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2000
Volume 29, Issue 16
  • ISSN: 1385-2728
  • E-ISSN: 1875-5348

Abstract

Variously substituted benzothiazolamines were prepared and employed as starting material to synthesize some new benzothiazolamine-based bis-thiourea derivatives, such as 3, 3’-bis(6-substituted benzothiazolyl)terephthaloyl-bis(thioureas). Molecular modeling of all the synthesized compounds was carried out to check the interactions of all the bis-thiourea ligands inside the active pocket of enzyme 3MNG in comparison to competitive antioxidant inhibitor DTT (1,2-dithiane-4,5-diol). The antioxidant activities of all the synthesized compounds were determined using a DPPH radical assay performed by standard methods. Benzothiazole-based bis-thiourea derivatives exhibited significant potent antioxidant properties.

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2025-01-31
2025-09-01

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References

  1. PatelN.B. ShaikhF.M. New 4-thiazolidinones of nicotinic acid with 2-amino-6-methylbenzothiazole and their biological activity.Sci. Pharm.201078475376510.3797/scipharm.1009‑15 21179315
     [Google Scholar]
  2. GuptaS AjmeraN GautamN SharmaR GauatamD Novel synthesis and biological activity study of pyrimido[2,1-b] benzothiazoles.Ind J Chem200948B85358
     [Google Scholar]
  3. ReddyP. LinY. ChangH. Synthesis of novel benzothiazole compounds with an extended conjugated system.Arcivoc2007xvi113122
     [Google Scholar]
  4. PiscitelliF. BallatoreC. SmithA.B.III Solid phase synthesis of 2-aminobenzothiazoles.Bioorg. Med. Chem. Lett.201020264464810.1016/j.bmcl.2009.11.055 19954974
     [Google Scholar]
  5. ChaudharyP. SharmaP. SharmaA. VarshneyJ. Recent advances in pharmacological activity of benzothiazole derivatives.Int. J. Curr. Pharm. Res.201024511
     [Google Scholar]
  6. RanaA. SiddiquiN. KhanS.A. Benzothiazoles: A new profile of biological activities.Ind. J. Pharm. Sci.20076911017
     [Google Scholar]
  7. MalikJ.K. ManviF.V. NanjwadeB.K. New 2-amino substituted benzothiazoles: A new profile of biological activities.J. Pharm. Res.200921116871690
     [Google Scholar]
  8. MalikJ.K. ManviF.V. NanjwadeB.K. SinghS. PurohitP. Review of the 2-amino substituted benzothiazoles: Different methods of the synthesis.Pharm. Lett.201021347359
     [Google Scholar]
  9. PatrickJ. Synthesis and in vivo “Antiglutamate” activity of 6-substituted-2-benzothiazolamines and 3-substituted-2-iminobenzothiazolines.J. Med. Chem.199942152828284310.1021/jm980202u 10425092
     [Google Scholar]
  10. BrysonH.M. FultonB. BenfieldP. Riluzole.Drugs199652454956310.2165/00003495‑199652040‑00010 8891467
     [Google Scholar]
  11. PittengerC. CoricV. BanasrM. BlochM. KrystalJ.H. SanacoraG. Riluzole in the treatment of mood and anxiety disorders.CNS Drugs200822976178610.2165/00023210‑200822090‑00004 18698875
     [Google Scholar]
  12. GuptaA. RawatS. Synthesis and cyclization of benzothiazole.J. Curr. Pharm. Res.201031323
     [Google Scholar]
  13. AkhileshG. SwatiR. Therapeutic importance of benzothiazole.Asian J. Res. Chem20103821836
     [Google Scholar]
  14. Priyanka; Sharma, NK; Jha, KK. Benzothiazole: The molecule of diverse biological activities.Int. J. Curr. Pharm. Res.20102216
     [Google Scholar]
  15. SuccawG.L. WeakleyT.J.R. HanF. DoxseeK.M. Crystal engineering with bis(thiourea) derivatives.Cryst. Growth Des.2005562288229810.1021/cg050162c
     [Google Scholar]
  16. BerkesselA. RolandK. NeudörflJ.M. Asymmetric Morita-Baylis-Hillman reaction catalyzed by isophoronediamine-derived bis(thio)urea organocatalysts.Org. Lett.20068194195419810.1021/ol061298m 16956185
