Abstract
The new cyclohexenone derivatives have been synthesized by diazo-coupling reactions using 3,5-diphenylcyclohex-2-en-1-one (2) and hydrazone derivative 3 as versatile scaffolds. The structures of the newly synthesized compounds were smoothly elucidated based upon different spectral techniques. The new compounds which bearing azo, triazene or tetraazene moieties were evaluated as antioxidant and antimicrobial agents. The minimal inhibitory concentrations (MICs) values for the most active compounds in antibacterial activity were evaluated. Compounds 8 and 15 revealed the highest antioxidant activity with inhibition values (53.5%) and (47.8%), respectively. In the case of S. aureus, compound 10 exhibited potent antibacterial activity with (95.8%) AI. In the case of E. coli, compound 10 revealed excellent antibacterial activity with (84.6%) AI. In the case of C. albicans, compounds 10, 12 and 14 revealed the best activities with an activity index (66.7–74.1%).
Similar content being viewed by others
REFERENCES
Tretyakov, N.A., Dmitriev, M.V., and Maslivets, A.N., Russ. J. Org. Chem., 2021, vol. 57, p. 13. https://doi.org/10.1134/S1070428021010024
Bae, B.H., Im, K.S., Choi, W.C., Hong, J., Lee, C-O., Choi, J.S., Son, B.W., Song, J-I., and Jung, J.H., J. Nat. Prod., 2000, vol. 63, p. 1511. https://doi.org/10.1021/np0002076
Yamamoto, H. and Sham, J.H., J. Am. Chem. Soc., 1979, vol. 101, p. 1609. https://doi.org/10.1021/ja00500a049
Goeke, A., Mertl, D., and Brunner, G., Angew. Chem. Int. Ed., 2005, vol. 44, p. 99. https://doi.org/10.1002/anie.200461207
Yamashita, S., Iso, K., and Hirama, M., Org. Lett., 2008, vol. 10, p. 3413. https://doi.org/10.1021/ol8012099
Dyachenko, V.D., Sukach, S.M., and Morkovnik, A.S., Russ. J. Org. Chem., 2020, Vol. 56, p. 949. https://doi.org/10.1134/S1070428020060019
Shi, Z., Grohmann, C., and Glorius, F., Angew. Chem., Int. Ed., 2013, vol. 52, p. 5393. https://doi.org/10.1002/anie.201301426
Buffa, R., Sedova, P., Basarabova, I., Moravcova, M., Wolfova, L., Bobula, T., and Velebny, V., Carbohydr. Polym., 2015, vol. 134, p. 293. https://doi.org/10.1016/j.carbpol.2015.07.084
Hammuda, A., Shalaby, R., Rovida, S., Edmondson, D.E., Binda, C., and Khalil, A., Eur. J. Med. Chem., 2016, vol. 114, p. 162. https://doi.org/10.1016/j.ejmech.2016.02.038
Gouhar, R.S., Ewies, E.F., El-Shehry, M.F., Shaheen, M.N.F., and Ibrahim, E.-M.M.E., J. Heterocycl. Chem., 2018, vol. 55, p. 2368. https://doi.org/10.1002/jhet.3301
Green, O., Smith, N.A., Ellis, A.B., and Burstyn, J.N., J. Am. Chem. Soc., 2004, vol. 126, p. 5952. https://doi.org/10.1021/ja039203o
Hu, B., Liu, T.X., Zhang, P., Liu, Q., Bi, J., Shi, L., Zhang, Z., and Zhang, G., Org. Lett., 2018, vol. 20, p. 4801. https://doi.org/10.1021/acs.orglett.8b01956
Bianco, A., Cavarischia, C., and Guiso, M., Eur. J. Org. Chem., 2004, p. 2894. https://doi.org/10.1002/ejoc.200400032
Schroeder, M., Mathys, M., Ehrensperger, N., and Büchel, M., Chem. Biodiversity 2014, vol. 11, p. 1651. https://doi.org/10.1002/cbdv.201400072
Von Wangelin, A.J., Neumann, H., Gördes, D., Klaus, S., Strübing, D., and Beller, M., Chem. Eur. J., 2003, vol. 9, p. 4286. https://doi.org/10.1002/chem.200305048
Bag, S., Ghosh, S., Tulsan, R., Sood, A., Zhou, W., Schifone, C., Foster, M., LeVine, H., Török, B., and Török, M., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 2614. https://doi.org/10.1016/j.bmcl.2013.02.103
Reddy, L.V., Kumar, V., Sagar, R., and Shaw, A.K., Chem. Rev., 2013, vol. 113, p. 3605. https://doi.org/10.1021/cr200016m
Hu, L., Lu, X., and Deng, L., J. Am. Chem. Soc., 2015, vol. 137, p. 8400. https://doi.org/10.1021/jacs.5b05345
Breuer, M., Ditrich, K., Habicher, T., Kesseler, B., Hauer, M., Stürmer, R., and Zelinski, T., Angew. Chem., Int. Ed., 2004, vol. 43, p. 788. https://doi.org/10.1002/anie.200300599
Wu, S., Yang, N., Liu, Y., Cao, J., Hu, H., Sun, Y., and Liu, J., J. Polym. Sci., Part A: Polym. Chem., 2011, vol. 49, p. 293. https://doi.org/10.1002/pola.24452
