Skip to main content
SpringerLink
Log in

Synthesis and antibacterial activity of benzothiazole and benzoxazole-appended substituted 1,2,3-triazoles

  • Regular Article
  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

A series of benzothiazole and benzoxazole linked 1,4-disubstituted 1,2,3-triazoles was synthesized through copper(I) catalyzed azide-alkyne cycloaddition reaction. FTIR, 1H, 13C-NMR and HRMS techniques were used to examine the structure of synthesized derivatives. Further, these triazole derivatives were screened for in vitro antibacterial activities against two Gram-positive bacteria S. aureus, B. subtilis; two Gram-negative bacteria E. coli and K. pneumoniae by serial dilution technique, reflecting moderate to good activity. Compound 7s exhibited promising antibacterial activity among all the synthesized triazoles.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1
Figure 2
Figure 3
Figure 4
Scheme 1

Similar content being viewed by others

Abbreviations

MIC:

Minimum Inhibitory Concentration

MTCC:

Microbial Type Culture Concentration

NCDC:

National Collection of Dairy Culture

References

  1. Singh G, Chowdhary K, Satija P, Singh A, Singh B, Singh K, Espinosa C B, Esteban M A, Sehgal R and Verma V 2018 Synthesis and immobilization of benzothiazole-appended triazole-silane: Biological evaluation and molecular docking approach Chem. Select 3 1609

    CAS  Google Scholar 

  2. Kumbhare R M, Dadmal T, Kosurkar U, Sridhar V and Rao J V 2012 Synthesis and cytotoxic evaluation of thiourea and N-bis-benzothiazole derivatives: A novel class of cytotoxic agents Bioorg. Med. Chem. Lett. 22 453

    Article  CAS  Google Scholar 

  3. Aouad M R, Soliman M A, Alharbi M O, Bardaweel S K, Sahu P K, Ali A A, Messali M, Rezki N and Soud Y A A 2018 Design, synthesis and anticancer screening of novel benzothiazole-piperazine-1,2,3-triazole hybrids Molecules 23 2788

  4. Santhoshi A and Alam H 2014 Synthesis of thio-pyrimidine, benzoxazole, benzothiazole and triazole analogues from Baylis-Hillman Bromides as potent cyclooxygenase-2 inhibitors J. Chem. Pharm. Sci. 2014 Special Issue

  5. Chandramouli, Shivanand M R, Nayanbhai T B, Bheemachari and Udupi R H 2012 Synthesis and biological screening of certain new triazole schiff bases and their derivatives bearing substituted benzothiazole moiety J. Chem. Pharm. Res. 4 1151

    CAS  Google Scholar 

  6. Faraji L, Shahkarami S, Nadri H, Moradi A, Saeedi M, Foroumadi A, Ramazani A, Haririan I, Ganjali M R, Shafiee A and Khoobi M 2017 Synthesis of novel benzimidazole and benzothiazole derivatives bearing a 1,2,3-triazole ring system and their acetylcholinesterase inhibitory activity J. Chem. Res. 41 30

    Article  CAS  Google Scholar 

  7. Raju K S, Reddy S A, Sabitha G, Krishna V S, Sriram D, Reddy K B and Sagurthi S R 2019 Synthesis and biological evaluation of 1H-pyrrolo[2,3-d]pyrimidine-1,2,3-triazole derivatives as novel anti-tubercular agents Bioorg. Med. Chem. Lett. 29 284

    Article  Google Scholar 

  8. Li H, Wang H, Wang Z, Yan H, Zhang M, Liu Y and Cheng M 2018 Synthesis, antitumor activity evaluation and mechanistic study of novel hederacolchiside A1 derivatives bearing an aryl triazole moiety Bioorg. Med. Chem. 26 4025

    Article  CAS  Google Scholar 

  9. Gilandoust M, Harsha K B, Mohan C D, Raquib A R, Rangappa S, Pandey V, Lobie P E, Basappa and Rangappa K S 2018 Synthesis, characterization and cytotoxicity studies of 1,2,3-triazoles and 1, 2,4-triazolo [1,5-a] pyrimidines in human breast cancer cells Bioorg. Med. Chem. Lett. 28 2314

    Article  CAS  Google Scholar 

  10. Shankaraiah N, Kumar N P, Tokala R, Gayatri B S, Talla V and Santos L S 2019 Synthesis of new 1,2,3-triazolo-naphthalimide/phthalimide conjugates via ‘click’ reaction: DNA intercalation and cytotoxic studies J. Braz. Chem. Soc. 30 454

    CAS  Google Scholar 

  11. Lu G Q, Li X Y, Mohamed O K, Wang D and Meng F H 2019 Design, synthesis and biological evaluation of novel uracil derivatives bearing 1, 2, 3-triazole moiety as thymidylate synthase (TS) inhibitors and as potential antitumor drugs Eur. J. Med. Chem. 171 282

