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Ultrasound Assisted Synthesis of Phenothiazine Based Chalcone Derivatives, Their Antibacterial Studies and Molecular Docking Against COVID-19 Virus Spike Protein Inhibitor

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Abstract

Objective: Phenothiazine and its derivatives have many biological effects, such as killing bacteria, protecting cells from damage, fighting cancer, and other drug-related effects. Methods: Phenothiazine-containing chalcone derivatives were tested for antibacterial activity using the agar-well diffusion method. For COVID-19, a molecular docking investigation of produced molecules was performed using AutoDock 2.0 software. Results and Discussion: Phenothiazine derivatives were characterized using spectral techniques such as IR, NMR, and mass spectral data. All the synthesized derivatives shown good antibacterial studies against various bacterial strains. The docking results of the synthesized ligand possesses good binding energy with 2AJF protein. Conclusions: This work presented standard procedures and focused on the synthesis and spectrum characterization of a series of phenothiazine integrated Chalcone derivatives employing ultrasonic irradiation. Phenothiazine and chalcone compounds have been shown to have potent antibacterial activity. The phenothiazine-based chalcone moieties in the drug’s formation of hydrogen bonds with the target enzyme make it an efficient antiviral agent, according to the docking finding.

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DATA AVAILABILITY

The data that support the findings of this study are available from the corresponding author upon reasonable request.

REFERENCES

  1. Młodawska, B.M., Pluta, K., Latocha, M., Jeleń, M.,Kuśmierz, D., Suwińska, K., Shkurenko, A., Czuba, Z.,and Jurzak, M., J. Enzyme Inhib. Med. Chem., 2019, vol. 34, pp. 1298–1306. https://doi.org/10.1080/14756366.2019.1639695

    Article  CAS  Google Scholar 

  2. Bajaj, S., Asati, V., Singh, J., and Roy, P.P., Eur. J. Med.Chem., 2015, vol. 97, pp. 124­–141. https://doi.org/10.1016/j.ejmech.2015.04.051

    Article  CAS  PubMed  Google Scholar 

  3. Yugandhar, D., Nayak, V.L., and Archana, S., Eur. J. Med. Chem., 2015, vol. 101, pp. 348–357. https://doi.org/10.1080/14756366.2019.1639695

    Article  CAS  PubMed  Google Scholar 

  4. Gupta, R.R. and Kumar, M., Chem. Phys. Lett., 1990,vol. 170, pp. 1–161. https://doi.org/10.1016/0009-2614(90)87101-V

  5. Luan, Y., Liu, J., Gao, J., and Wang, J., Lett. Drug. Des.Discov., 2020, vol. 17, pp. 57–67. https://doi.org/10.2174/1570180816666181115112236

    Article  CAS  Google Scholar 

  6. Jaszczyszyn, A., Gąsiorowski, K., Świątek, P., Malinka, W., Boczula, K.C., Petrus, J., and Matusewicz, B.C., Pharmacol. Rep., 2012, vol. 64, pp. 16–23. https://doi.org/10.1016/S1734-1140(12)70726-0

    Article  CAS  PubMed  Google Scholar 

  7. Pluta, K., Młodawska, B.M., and Jeleń, M., Eur. J. Med.Chem., 2011, vol. 46, pp. 3179–3189. https://doi.org/10.1016/j.ejmech.2011.05.013

    Article  CAS  PubMed  Google Scholar 

  8. Motohashi, N., Gollapudi, S.R., Emrani, J., and Bhattiprolu, K.R., Cancer Invest., 1991, vol. 9, pp. 305–319. https://doi.org/10.3109/07357909109021328

    Article  CAS  PubMed  Google Scholar 

  9. Darvesh, S., Pottie, I.R., Darvesh, K.V., McDonald, R.S., Walsh, R., Conrad, S., Penwell, A., Mataija, D., Martin E., Biol. Med. Chem., 2010, vol. 18,pp. 2232–2244. https://doi.org/10.1016/j.bmc.2010.01.066

