Skip to main content
SpringerLink
Log in

Synthesis and muscarinic acetylcholine receptor (mAChR) antagonist activity of substituted piperazine-triazoles

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

This study describes synthesis of a series of piperazine-triazole derivatives and their ex vivo evaluation for preliminary muscarinic acetylcholine receptor (mAChR) blocking activity on rat ileum model. A molecule based on benzonitrile piperazine triazole scaffold showed good tissue relaxation and blocking of neurotransmitter ACh in the ex vivo experiment.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Amenta F, Tayebati S (2007) Curr Med Chem 15:488

    Article  Google Scholar 

  2. Gilman A (1984) Cell 36:577

    Article  CAS  Google Scholar 

  3. Malbon C (2005) Nat Rev Mol Cell Biol 6:689

    Article  CAS  Google Scholar 

  4. Bonner T, Buckley N, Young A (1987) Science 237:527

    Article  CAS  Google Scholar 

  5. Barnes PJ (1989) Thorax 44:161

    Article  CAS  Google Scholar 

  6. Faulkner D, Fryer AD, MacLagan J (1986) Br J Pharmacol 88:181

    Article  CAS  Google Scholar 

  7. Dunn MA, Sidell FR (1989) JAMA 262:649

    Article  CAS  Google Scholar 

  8. Munro NB, Watson AP, Ambrose KR, Griffin GD (1990) Env Health Pers 89:205

    Article  CAS  Google Scholar 

  9. Acharya BN, Rao GBD, Kumar D, Kumar P, Kaushik MP (2015) Med Chem Res 24:1763

    Article  CAS  Google Scholar 

  10. Ghorpade RR, Kumar D, Nayak S, Acharya BN (2019) Monatsh Chem 150:1335

    Article  CAS  Google Scholar 

  11. Hulme EC, Birdsall NJM, Buckley NJ (1990) Annu Rev Pharmacol Toxicol 30:633

    Article  CAS  Google Scholar 

  12. Jin J, Budzik B, Wang Y, Shi D, Wang F, Xei H, Wan Z, Zhu C, Foley JJ, Webb EF, Berlanga M, Burman M, Sarau HM, Morrow DM, Moore ML, Rivero RA, Palovich M, Salmon M, Belmonte KE, Laine DI (2008) J Med Chem 51:5915

    Article  CAS  Google Scholar 

  13. Craig JC, Young RJ (1962) Org Synth 42:19

    Article  CAS  Google Scholar 

  14. Subashini K, Periandy S (2017) J Mol Str 1134:157

    Article  CAS  Google Scholar 

  15. Shelke N, Ghorpade RR, Pratap A, Tak V, Acharya BN (2015) RSC Adv 5:31226

    Article  CAS  Google Scholar 

  16. Gambacorti-Passerini C, Mologni L, Scapozza L, Bisson W, Goekjian P, D’Attoma J (2017) 2-Acylaminothiazole derivatives as ALK inhibitors and their preparation and use for the treatment of cancer. US Patent 9,708,279, July 18, 2017; (2015) Chem Abstr 162:176545

  17. Cottrell IF, Hand SD, Humphrey GR, Wright SHB (1991) J Heterocycl Chem 28:301

    Article  CAS  Google Scholar 

  18. Yadav D, Singh N, Kim TW, Kim JY, Park N-J, Baeg J-O (2019) Green Chem 21:2677

    Article  CAS  Google Scholar 

  19. Alvarez SG, Alvarez MT (1997) Synthesis 413

  20. Kolb HC, Finn MG, Sharpless BK (2001) Angew Chem Int Ed 40:2004

    Article  CAS  Google Scholar 

  21. Kruse CA, Hu J, Pan AC, Arlow DH, Rosenbaum DM, Rosemond E, Green HF, Liu Tong, Chae PS, Dror RO, Shae DE, Weis WI, Wess J, Kobilka BK (2012) Nature 482:552

  22. Haga K, Kruse AC, Asada H, Yurugi-Kobayashi T, Shiroishi M, Zhang C, Weis WI, Okada T, Kobilka BK, Haga T, Kobayashi T (2012) Nature 482:547

    Article  CAS  Google Scholar 

  23. Jain N, Kumar P, Kumar D, Mavai Y, Vijayaraghavan R (2012) Def Sci J 62:105

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This manuscript is assigned DRDE accession no. DRDE/SC/29/2020. We thank Director, DRDE, Gwalior for his keen interest and encouragement in the present work. The authors thank Ms Tara Yadav for characterizing the synthesized molecules.

Author information

Authors and Affiliations

  1. Defence R&D Establishment, Jhansi Road, Gwalior, India

    Badri Narayan Acharya, RamaRao Ghorpade, Kshetra Pal Singh & Deo Kumar

  2. Revenshaw University, Cuttack, Odisha, India

    Sabita Nayak

Authors
  1. Badri Narayan Acharya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. RamaRao Ghorpade
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kshetra Pal Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Deo Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sabita Nayak
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Badri Narayan Acharya.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file 1 (DOCX 6140 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Acharya, B.N., Ghorpade, R., Singh, K.P. et al. Synthesis and muscarinic acetylcholine receptor (mAChR) antagonist activity of substituted piperazine-triazoles. Monatsh Chem 152, 357–366 (2021). https://doi.org/10.1007/s00706-021-02752-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-021-02752-4

Keywords

Search

Navigation