Skip to main content
SpringerLink
Log in

Synthesis of Benzothiazole and Pyrimidine Based Fused Derivatives and Their Biological Evaluation

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

In the present study a series of ethyl 4-(substituted)-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate and ethyl 4-(substituted)-8-methoxy-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate have been synthesized and evaluated for their preliminary antibacterial, antifungal, antimycobacterial, antioxidant and antimalarial activity. Among all the synthesized derivatives some of the compounds exists good biological activity which is similar to that of standard drugs. These facts make the compounds interesting candidates for further evaluation of their efficacy in the treatment microbial, tubercular and malarial disease.

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

Scheme

REFERENCES

  1. Tapkir, A., Chitlange, S.S., Bhole, R.P., and Patil, P.D., Thai. J. Pharm. Sci., 2023, vol. 45, p. 428.

    Google Scholar 

  2. Kumar, S. and Dubey, B., J. Drug. Deliv. Ther., 2022, vol. 12, p. 270. https://doi.org/10.22270/jddt.v12i4-S.5549

    Article  CAS  Google Scholar 

  3. Katharigatta, N.V., Med. Chem., 2019, vol. 15, p. 311. https://doi.org/10.2174/1573406414666180703121815

    Article  CAS  Google Scholar 

  4. Suresh, J., Lakshmi, S., Madhesh, K., Karunya, B., Noorulla, K.M., and Surya, P.R., Int. J. Pharm. Sci. Res., 2018, vol. 9, p. 563. https://doi.org/10.13040/IJPSR.0975-8232.9(2).563-74

    Article  CAS  Google Scholar 

  5. Mariappan, G., Prabhat, P., Lingadurai, S., Banerjee, J., Patangia, U., and Nath, S., J. Korean Chem. Soc., 2012, vol. 56, p. 251. https://doi.org/10.5012/jkcs.2012.56.2.251

    Article  CAS  Google Scholar 

  6. Meltzer-Mats, E., Babai-Shani, G., Pasternak, L., Uritsky, N., Getter, T., Viskind, O., Eckel, J., Cerasi, E., Senderowitz, H., Sasson, S., and Arie, G., J. Med. Chem., 2013, vol. 56, p. 5335. https://doi.org/10.1021/jm4001488

    Article  CAS  PubMed  Google Scholar 

  7. Pappachen, L., Zachariah, S., and Chandran, D., Asian J. Pharm. Clin. Res., 2017, vol. 10, p. 150. https://doi.org/10.22159/ajpcr.2017.v10i4.16407

    Article  CAS  Google Scholar 

  8. Kurt, H., Ayaz, L., Ayaz, F., Seferoglu, Z., and Nural, Y., Curr. Org. Synth., 2022, vol. 19, p. 772. https://doi.org/10.2174/1570179419666220330001036

    Article  CAS  PubMed  Google Scholar 

  9. Omar, M., Aboulwafa, O., Issa, D., El-Shoukrofy, M., Amr, M., and El-Ashmawy, I., Med. Chem. Commun., 2017, vol. 8, p.1440. https://doi.org/10.1039/C7MD00140A

    Article  CAS  Google Scholar 

  10. Haugwitz, R., Angel, R., Jacobs, G., Maurer, B., Narayanan, V., Cruthers, L., and Szanto, J., J. Med. Chem., 1982, vol. 25, p. 969. https://doi.org/10.1021/jm00147a019

    Article  CAS  PubMed  Google Scholar 

  11. Gupta, K., Sirbaiya, A.K., Kumar, V., Rahman, M.A., Mini-Rev. Med. Chem., 2022, vol. 22, p. 1895. https://doi.org/10.2174/1389557522666220217101805

    Article  CAS  PubMed  Google Scholar 

  12. Azzam, R., Elboshi, H., and Elgemeie, G., Antibiotics, 2022, vol. 11, p. 1799. https://doi.org/10.3390/antibiotics11121799

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Yu, F., Xu, Y., Wang, H., Chi, L., Si, X., Gao, C., Dai, H., Liu, L., Wang, Z., Ke, Y., Liu, H., and Zhang, Q., Med. Chem. Res., 2023, vol. 32, p. 2156. https://doi.org/10.1007/s00044-023-03117-8

    Article  CAS  Google Scholar 

  14. Azzam, R.A., Elboshi, H.A., and Elgemeie, G.H., ACS Omega, 2020, vol. 5, p. 30023. https://doi.org/10.1021/acsomega.0c04424

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Asiri, Y.I., Alsayari, A., Muhsinah, A.B., Mabkhot, Y.N., and Hassan, M.Z., J. Pharm. Pharmacol., 2020, vol. 72, p. 1459. https://doi.org/10.1111/jphp.13331

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Mei, W.-w., Ji, S.-s., Xiao, W., Wang, X.-d., Jiang, C.-s., Ma, W.-q., Zhang, H.-y., Gong, J.-x., and Guo, Y.-W., Monatsh. Fur. Chem., 2017, vol. 148, p. 1807. https://doi.org/10.1007/s00706-017-1993-x

    Article  CAS  Google Scholar 

  17. Ugwu, D.I., Okoro, U.C., Ukoha, P.O., Gupta, A., and Okafor, S.N., J. Enzyme Inhib. Med. Chem., 2018, vol. 33, p. 405. https://doi.org/10.1080/14756366.2018.1426573

