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2000
Volume 22, Issue 3
  • ISSN: 1570-1638
  • E-ISSN: 1875-6220

Abstract

Background

The development of antimicrobial agents is crucial for several reasons, primarily to combat infectious diseases and to address the growing threat of antimicrobial resistance. The need for the continued development of antimicrobial drugs persists despite the presence of many existing drugs for several reasons, emerging new pathogens and diseases, resistance to existing drugs, and propagation of multidrug resistance to existing drugs.

Objective

The objective of the study was to synthesize and evaluate the antimicrobial potential of newly synthesized benzothiazole derivatives.

Methods

A new series of 2-(substituted amino)-N-(6-substituted-1,3-benzothiazol-2yl)acetamide BTC(a-t) has been synthesized by reacting it with chloracetyl chloride with substituted 2-amino benzothiazole and further refluxed with various substituted amines to obtain target compounds. The synthesized compounds were screened experimentally for their antimicrobial property against gram-positive and gram-negative bacteria and fungi. The zone of inhibition and minimum inhibitory concentration of compounds were determined against selected bacterial and fungal strains. Further docking study was carried out to check the probable interactions with the selected protein using V-life MDS 3.5 software (DNA gyrase, PDB: 3G75).

Results

Compounds BTC-j N-(6-methoxy-1,3-benzothiazol-2-yl)-2-(pyridine-3-ylamino)acetamide and BTC-r N-(6-nitro-1,3-benzothiazol-2-yl)-2-(pyridine-3-ylamino)acetamide were found to have good antimicrobial potential. The compound BTC-j showed good antibacterial activity against at an MIC value of 12.5 µg/mL, at MIC of 6.25µg/mL, at MIC of 3.125µg/mL, and at MIC of 6.25µg/mL. Thus, from the result, it was observed that compounds BTC-j, BTC-f, BTC-n, and BTC-r exhibited significant antibacterial and antifungal potential at different concentrations.

Conclusion

The present study resulted in the successful synthesis of 2-acetamido substituted benzothiazole derivatives BTC(a-t) with good yields. The dock score of the compounds and the antimicrobial activity were found to be consistent. No statistical difference in the antimicrobial activity of the standard and test compounds was found, indicating that the test compounds have comparable activity. Therefore, benzothiazole linked to heterocyclic rings with an acetamide linkage may serve as promising lead molecules for further optimization in the journey to discover potent antibacterial agents. Thus, we conclude that the synthesized compounds have the potential for further development as novel antimicrobial agents.

© 2025 Bentham Science Publishers
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2024-06-15
2025-09-05