  10. Ramar, S., Iniyaval, S., Padmavathy, K., Liew, H.S., Looi, C.K., Mai, C.W., and Ramalingan, C., New. J. Chem., 2019, vol. 43, pp. 17046–17057. https://doi.org/10.1039/C9NJ03394G

    Article  Google Scholar 

  11. Zwanenburg, B., Pure Appl. Chem., 1999, vol. 71,pp. 423–430. https://doi.org/10.1002/chin.199952279

  12. Varga, B., Csonka, A., Csonka, A., Molnár, M., Amaral, L., and Spengler, G., Anticancer Res., 2017,vol. 37, pp. 5983–5993. https://doi.org/10.21873/anticanres.12045

  13. Chen, Y.W., Acta Anaesthesiol. Taiwan., 2010, vol. 48,pp. 3–7. https://www.sciencedirect.com/science/article/pii/S1875459710600021

  14. Maurer, H. and Pfleger, K., Arch. Toxicol., 1988, vol. 62,pp. 185–191. https://doi.org/10.1007/BF00570138

  15. Jarchovsky, J., Zamir, D., and Plavnik, L., Harefuah.,1991, vol. 121, pp. 435–436. https://pubmed.ncbi.nlm.nih.gov/38431863

  16. Singh, G., Kumar, N., Yadav, A.K., and Mishra, A.K., Heteroat. Chem., 2003, vol. 14, pp. 481–486. https://doi.org/10.1002/hc.10165

    Article  CAS  Google Scholar 

  17. Mallam, V., Allam, V., and Brahmeshwari, G., Russ. J. Bioorg. Chem., 2023, vol. 49, pp. 1381–1388. https://doi.org/10.1134/S1068162023060183

    Article  CAS  Google Scholar 

  18. Kiselyuk, A., J. Biomol. Screen., 2010, vol. 15, pp. 663–670. https://doi.org/10.1177/1087057110372257

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Motohashi, N., Kawase, M., Saito, S., and Sakagami, S., Curr. Drug. Targets, 2005, vol. 1, pp. 237–246. https://doi.org/10.2174/1389450003349191

    Article  Google Scholar 

  20. Venkatesan, K., Satyanarayana, V.S.V., and Sivakumar, A., Polyc. Arom. Comp., 2023, vol. 43, pp. 850–859. https://doi.org/10.1080/10406638.2021.2021254

    Article  CAS  Google Scholar 

  21. Venkatesan, K., Satyanarayana, V.S.V., Sivakumar, A., Ramamurthy, C., and Thirunavukkarusu, C.,J. Heterocycl. Chem., 2020, vol. 57, pp. 2722–2728. https://doi.org/10.1002/jhet.3980

    Article  CAS  Google Scholar 

  22. Vasudha Mallam, Kumar, M.R., and Vijayakumar, B., Russ. J. Bioorg. Chem., 2022, vol. 48, pp. 596–600. https://doi.org/10.1134/S1068162022030219

    Article  CAS  Google Scholar 

  23. Venkatesan, K., Satyanarayana, V.S.V., Mohanapriya, K., Khora, S.S., and Sivakumar, A., Res. Chem. Intermed.,2015, vol. 41, pp. 595–607. https://doi.org/10.1007/s11164-013-1213-1

  24. Kumar, K., Kumar, G., and Shukla, I.C., SN Appl. Sci.,2020, vol. 2, p. 1241. https://doi.org/10.1007/s42452-020-3067-7

  25. Cheng, V.C., Lau, S.K., Woo, P.C., and Yuen, K.Y.,Clin. Microbiol. Rev., 2007, vol. 20, pp. 660–694. https://doi.org/10.1128/cmr.00023-07