     [Google Scholar]
  17. ShingJ.C. ChoiJ.W. ChapmanR. SchroederM.A. SarkariaJ.N. FauqA. BramR.J. A novel synthetic 1,3-phenyl bis-thiourea compound targets microtubule polymerization to cause cancer cell death.Cancer Biol. Ther.201415789590510.4161/cbt.28881 24755487
     [Google Scholar]
  18. ZullkipleeW.W.S.H. HalimA.A.N. NgainiZ. AriffM.M.A. HussainH. Bis-Thiourea bearing aryl and amino acids side chains and their antibacterial activities.Phosph. Sulfur Silicon Relat. Elem.2014189683283810.1080/10426507.2013.858250
     [Google Scholar]
  19. SaturninoC. D’AuriaM. PaesanoN. SaponieroD. CioffiG. BuonerbaM. MartinoD.G. Antioxidant activity of thioureidic derivatives I.Farmaco200358982382810.1016/S0014‑827X(03)00139‑3 13679175
     [Google Scholar]
  20. VenkateshP. PandeyaS.N. Synthesis and anti-oxidant activity of some N-(anilinocarbonothioyl) benzamide and heterocyclic based thiourea derivatives.Inter. J. Chem. Tech. Res.200913733741
     [Google Scholar]
  21. HalimN.I.M. KassimK. FadzilA.H. YaminB.M. Synthesis, characterisation and antibacterial studies of Cu(II) complexes thiourea.Malays. J. Anal. Sci.20121615661
     [Google Scholar]
  22. WuJ. ShiQ. ChenZ. HeM. JinL. HuD. Synthesis and bioactivity of pyrazole acyl thiourea derivatives.Molecules20121755139515010.3390/molecules17055139 22555301
     [Google Scholar]
  23. KaswalaP.B. ChikhaliaK.H. ShahN.K. PatelD.P. PatelD.H. MudaliarG.V. Design, synthesis and antimicrobial evaluation of s-triazinyl urea and thiourea derivatives.ARKIVOC200920091132633510.3998/ark.5550190.0010.b30
     [Google Scholar]
  24. NgainiZ. ArifM.M.A. HussainH. MeiE.S. TangD. KamaluddinD.H.A. Synthesis and antibacterial activity of acetoxybenzoyl thioureas with aryl and amino acid side chains.Phosphorus Sulfur Silicon Relat. Elem.201218711710.1080/10426507.2011.562398
     [Google Scholar]
  25. UckunF.M. MaoC. PendergrassS. MaherD. ZhuD. AhlgrenT.L. VenkatachalamT.K. N-[2-(4-methylphenyl)ethyl]-N′-[2-(5-bromopyridyl)]-thiourea as a potent inhibitor of NNRTI-resistant and multidrug-resistant human immunodeficiency virus type 1.Antivir. Chem. Chemother.200011213514010.1177/095632020001100205 10819437
     [Google Scholar]
  26. Küçükgüzelİ. TatarE. KüçükgüzelŞ.G. RollasS. ClercqD.E. Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents.Eur. J. Med. Chem.200843238139210.1016/j.ejmech.2007.04.010 17583388
     [Google Scholar]
  27. HalimN.I.M. KassimK. FadzilA.H. YaminB.M. Synthesis, characterization and antibacterial studies of benzoylthiourea derivatives.IPCBEE2011145559
     [Google Scholar]
  28. ZhongZ. XingR. LiuS. WangL. CaiS. LiP. Synthesis of acyl thiourea derivatives of chitosan and their antimicrobial activities in vitro.Carbohydr. Res.2008343356657010.1016/j.carres.2007.11.024 18083151
     [Google Scholar]
  29. SaeedS. RashidN. JonesP.G. AliM. HussainR. Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents.Eur. J. Med. Chem.20104541323133110.1016/j.ejmech.2009.12.016 20056520
     [Google Scholar]
  30. MolotoM.L. RevaprasaduN.J. N-alkylthioureacadmium (II) complexes as novel precursors for the synthesis of CdS nanoparticles.Mater. Sci.200415313316
     [Google Scholar]
  31. AtiaA.A. Adsorption of silver(I) and gold(III) on resins derived from bisthiourea and application to retrieval of silver ions from processed photo films.Hydrometallurgy2005801-29810610.1016/j.hydromet.2005.07.004
     [Google Scholar]
  32. PhetsuksiriB. JacksonM. SchermanH. McNeilM. BesraG.S. BaulardA.R. SlaydenR.A. DeBarberA.E. BarryC.E.III BairdM.S. CrickD.C. BrennanP.J. Unique mechanism of action of the thiourea drug isoxyl on Mycobacterium tuberculosis.J. Biol. Chem.200327852531235313010.1074/jbc.M311209200 14559907