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References

  1. CetinA. Pyrazole carboxylic acid and derivatives: Synthesis and biological applications.Mini Rev. Org. Chem.20211819310910.2174/1570193X17999200507094857
     [Google Scholar]
  2. CetinA. ToptasM. TürkanF. Synthesis, biological evaluation, and bioinformatics analysis of indole analogs on AChE and GST activities.Med. Chem. Res.202231122119213110.1007/s00044‑022‑02974‑z
     [Google Scholar]
  3. GilaniS.J. NagarajanK. DixitS.P. TaleuzzamanM. KhanS.A. Benzothiazole incorporated thiazolidin-4-ones and azetidin-2-ones derivatives: Synthesis and in vitro antimicrobial evaluation.Arab. J. Chem.20169S1523S153110.1016/j.arabjc.2012.04.004
     [Google Scholar]
  4. OuyangL. HuangY. ZhaoY. HeG. XieY. LiuJ. HeJ. LiuB. WeiY. Preparation, antibacterial evaluation and preliminary structure–activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives.Bioorg. Med. Chem. Lett.20122293044304910.1016/j.bmcl.2012.03.07922494615
     [Google Scholar]
  5. ArmeniseD. CarocciA. CatalanoA. MuragliaM. DefrenzaI. De LaurentisN. RosatoA. CorboF. FranchiniC. Synthesis and antimicrobial evaluation of a new series of N -1,3-Benzothiazol-2-ylbenzamides.J. Chem.201320131710.1155/2013/181758
     [Google Scholar]
  6. AsatiV. SahuN.K. RathoreA. SahuS. KohliD.V. Synthesis, characterization and antimicrobial evaluation of some 1,3-benzothiazole-2-yl-hydrazone derivatives.Arab. J. Chem.20158449549910.1016/j.arabjc.2011.01.036
     [Google Scholar]
  7. BhoiM.N. BoradM.A. ParmarH.B. PatelH.D. Synthesis and characterization of novel N-(Benzo[d]Thiazol-2-yl)-2-(2-(6-Chloroquinolin-4-yl)Hydrazinyl)acetamide derivatives containing quinoline linkage as potent antibacterial agents.Int. Lett. Chem. Phys. Astron.20155311412110.56431/p‑m6cnvs
     [Google Scholar]
  8. FranchiniC. MuragliaM. CorboF. FlorioM.A. Di MolaA. RosatoA. MatucciR. NesiM. van BambekeF. VitaliC. Synthesis and biological evaluation of 2-mercapto-1,3-benzothiazole derivatives with potential antimicrobial activity.Arch. Pharm.20093421060561310.1002/ardp.20090009219753564
     [Google Scholar]
  9. MorsyM.A. AliE.M. KandeelM. VenugopalaK.N. NairA.B. GreishK. El-DalyM. Screening and molecular docking of novel benzothiazole derivatives as potential antimicrobial agents.Antibiotics20209522110.3390/antibiotics905022132365587
     [Google Scholar]
  10. PadalkarV.S. BorseB.N. GuptaV.D. PhatangareK.R. PatilV.S. UmapeP.G. SekarN. Synthesis and antimicrobial activity of novel 2-substituted benzimidazole, benzoxazole and benzothiazole derivatives.Arab. J. Chem.20169S1125S113010.1016/j.arabjc.2011.12.006
     [Google Scholar]
  11. PereiraG.A. MassabniA.C. CastellanoE.E. CostaL.A.S. LeiteC.Q.F. PavanF.R. CuinA. A broad study of two new promising antimycobacterial drugs: Ag(I) and Au(I) complexes with 2-(2-thienyl)benzothiazole.Polyhedron201238129129610.1016/j.poly.2012.03.016
     [Google Scholar]
  12. YadavK.P. RahmanM.A. NishadS. MauryaS.K. AnasM. MujahidM. Synthesis and biological activities of benzothiazole derivatives: A review.Intel. Pharm.20232023S2949866X2300036910.1016/j.ipha.2023.06.001
     [Google Scholar]
  13. WangZ. ShiX.H. WangJ. ZhouT. XuY.Z. HuangT.T. LiY.F. ZhaoY.L. YangL. YangS.Y. YuL.T. WeiY.Q. Synthesis, structure–activity relationships and preliminary antitumor evaluation of benzothiazole-2-thiol derivatives as novel apoptosis inducers.Bioorg. Med. Chem. Lett.20112141097110110.1016/j.bmcl.2010.12.12421262571
     [Google Scholar]