    Article  CAS  Google Scholar 

  12. Pasupuleti B G, Khongsti K, Das B and Bez G 2020 1, 2, 3-Triazole tethered 1, 2, 4-trioxanes: Studies on their synthesis and effect on osteopontin expression in MDA-MB-435 breast cancer cells Eur. J. Med. Chem. 186 111908

    Article  CAS  Google Scholar 

  13. Shinoda K, Kanai M and Sohma Y 2020 Design, synthesis, and properties of a chemically-tethered amyloid-β segment trimer resistant to inter-trimer mis-aggregation J. Org. Chem. 85 1635

    Article  CAS  Google Scholar 

  14. Zimmermann L A, Moraes M H, Rosa R, Melo E B, Paula F R, Schenkela E P Steindel, M and Bernardes L S C 2018 Synthesis and SAR of new isoxazole-triazole bis-heterocyclic compounds as analogues of natural lignans with antiparasitic activity Bioorg. Med. Chem. 26 4850

    Article  CAS  Google Scholar 

  15. Tan W, Li Q, Dong F, Zhanga J, Luana F, Wei L, Chena Y and Guo Z 2018 Novel cationic chitosan derivative bearing 1,2,3-triazolium and pyridinium: Synthesis, characterization, and antifungal property Carbohydr. Polym. 182 180

    Article  CAS  Google Scholar 

  16. Govindaiah S, Sreenivasa S, Ramakrishna R A, Rao T M C and Nagabhushana H 2018 Regioselective synthesis, antibacterial, molecular docking and fingerprint applications of 1-benzhydrylpiperazine derivatized 1,4-disubstituted 1,2,3-triazoles Chem. Select 3 8111

  17. Zhou J, Stapleton P, Haider S and Healy J 2018 Boronic acid inhibitors of the class A b-lactamase KPC-2 Bioorg. Med. Chem. 26 2921

    Article  CAS  Google Scholar 

  18. Abbaspour S, Keivanloo A, Bakherad M and Sepehri S 2019 Salophen copper(II) complex-assisted click reactions for fast synthesis of 1,2,3-triazoles based on naphthalene-1,4-dione scaffold, antibacterial evaluation, and molecular docking studies Chem. Biodivers. 16 e1800410

    PubMed  Google Scholar 

  19. Kaushik C P, Luxmi R, Kumar A, Kumar K and Pahwa A 2019 Antibacterial evaluation and QSAR studies of 1,2,3-triazole bridged with amide functionality Indian J. Chem. 58B 88

    CAS  Google Scholar 

  20. Torres L M F C, Almeida M T, Santos T L, Marinho L E S, Mesquita J P, Silva L M, Santos W T P, Martins H R, Kato K C, Alves E S F, Liao L M, Magalhaes M T Q, Mendonça F G, Pereira F V, Resende J M, Bemquerer M P, Rodrigues M A and Verly R M 2019 Antimicrobial alumina nanobiostructures of disulfide- and triazole-linked peptides: Synthesis, characterization, membrane interactions and biological activity Colloids Surf. B 177 94

  21. Bommagani M B, Mokenapelli S, Yerrabelli J R, Boda S K and Chitneni P R 2020 Novel 4-(1H-1, 2, 3-triazol-4-yl) methoxy) cinnolines as potent antibacterial agents: Synthesis and molecular docking study Synth. Commun. 50 1016

    Article  CAS  Google Scholar 

  22. Deswal S, Naveen, Tittal R K, Vikas D G, Lal K and Kumar A 2020 5-Fluoro-1H-indole-2, 3-dione-triazoles-synthesis, biological activity, molecular docking, and DFT study J. Mol. Struct. 1209 127982

    Article  CAS  Google Scholar 

  23. Gontijo V S, Espuri P F, Alves R B, Camargos L F, Santos F V, Alves W, Marques M and Freitas R 2015 Leishmanicial, antiproteolytic, and mutagenic evaluation of alkyltriazoles and alkylphosphocholines Eur. J. Med. Chem. 101 24

    Article  CAS  Google Scholar 

  24. Bonache M A, Fernandez S M, Miguel M, Munoz B S and Muniz R G 2018 Small library of triazolyl polyphenols correlating antioxidant activity and stability with number and position of hydroxyl groups ACS Comb. Sci. 20 694

    Article  CAS  Google Scholar 

  25. Kaushik C P and Luxmi R 2020 Synthesis, antibacterial, and antioxidant activities of naphthyl‐linked disubstituted 1,2,3‐triazoles J. Het. Chem. 57 2400

    Article  CAS  Google Scholar 

  26. Kumar A K, Sunitha V, Shankar B, Ramesh M, Krishna T M and Jalapathi P 2016 Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel 1,2,3-Triazole Derivatives as Potent Anti-Inflammatory Agents Russ. J. Gen. Chem. 86 1154

