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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The data that support the findings of this study are available from the corresponding author upon reasonable request.
REFERENCES
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
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
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
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
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
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
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
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
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
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
Zwanenburg, B., Pure Appl. Chem., 1999, vol. 71,pp. 423–430. https://doi.org/10.1002/chin.199952279
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
Chen, Y.W., Acta Anaesthesiol. Taiwan., 2010, vol. 48,pp. 3–7. https://www.sciencedirect.com/science/article/pii/S1875459710600021
Maurer, H. and Pfleger, K., Arch. Toxicol., 1988, vol. 62,pp. 185–191. https://doi.org/10.1007/BF00570138
Jarchovsky, J., Zamir, D., and Plavnik, L., Harefuah.,1991, vol. 121, pp. 435–436. https://pubmed.ncbi.nlm.nih.gov/38431863
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
Mallam, V., Allam, V., and Brahmeshwari, G., Russ. J. Bioorg. Chem., 2023, vol. 49, pp. 1381–1388. https://doi.org/10.1134/S1068162023060183
Kiselyuk, A., J. Biomol. Screen., 2010, vol. 15, pp. 663–670. https://doi.org/10.1177/1087057110372257
Motohashi, N., Kawase, M., Saito, S., and Sakagami, S., Curr. Drug. Targets, 2005, vol. 1, pp. 237–246. https://doi.org/10.2174/1389450003349191
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
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
Vasudha Mallam, Kumar, M.R., and Vijayakumar, B., Russ. J. Bioorg. Chem., 2022, vol. 48, pp. 596–600. https://doi.org/10.1134/S1068162022030219
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
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
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
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
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
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
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
Seah, I., Su, X., and Lingam, G., Eye, 2020, vol. 34,pp. 1155–1157. https://doi.org/10.1038/s41433-020-0790-7
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
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
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
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
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
Kadeer, M.D. and Ramesh, D., Asian J. Chem., 2024,vol. 36, pp. 628–634. https://doi.org/10.14233/ajchem.2024.30953
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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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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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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DOI: https://doi.org/10.1134/S1068162024030336