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Zheng, X.J., Li, C.S., Cui, M.Y., Song, Z.W., Bai, X.Q., Liang, C.W., Wang, H.Y., and Zhang, T.Y., Bioorg. Med. Chem. Lett., 2020, vol. 30, p. 127237. https://doi.org/10.1016/j.bmcl.2020.127237

    Article  CAS  PubMed  Google Scholar 

  19. Cabrera-Pérez, L.C., Padilla-Martínez, I.I., Cruz, A., Mendieta-Wejebe, J.E., Tamay-Cach, F., and Rosales-Hernández, M.C., Arab. J. Chem., 2016, vol. 12, p. 3871. https://doi.org/10.1016/j.arabjc.2016.02.004

    Article  CAS  Google Scholar 

  20. Djuidje, E.N., Barbari, R., Baldisserotto, A., Durini, E., Sciabica, S., Balzarini, J., Liekens, S., Vertuani, S., and Manfredini, S., Antioxidants (Basel, Switzerland), 2022, vol. 11, p. 407. https://doi.org/10.3390/antiox11020407

    Article  CAS  PubMed  Google Scholar 

  21. Gagoria, J., Verma, P.K., and Khatkar, A., Cent. Nerv. Syst. Agents Med. Chem., 2015, p. 11. https://doi.org/10.2174/1871524915666150112094206

  22. Khokra, S.L., Arora, K., Khan, S.A., Kaushik, P., Saini, R., Husain, A., Iran. J. Pharm. Res., 2019, vol. 18, p. 1.

    CAS  PubMed  PubMed Central  Google Scholar 

  23. Liu, D.-C., Zhang, H.-J., Jin, C.-M., and Quan, Z.-S., Molecules, 2016, vol. 21, p. 164. https://doi.org/10.3390/molecules21030164

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. Morales-Garcia, J., Salado, I., Cristobal, M., Gil, C., PérezCastillo, A., Martinez, A., and Perez, D., ACS Omega, 2017, vol. 2, p. 5215. https://doi.org/10.1021/acsomega.7b00869

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Mahapatra, A., Prasad, T., and Sharma, T., Future J. Pharm. Sci., 2021, vol. 7, p. 123. https://doi.org/10.1186/s43094-021-00274-8

    Article  Google Scholar 

  26. Bhat, A.R., Dongre, R.S., Naikoo, G.A., Hassan, I.U., and Ara, T., J. Taibah. Univ. Sci., 2017, vol. 11, p. 1047. https://doi.org/10.1016/j.jtusci.2017.05.005

    Article  Google Scholar 

  27. Merugu, R., Garimella, S., Balla, D., and Sambaru, K., Int. J. Pharmtech. Res., 2015, vol. 8, p. 88. https://doi.org/10.1002/chin.201629252

    Article  CAS  Google Scholar 

  28. Wiegand, I., Hilpert, K., and Hancock, R., Nat. Protoc., 2008, vol. 3, p. 163. https://doi.org/10.1038/nprot.2007.521

    Article  CAS  PubMed  Google Scholar 

  29. Tsukatani, T., Suenaga, H., Shiga, M., Noguchi, K., Ishiyama, M., Ezoe, T., and Matsumoto, K., J. Microbiol. Methods, 2012, vol. 90, p. 160. https://doi.org/10.1016/j.mimet.2012.05.001

    Article  CAS  PubMed  Google Scholar 

  30. Isenberg, H.D., Clinical Microbiology Procedures Handbook. American Society of Microbiology, 1992.

  31. Desjardins, R.E., Canfield, C.J., Haynes, J.D., and Chulay, J.D., Antimicrob. Agents. Chemother., 1979, vol. 16, p. 710. https://doi.org/10.1128/AAC.16.6.710

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. Brand-Williams, W., Cuvelier, M.E., and Berset, C., LWT Food Sci. Technol., 1995, vol. 28, p. 25. https://doi.org/10.1016/S0023-6438(95)80008-5

    Article  CAS  Google Scholar 

Download references

Funding

The authors are thankful to Professor and Head, Department of Chemistry, VNSGU, Surat for providing necessary laboratory facilities and UGC-BSR faculty fellow [no. f.4-5(11)2019(BSR)] for financially supporting to the corresponding author. Microcare laboratory, Surat for biological activity, SAIF, Chandigarh for 1H and 13C NMR spectral analysis.

Author information

Authors and Affiliations

  1. Department of Chemistry, Veer Narmad South Gujarat University, 395007, Surat, India

    Navin B. Patel & Pratik N. Maisuria

  2. Department of Chemistry, The M.S. University of Baroda, 390002, Vadodara, India

    Akash V. Gujarati & Divyesh K. Patel

Authors
  1. Navin B. Patel
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Pratik N. Maisuria
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Akash V. Gujarati
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Divyesh K. Patel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Navin B. Patel.

Ethics declarations

The authors of this work declare that they have no conflicts of interest.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Patel, N.B., Maisuria, P.N., Gujarati, A.V. et al. Synthesis of Benzothiazole and Pyrimidine Based Fused Derivatives and Their Biological Evaluation. Russ J Org Chem 59 (Suppl 1), S140–S149 (2023). https://doi.org/10.1134/S1070428023130158

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428023130158

Keywords:

Search

Navigation