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Lee, N., Hui, D., Wu, A., Chan, P., Cameron, P.,Joynt, G.M., Ahuja, A., Yung, M.Y., Leung, C.B., To, K.F.,Lui, S.F., Szeto, C.C., Chung, S., and Sung, J.J., N. Engl. J. Med., 2003, vol. 348, pp. 1986–1994. https://doi.org/10.1056/nejmoa030685

    Article  PubMed  Google Scholar 

  27. Zaki, A.M., Van Boheemen, S.M., Bestebroer, T.M., Osterhaus, A.D., and Fouchier, R.A., New Engl. J. Med., 2012, vol. 367, pp. 1814–1820. https://doi.org/10.1056/nejmoa1211721

    Article  CAS  PubMed  Google Scholar 

  28. De Groot, R.J., Baker, S.C., Baric, R.S., Brown, C.S.,Drosten, C., Enjuanes, L., Fouchier, R.A.M., Galiano, M.,Gorbalenya, A.E., Memish, Z.A., Perlman, S., Poon, L.L.M., Snijder, E.J., Stephens, G.M., Woo, P.C.Y., Zaki, A.M., Zambon, M., and Ziebuhr, J., J. Virol., 2013,vol. 87, pp. 7790–7792. https://doi.org/10.1128/jvi.01244-13

  29. Lee, P.R. and Hsueh, P.I., J. Microbiol. Immunol. Infect.,2020, vol. 53, pp. 365–367. https://doi.org/10.1016/j.jmii.2020.02.001

  30. Seah, I., Su, X., and Lingam, G., Eye, 2020, vol. 34,pp. 1155–1157. https://doi.org/10.1038/s41433-020-0790-7

  31. Venkateshan, M., Muthu, M., Suresh, J., and RanjithKumar R., J. Mol. Struct., 2020, vol. 1220, Article ID:128741. https://doi.org/10.1016/j.molstruc.2020.128741

  32. Swapna, P., Suryanarayana, B., and Ahmed, K.,Bioorg. Med. Chem. Lett., 2022, vol. 75, Article ID:128987. https://doi.org/10.1016/j.bmcl.2022.128987

  33. Pandya, K.M., Battula, S., and Kumar, K.A.A., Med. Chem. Res., 2023, vol. 32, pp. 1098–1108. https://doi.org/10.1007/s00044-023-03058-2

    Article  CAS  Google Scholar 

  34. Reshma, Hussain, Manohar, K., Mukesh, B., Ramana Reddy, B., Sravanthi, I., and Veerasomaiah, P., Asian J. Chem., 2023, vol. 35, pp. 2715–2725. https://doi.org/10.14233/ajchem.2023.27005

    Article  CAS  Google Scholar 

  35. Nandini, A.R., Ravindran, D.N.B., and Nattamai, B.,Bioorg. Chem., 2021, vol. 112, Article ID: 104967. https://doi.org/10.1016/j.bioorg.2021.104967

  36. Kadeer, M.D. and Ramesh, D., Asian J. Chem., 2024,vol. 36, pp. 628–634. https://doi.org/10.14233/ajchem.2024.30953

  37. Pasupathi, M., Rajarajan, M., Venkatesan, K., Arockiadoss, M., and Santhi, N., Polycycl. Aromat. Compd., 2024,vol. 44, pp. 1095–1108. https://doi.org/10.1080/10406638.2023.2186443

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This work was supported by regular institutional funding, and no additional grants were obtained.

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The authors NHB, TJD—contributed for preparation and characterization of compounds. The authors PVR, HS—contributed to manuscript preparation. The author MP for docking studies. The author KVS contributed to finalizing manuscript and done biological studies.

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Correspondence to K. Venkatesan.

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Venkatesan, K., Basha, N.H., Jagadish, T. et al. Ultrasound Assisted Synthesis of Phenothiazine Based Chalcone Derivatives, Their Antibacterial Studies and Molecular Docking Against COVID-19 Virus Spike Protein Inhibitor. Russ J Bioorg Chem 50, 1133–1140 (2024). https://doi.org/10.1134/S1068162024030336

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