     [Google Scholar]
  33. LiD. LongD. FuH. The synthesis and fungicidal activities of 2,6-Bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]pyridines.Phosphorus Sulfur Silicon Relat. Elem.200618192079208710.1080/10426500600605830
     [Google Scholar]
  34. KhaledE. HassanH. GirgisA. MetelkaR. Construction of novel simple phosphate screen-printed and carbon paste ion-selective electrodes.Talanta200877273774310.1016/j.talanta.2008.07.018
     [Google Scholar]
  35. GirgisA.S. Facile synthesis of dithiatetraaza-macrocycles of potential anti-inflammatory activity.Eur. J. Med. Chem.200843102116212110.1016/j.ejmech.2007.12.010 18242783
     [Google Scholar]
  36. ManjuS.L. AshaS. RejiT.F.A.F. RajasekharanK.N. Synthesis of novel 1,4-bis[(5-aroyl-2-N,N-disubstituted amino)thiazol-4-yl]benzenes.ARKIVOC2008xv288296
     [Google Scholar]
  37. LeonovaE.S. MakarovM.V. RybalkinaE.Y. NayaniS.L. TongwaP. FonariA. TimofeevaT.V. OdinetsI.L. Structure–cytotoxicity relationship in a series of N-phosphorus substituted E,E-3,5-bis(3-pyridinylmethylene)- and E,E-3,5-bis(4-pyridinylmethylene)piperid-4-ones.Eur. J. Med. Chem.201045125926593410.1016/j.ejmech.2010.09.058 21035234
     [Google Scholar]
  38. OppermanT.J. WilliamsJ.D. HouseweartC. PanchalR.G. BavariS. PeetN.P. MoirD.T. BowlinT.L. Efflux-mediated bis-indole resistance in Staphylococcus aureus reveals differential substrate specificities for MepA and MepR.Bioorg. Med. Chem.20101862123213010.1016/j.bmc.2010.02.005 20188576
     [Google Scholar]
  39. MenaM.L. CarraleroV. CortésG.A. SedeñoY.P. PingarrónJ.M. Bioelectrochemical evaluation of the total phenols content in olive oil mill wastewaters using a tyrosinase–colloidal gold–graphite–Teflon biosensor.Int. J. Environ. Anal. Chem.2007871576510.1080/03067310600833385
     [Google Scholar]
  40. BuschJ.L.H.C. HrncirikK. BulukinE. BouconC. MasciniM. Biosensor measurements of polar phenolics for the assessment of the bitterness and pungency of virgin olive oil.J. Agric. Food Chem.200654124371437710.1021/jf060103m 16756369
     [Google Scholar]
  41. HalvorsenB.L. HolteK. MyhrstadM.C.W. BarikmoI. HvattumE. RembergS.F. WoldA.B. HaffnerK. BaugerødH. AndersenL.F. MoskaugØ. JacobsD.R.Jr BlomhoffR. A systematic screening of total antioxidants in dietary plants.J. Nutr.2002132346147110.1093/jn/132.3.461 11880572
     [Google Scholar]
  42. BastA. HaenenG.R.M.M. BruynzeelA.M.E. VijghV.D.W.J.F. Protection by flavonoids against anthracycline cardiotoxicity: From chemistry to clinical trials.Cardiovasc. Toxicol.20077215415910.1007/s12012‑007‑0018‑0 17652822
     [Google Scholar]
  43. Rafique*, H; Tahira, F; Afshan, SZ Synthesis, molecular docking, and in vitro investigation of 1,1′-Diaryl-3,3′-(p-phenylenedicarbonyl) dithioureas as urease inhibitors.Lett. Org. Chem.2020174254259
     [Google Scholar]
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Efficient Synthesis, Characterization, and Molecular Docking Studies of Some Novel Benzothiazolamine-based Terephthaloyl Bisthioureas and Investigation of their Potent Antioxidant Activities
Current Organic Chemistry 29, 1270 (2025); https://doi.org/10.2174/0113852728273718241216070432
/content/journals/coc/10.2174/0113852728273718241216070432
/content/journals/coc/10.2174/0113852728273718241216070432
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  • Article Type:     Research Article
Keyword(s): 3MNG enzyme; antioxidant properties; Benzothiazolamines; benzothiazolyl thioureas; molecular docking; terephthaloyl-bis(thioureas)

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