  14. AmmazzalorsoA. CarradoriS. AmorosoR. FernándezI.F. 2-substituted benzothiazoles as antiproliferative agents: Novel insights on structure-activity relationships.Eur. J. Med. Chem.202020711276210.1016/j.ejmech.2020.11276232898763
     [Google Scholar]
  15. NavaleA. PawarS. DeodharM. KaleA. Synthesis of substituted benzo[d]thiazol-2-ylcarbamates as potential anticonvulsants.Med. Chem. Res.20132294316432110.1007/s00044‑012‑0434‑y
     [Google Scholar]
  16. KaleA. KakdeR. PawarS. ThombareR. Recent development in substituted benzothiazole as an anticonvulsant agent.Mini Rev. Med. Chem.20212181017102410.2174/138955752166620122214523633355052
     [Google Scholar]
  17. PatilV.S. NandreK.P. GhoshS. RaoV.J. ChopadeB.A. SridharB. BhosaleS.V. BhosaleS.V. Synthesis, crystal structure and antidiabetic activity of substituted (E)-3-(Benzo [d]thiazol-2-ylamino) phenylprop-2-en-1-one.Eur. J. Med. Chem.20135930430910.1016/j.ejmech.2012.11.02023262035
     [Google Scholar]
  18. Navarrete-VazquezG. Ramírez-MartínezM. Estrada-SotoS. Nava-ZuazoC. PaoliP. CamiciG. Escalante-GarcíaJ. Medina-FrancoJ.L. López-VallejoF. Ortiz-AndradeR. Synthesis, in vitro and in silico screening of ethyl 2-(6-substituted benzo[d]thiazol-2-ylamino)-2-oxoacetates as protein-tyrosine phosphatase 1B inhibitors.Eur. J. Med. Chem.20125334635510.1016/j.ejmech.2012.04.02522583779
     [Google Scholar]
  19. NagarajanS.R. De CrescenzoG.A. GetmanD.P. LuH.F. SikorskiJ.A. WalkerJ.L. McDonaldJ.J. HousemanK.A. KocanG.P. KishoreN. MehtaP.P. Funkes-ShippyC.L. BlystoneL. Discovery of novel benzothiazolesulfonamides as potent inhibitors of HIV-1 protease.Bioorg. Med. Chem.200311224769477710.1016/j.bmc.2003.07.00114556792
     [Google Scholar]
  20. ShafiS. Mahboob AlamM. MulakayalaN. MulakayalaC. VanajaG. KalleA.M. PalluR. AlamM.S. Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: Their anti-inflammatory and anti-nociceptive activities.Eur. J. Med. Chem.20124932433310.1016/j.ejmech.2012.01.03222305614
     [Google Scholar]
  21. ÖztürkF. AçikL. Şenerİ. KarciF. KiliçE. Antimicrobial properties and DNA interactions studies of 3-hetarylazoquinoline-2,4-diol compounds.Turk. J. Chem.201236229330210.3906/kim‑1107‑14
     [Google Scholar]
  22. 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.2009.12.01620056520
     [Google Scholar]
  23. Pooja Pisal, Meenakshi Deodhar, Amol Kale, Ganesh Nigade, Smita Pawar; Design, synthesis, docking studies and biological evaluation of 2-phenyl-3- (Substituted benzo[d] thiazol-2-ylamino)-quinazoline-4(3h)-one derivatives as antimicrobial agents.Int. J. Pharm. Pharm. Sci.201810576110.22159/ijpps.2018v10i10.28480
     [Google Scholar]
  24. ImranM. KhanS.A. Synthesis and antimicrobial activity of some 2-amino-4-(7- substituted/unsubstituted coumarin-3-yl)-6-(chlorosubstitutedphenyl) pyrimidines.Trop. J. Pharm. Res.2015147126510.4314/tjpr.v14i7.20
     [Google Scholar]
  25. PatelN.B. AgravatS.N. ShaikhF.M. Synthesis and antimicrobial activity of new pyridine derivatives-I.Med. Chem. Res.20112071033104110.1007/s00044‑010‑9440‑0
     [Google Scholar]
  26. YangX. PengT. YangY. LiW. XiongJ. ZhaoL. DingZ. Antimicrobial and antioxidant activities of a new benzamide from endophytic Streptomyces sp. YIM 67086.Nat. Prod. Res.201529433133510.1080/14786419.2014.94517425109748
     [Google Scholar]
  27. KhanT. SankheK. SuvarnaV. SherjeA. PatelK. DravyakarB. DNA gyrase inhibitors: Progress and synthesis of potent compounds as antibacterial agents.Biomed. Pharmacother.201810392393810.1016/j.biopha.2018.04.02129710509