Nazir, R., Meiling, T.T., Cywiński, P.J., and Gryko, D.T., Asian J. Org. Chem., 2015, vol. 4, p. 929. https://doi.org/10.1002/ajoc.201500242
Shin, S.Y., Park, J., Jung, Y., Lee, Y.H., Koh, D., Yoon, Y., and Lim, Y., Appl. Biol. Chem., 2020, vol. 63, p. 1. https://doi.org/10.1186/s13765-020-00567-1
Yaouba, S., Koch, A., Guantai, E.M., Derese, S., Irungu, B., Heydenreich, M., and Yenesew, A., Phytochem. Lett., 2018, vol. 23, p. 141. https://doi.org/10.1016/j.phytol.2017.12.001
Nesterkina, M., Barbalat, D., Konovalova, I., Shishkina, S., Atakay, M., Salih, B., and Kravchenko, I., Nat. Prod. Res., 2021, vol. 35, p. 4978. https://doi.org/10.1080/14786419.2020.1756804
Mousavi, S.R., Chirality, 2016, vol. 28, p. 728. https://doi.org/10.1002/chir.22653
Saranya, A.V. and Ravi, S., J. Pharm. Res., 2012, vol. 5, p. 1098. https://doi.org/10.1016/j.ejphar.2021.174091
Okoth, D.A., Akala, H.M., Johnson, J.D., and Koorbanally, N.A., Med. Chem. Res., 2016, vol. 25, p. 690. https://doi.org/10.1007/s00044-016-1521-2
Khan, J., Ali, G., Khan, R., Ullah, R., and Ullah, S., Neurol. Sci. 2019, vol. 40, p. 1799. https://doi.org/10.1007/s10072-019-03884-6
Ledoux, A., St-Gelais, A., Cieckiewicz, E., Jansen, O., Bordignon, A., Illien, B., Di Giovanni, N., Marvilliers, A., Hoareau, F., Pendeville, H., Leclercq, J.Q., and Frédérich, M., J. Nat. Prod., 2017, vol. 80, p. 1750. https://doi.org/10.1021/acs.jnatprod.6b01019
Monga, V., Goyal, K., Steindel, M., Malhotra, M., Rajani, D.P., and Rajani, S.D., Med. Chem. Res., 2014, vol. 23, p. 2019. https://doi.org/10.1007/s00044-013-0803-1
Kanagarajan, V., Ezhilarasi, M., Bhakiaraj, D., and Gopalakrishnan, M., Eur. Rev. Med. Pharmacol. Sci., 2013, vol. 17, p. 292. https://doi.org/10.1016/j.ejphar.2021.174091
Das, M. and Manna, K., Curr. Bioact. Compd., 2015, vol. 11, p. 239. https://doi.org/10.2174/157340721104151230104138
Nazar, M.F., Abdullah, M.I., Badshah, A., Mahmood, A., Rana, U.A., and Khan, S.U.-D., J. Mol. Struct., 2015, vol. 1086, p. 8. https://doi.org/10.1016/j.molstruc.2014.12.090
Mansour, S.Y., Sayed, G.H., Al-Halim, S.A., Marzouk, M.I., and Shaban, S.S., Russ. J. Org. Chem., 2020, vol. 56, p. 465. https://doi.org/10.1134/S1070428020030161
Okoth, D.A., and Koorbanally, N.A., Nat. Prod. Commun., 2015, vol. 10, p. 103. https://doi.org/10.1177/1934578X1501000126
Balasubramanian, Μ. and D’souza, A., Tetrahedron, 1968, vol. 24, p. 5399. https://doi.org/10.1016/S0040-4020(01)96334-3
Metwally, M.A., Abdel-Galil, E., Amer, F.A., and Abdallah, A.M., Am. J. Org. Chem., 2012, vol. 2, p. 28. https://doi.org/10.5923/J.AJOC.20120201.06
Afsah, E.M., Arab, A.M., and Abdel-Galil, E., Chemistry Select, 2019, vol. 4, p. 10649. https://doi.org/10.1002/slct.201901525
Howard, A.N. and Wild, F., Biochem. J., 1957, vol. 65, p. 651. https://doi.org/10.1042/bj0650651
Ahern, T.P. and Vaughan, K., J. Chem. Soc., Chem. Commun., 1973, p. 701. https://doi.org/10.1039/C39730000701
Chandrashekarachar, D., Chaitramallu, M., Rekha, N.D., Kesagudu, D., and Ranjini, P., Brit. J. Pharma. Res., 2016, vol. 11, p. 1. https://doi.org/10.9734/BJPR/2016/25645
Lissi, E.A., Modak, B., Torres, R., Escobar, J., and Urza, A., Free Radical Res., 1999, vol. 30, p. 471. https://doi.org/10.1080/10715769900300511
Refat, H.M. and Fadda, A.A., Eur. J. Med. Chem., 2013, vol. 70, p. 419. https://doi.org/10.1016/j.ejmech.2013.09.003
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Supplementary information
Rights and permissions
About this article
Cite this article
Abdel-Galil, E., Girges, M.M. & Said, G.E. Synthesis, Characterization, and Biological Evaluation of Novel Cyclohexenone Derivatives Incorporating Azo, Triazene, and Tetraazene Moieties. Russ J Gen Chem 92, 2169–2177 (2022). https://doi.org/10.1134/S1070363222100292
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363222100292