Abstract
Objective: To synthesize new dihydropyrazolo[1,5-a]pyrimidine derivatives and screen for the antibacterial and antifungal screening. Methods: We have synthesized a new series of 7-(1,3-diphenyl-1-H-pyrazol4-yl)-2-(methylthio)-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile compounds and screened compounds for antibacterial and antifungal activity. Gram-positive (Bacillus megaterium, Micrococcus spp.) and Gram-negative bacteria were tested for antibacterial activity (E.coli, S. typhi). Antifungal activity was tested on Ganoderma spp., A. niger, A. flavus, and Penicillium spp. Results: Some compounds have shown significant antimicrobial activity. Discussion: As per the results the compound possesses good biological activity due to presence of core pyrazolo[1,5-a]pyrimidine moiety. Conclusions: The synthesis of new 7-(1,3-diphenyl-1-Hpyrazol-4-yl)-2-(methylthio)-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile compounds was successfully completed and characterized by relevant techniques. Compounds are screened for the biological activities with moderate to good results. The MIC of the synthesized compound is compared to marketed available standard drugs.
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The data that support the findings of this study are available from the corresponding author upon reasonable request.
REFERENCES
Dubal, G.G., Vachchharajani, P.R., Solanki, M.J., and Shah, V.H., Russ. J. Gen. Chem., 2022, vol. 92, pp. 2161–2168. https://doi.org/10.1134/S1070363222100280
Lalpara, J.N., Vachhani, M.D., Hadiyal, S.D., Goswami, S., and Dubal, G.G., Russ. J. Org. Chem, 2021, vol. 57, pp. 241–246. https://doi.org/10.1134/S1070428021020159
Mahida, A., Joshi, K., Pandya, H. Rathod, J., and Dubal, G.G., Russ. J. Gen. Chem, 2023, vol. 93, pp. 1547–1559. https://doi.org/10.1134/S1070363223060270
Radia, A.J., Lalpara, J.N., Modasiya, I.J., and Dubal, G.G., J. Het. Chem., 2020, vol. 58, pp. 612–621. https://doi.org/10.1002/jhet.4200
Pansuriya, K., Lalpara, J.N., Hadiyal, S.D., Dhaduk, B.B., and Dubal, G.G., Chem. Data Collect., 2022, vol. 42, p. 100946. https://doi.org/10.1016/j.cdc.2022.100946
Pansuriya, K., Lalpara, J.N., Hadiyal, S.D., Dhaduk, B.B., and Dubal, G.G., Chem. Data Collect., 2022, vol. 41, p.100904. https://doi.org/10.1016/j.cdc.2022.100904
Vachhani, M.D., Lalpara, J.N., Hadiyal, S.D., and Dubal, G.G., Russ. J. Org. Chem., 2022, vol. 58, pp. 356–362. https://doi.org/10.1134/S1070428022030137
Trivedi, H.D., Patel, B.Y., Patel, P.K., and Sagar, S.R., Chem. Data Collect., 2022, vol. 41, p. 100923, https://doi.org/10.1016/j.cdc.2022.100923
Patel, A.S., Tala, S.D., Nariya, P.B., Ladva, K.D., and Kapuriya, N.P., J. Chin. Chem. Soc., 2019, vol. 66, pp. 247–252. https://doi.org/10.1002/jccs.201800203
Talpara, P.K., Dubal, G.G., and Shah, V.H., Int. Lett. Chem. Phys. Astro., 2017, vol. 74, pp. 9–14. https://doi.org/10.18052/www.scipress.com/ILCPA.74.9
Cetin, A. and Bildirici, I., J. Saudi Chem. Soc., 2018, vol. 22, pp. 279–296.
Harikrishna, N., Arun, M., Isloor, A.M., Ananda, K., Obaid, A., and Fun, H.K. New J. Chem., 2016, vol. 40, pp. 73–76.
Ardiansah, B., Asian J. Pharm. Clin. Res., 2018, vol. 11, pp. 88–94.
Metwally, N.H., Ragab, E.A., and Mohamed, M.S., J. Heterocycl. Chem., 2020, vol. 57, pp. 1698–1713.
Whitt, J., Duke, C., Ali, M.A., Chambers, S.A., Khan, M.M.K., Gilmore, D., and Alam, M.A., ACS Omega, 2019, vol. 4, pp. 14284–14293.
Al-Azmi, A., Mahmoud, H. ACS Omega, 2020, vol. 5, pp. 10160–10166
Zalaru, C., Dumitrascu, F., Draghici, C., Tarcomnicu, I., Tatia, R., Moldovan, L., Chifiriuc, M.C., Lazar, V., Marinescu, M., Nitulescu, M.G., and Ferbinteanu, M., J. Mol. Struct., 2018, vol. 1156, pp. 12–21. https://doi.org/10.1016/j.molstruc.2017.11.073
Saleh, I., KC, H.R., Roy, S., Abugazleh, M.K., Ali, H., Gilmoreb, D., and Alam, M.A., RSC Med. Chem., 2021, vol. 12, pp. 1690–1697. https://doi.org/10.1039/D1MD00230A
Marinescu, M., Antibiotics, 2021, vol. 10, p. 1002. https://doi.org/10.3390/antibiotics10081002
Kapadiya, K., Kavadia, K., Manvar, P., and Khunt, R., Anti-Infect. Agents, 2015, vol. 13, pp. 129–138.
Abdel Reheim, M.A.M. and Baker, S.M. Chem. Central J., 2017, vol. 11, p. 112. https://doi.org/10.1186/s13065-017-0339-4
Dubal, G.G., Vachchharajani, P.R., Solanki, M.J., and Shah, V.H., Russ. J. Gen. Chem., 2022, vol. 92, pp. 2734–2739. https://doi.org/10.1134/S1070363222120234
Sun, D., Babar Shahzad, M., Li, M., Wang, G., and Xu, D., Mater. Technol., 2015, vol. 30, pp. B90–B95. https://doi.org/10.1179/1753555714Y.0000000239
Brochot, A., Guilbot, A., Haddioui, L., and Roques, C., Microbiologyopen, 2017, vol. 6, p. e00459.
Al-Adham, I., Haddadin, R., and Collier, P., Pract. Disinfect. Preserv. Steriliz, 2013, vol. 5, p. 47.
Sokmen, A., Gulluce, M., Akpulat, H.A., Daferera, D., Tepe, B., Polissiou, M., Sokmen, M., and Sahin, F., Food Control, 2004, vol. 15, pp. 627–634. https://doi.org/10.1016/j.foodcont.2003.10.005
ACKNOWLEDGMENTS
The authors thank the Department of Chemistry, Government Science College, Fort-Songadh, India, Department of Chemistry, D.K..V Arts and Science College, Jamnagar, India, and Department of Chemistry, School of Science, R.K. University, Rajkot, India. for providing laboratory and other necessary facilities.
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The authors KAJ, HBP, and AKM participated in the synthesis, purification, and analysis of the data of the synthesized compound; the author and author IJM carried out the anti-microbial evaluation and prepared analysis of the activity data while author GGD organized data and written manuscript and handled all over the organization of work and guided for the target work to other.
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Joshi, K.A., Pandya, H.B., Mahida, A.K. et al. Synthesis and Antimicrobial Activity of New Dihydropyrazolo[1,5-a]pyrimidine Derivatives. Russ J Bioorg Chem 50, 304–312 (2024). https://doi.org/10.1134/S1068162024020134
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DOI: https://doi.org/10.1134/S1068162024020134