo screening techniques for bioactivity screening and evaluation.Proceedings of the International Workshop UNIDO-CDRI1997210211
     [Google Scholar]
  42. SarkarS. SarkarD. Potential use of nitrate reductase as a biomarker for the identification of active and dormant inhibitors of Mycobacterium tuberculosis in a THP1 infection model.SLAS Discov.201217796697310.1177/1087057112445485 22573731
     [Google Scholar]
  43. LiS. LiD. XiaoT. ZhangS. SongZ. MaH. Design, synthesis, fungicidal activity, and unexpected docking model of the first chiral boscalid analogues containing oxazolines.J. Agric. Food Chem.201664468927893410.1021/acs.jafc.6b03464 27792876
     [Google Scholar]
  44. BuritsM. BucarF. Antioxidant activity of Nigella sativa essential oil.Phytother. Res.200014532332810.1002/1099‑1573(200008)14:5<323::AID‑PTR621>3.0.CO;2‑Q 10925395
     [Google Scholar]
  45. a HooftR.W.W. VriendG. SanderC. AbolaE.E. Errors in protein structures.Nature1996381658027227210.1038/381272a08692262
     [Google Scholar]
  46. b ShaikhM.H. SubhedarD.D. NawaleL. SarkarD. Kalam KhanF.A. SangshettiJ.N. ShingateB.B. 1,2,3-Triazole derivatives as antitubercular agents: synthesis, biological evaluation and molecular docking study.MedChemComm2015661104111610.1039/C5MD00057B
     [Google Scholar]
  47. LipinskiC.A. LombardoF. DominyB.W. FeeneyP.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings.Adv. Drug Deliv. Rev.2001461-332610.1016/S0169‑409X(00)00129‑0 11259830
     [Google Scholar]
/content/journals/coc/10.2174/0113852728316869240626060258
Loading
Synthesis and Biological Evaluation of 1,2,3-Triazole Appended Benzothiazinone Derivatives via Click Chemistry
Current Organic Chemistry 28, 1621 (2024); https://doi.org/10.2174/0113852728316869240626060258
/content/journals/coc/10.2174/0113852728316869240626060258
/content/journals/coc/10.2174/0113852728316869240626060258
Loading

Data & Media loading...

Supplements

file format download Download

  • Article Type:     Research Article
Keyword(s): 1,2,3-Triazoles; ADME; antifungal activity; benzothiazinone; molecular docking; rifampicin

Most Cited Most Cited RSS feed

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