     [Google Scholar]
  28. OblakM. GrdadolnikS.G. KotnikM. JeralaR. FilipičM. ŠolmajerT. In silico fragment-based discovery of indolin-2-one analogues as potent DNA gyrase inhibitors.Bioorg. Med. Chem. Lett.200515235207521010.1016/j.bmcl.2005.08.06816203145
     [Google Scholar]
  29. RonkinS.M. BadiaM. BellonS. GrillotA.L. GrossC.H. GrossmanT.H. ManiN. ParsonsJ.D. StamosD. TrudeauM. WeiY. CharifsonP.S. Discovery of pyrazolthiazoles as novel and potent inhibitors of bacterial gyrase.Bioorg. Med. Chem. Lett.20102092828283110.1016/j.bmcl.2010.03.05220356737
     [Google Scholar]
  30. JimonetP. AudiauF. BarreauM. BlanchardJ.C. BoireauA. BourY. ColénoM.A. DobleA. DoerflingerG. Do HuuC. DonatM.H. DuchesneJ.M. GanilP. GuérémyC. HonoréE. JustB. KerphiriqueR. GontierS. HubertP. LaduronP.M. Le BlevecJ. MeunierM. MiquetJ.M. NemecekC. PasquetM. PiotO. PrattJ. RataudJ. ReibaudM. StutzmannJ-M. MignaniS. Riluzole series. Synthesis and in vivo “antiglutamate” activity of 6-substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines.J. Med. Chem.199942152828284310.1021/jm980202u10425092
     [Google Scholar]
  31. SalviV. BhambiD. JatJ. TalesaraG. Synthesis and antimicrobial activity of some 2-[1-(4-oxo-3,4-dihydrophthalazine-1-yl)alkyl]-1h-isoindole-1,3(2h)-dione and their imidoxy derivatives.ARKIVOC200614133140
     [Google Scholar]
  32. PatelH.S. DesaiH.D. MistryH.J. Synthesis and antimicrobial activity of some new piperazine derivaties containing aryl sulfonyloxy group.E-J. Chem.200412939810.1155/2004/732420
     [Google Scholar]
  33. Rodríguez-TudelaJ.L. BarchiesiF. BilleJ. ChryssanthouE. Cuenca-EstrellaM. DenningD. DonnellyJ.P. DupontB. FegelerW. MooreC. RichardsonM. VerweijP.E. Method for the determination of minimum inhibitory concentration (MIC) by broth dilution of fermentative yeasts.Clin. Microbiol. Infect.200398iviii10.1046/j.1469‑0691.2003.00789.x
     [Google Scholar]
  34. MohanV. GibbsA. CummingsM. JaegerE. DesJarlaisR. Docking: Successes and challenges.Curr. Pharm. Des.200511332333310.2174/138161205338210615723628
     [Google Scholar]
  35. SrivastavaV. GuptaS.P. SiddiqiM.I. MishraB.N. Molecular docking studies on quinazoline antifolate derivatives as human thymidylate synthase inhibitors.Bioinformation20104835736510.6026/9732063000435720975900
     [Google Scholar]
  36. NoolviM.N. PatelH.M. A comparative QSAR analysis and molecular docking studies of quinazoline derivatives as tyrosine kinase (EGFR) inhibitors: A rational approach to anticancer drug design.J. Saudi Chem. Soc.201317436137910.1016/j.jscs.2011.04.017
     [Google Scholar]
  37. PradhanA. VishwakarmaS.K. Synthesis of quinolone derivatives and their molecular docking for antiepileptic activity.Chem. Int.20206422423110.5281/ZENODO.3700632
     [Google Scholar]
/content/journals/cddt/10.2174/0115701638299377240604112400
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Synthesis, Molecular Docking, and Antimicrobial Evaluation of 2-(Substituted Amino)-N-(6-Substituted-1,3-Benzothiazol-2yl) Acetamide
Current Drug Discovery Technologies 22, E200624231065 (2025); https://doi.org/10.2174/0115701638299377240604112400
/content/journals/cddt/10.2174/0115701638299377240604112400
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  • Article Type:     Research Article
Keyword(s): acetamide; antimicrobial; Benzothiazole; DNA gyrase; docking; V-life MDS

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