    Article  Google Scholar 

  27. Maurent K, Bacque C V, Baltas M, Salvayre A N, Auge N and Belval F B 2018 Synthesis and biological evaluation of diarylheptanoids as potential antioxidant and anti-inflammatory agents Eur. J. Med. Chem. 144 289

    Article  CAS  Google Scholar 

  28. Litchfield M, Wuest M, Glubrecht D and Wues F 2020 Radiosynthesis and Biological Evaluation of [18F] Triacoxib: A New Radiotracer for PET Imaging of COX-2 Mol. Pharm. 17 251

    Article  CAS  Google Scholar 

  29. Sahu A, Das D, Sahu P, Mishra S, Sakthivel A, Gajbhiye A and Agrawal R 2020 Bioisosteric replacement of amide group with 1,2,3-triazoles in acetaminophen addresses reactive oxygen species-mediated hepatotoxic insult in Wistar albino rats Chem. Res. Toxicol. 33 522

    Article  CAS  Google Scholar 

  30. Devender N, Gunjan S, Tripathi R and Tripathi R P 2017 Synthesis and antiplasmodial activity of novel indoleamide derivatives bearing sulfonamide and triazole pharmacophores Eur. J. Med. Chem. 131 171

    Article  CAS  Google Scholar 

  31. Wang G, Peng Z, Wang J, Li X and Li J 2017 Synthesis, in vitro evaluation and molecular docking studies of novel triazine-triazole derivatives as potent α-glycosidase inhibitors Eur. J. Med. Chem. 125 423

    Article  CAS  Google Scholar 

  32. Tian Y, Liu Z, Liu J, Huang B, Kang D, Zhang H, Clercq E D, Daelemans D, Pannecouque C, Lee K H Chen C H Zhan P and Liu X 2018 Targeting the entrance channel of NNIBP: Discovery of diarylnicotinamide 1,4-disubstituted 1,2,3-triazoles as novel HIV-1 NNRTIs with high potency against wildtype and E138K mutant virus Eur. J. Med. Chem. 151 339

    Article  CAS  Google Scholar 

  33. Tantray M A, Khan I, Hamid H, Alam M S, Dhulap A and Kalam A 2016 Synthesis of benzimidazole-based 1,3,4-oxadiazole-1,2,3-triazole conjugates as glycogen synthase kinase-3β inhibitors with antidepressant activity in in vivo models RSC Adv. 6 43345

  34. Bagheri S M, Khoobi M, Nadri H, Moradi A, Emami S, Baleh L J, Jafarpour F, Moghadam F H, Foroumadi A and Shafie A 2015 Synthesis and anticholinergic activity of 4-hydroxycoumarin derivatives containing substituted benzyl-1,2,3-triazole moiety Chem. Biol. Drug Des. 86 1215

    Article  CAS  Google Scholar 

  35. Fatih C, Yasemin U, Burak B, Arzu O and Kemal S 2018 Synthesis, characterization and biological activities of new symmetric bis-1,2,3-triazoles with click chemistry Med. Chem. 14 230

    Article  Google Scholar 

  36. Shafi S, Alam M M, Mulakayala N, Mulakayala C, Vanaja G, Kalle A M, Pallu R and Alam M S 2012 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. 49 324

    Article  CAS  Google Scholar 

  37. Haider S, Alam M S, Hamid H, Shafi S, Dhulap A, Hussain F, Alam P, Umar S, Pasha M A Q, Bano S, Nazreen S, Ali Y and Kharbanda C 2014 Synthesis of novel 2-mercaptobenzoxazole based 1,2,3-triazoles as inhibitors of proinflammatory cytokines and suppressors of COX-2 gene expression Eur. J. Med. Chem. 81 204

    Article  CAS  Google Scholar 

  38. Kaushik C P, Pahwa A, Singh D, Kumar K and Luxmi R 2019 Efficient synthesis, antitubercular and antimicrobial evaluation of 1, 4-disubstituted 1, 2, 3-triazoles with amide functionality Montash. Chem. 150 1127

    Article  CAS  Google Scholar 

Download references

Acknowledgement

Authors are highly thankful to the Council of Scientific and Industrial Research (CSIR), New Delhi, India.

Author information

Authors and Affiliations

  1. Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, Haryana, India

    C P Kaushik & Manisha Chahal

Authors
  1. C P Kaushik
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Manisha Chahal
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to C P Kaushik.

Ethics declarations

Conflicts of interest

No potential conflict of interest was reported by the authors.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 3.56 MB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kaushik, C.P., Chahal, M. Synthesis and antibacterial activity of benzothiazole and benzoxazole-appended substituted 1,2,3-triazoles. J Chem Sci 132, 142 (2020). https://doi.org/10.1007/s12039-020-01844-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s12039-020-01844-8

Keywords

Search

Navigation