Copyright (c) 2022 AJC
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Synthesis, Antimicrobial, Anthelmintic Activity, Enzymatic Degradation and Molecular Docking Studies of Some Azo Compounds containing Carvacrol Moiety
Corresponding Author(s) : S. Koshti
Asian Journal of Chemistry,
Vol. 34 No. 12 (2022): Vol 34 Issue 12, 2022
Abstract
In present work, the carvacrol was derivatized as azo compound by coupling method with eight different diazonium salts. The newly synthesized azo derivatives of carvacrol screened against four bacterial species and four fungal species and expressed in terms of zone of inhibition in mm and compared with standard. Furthermore, enzymatic degradation studies also been done by inoculating these newly synthesized azo derivatives with Pseudomonas aeruginosa bacterium species, which secretes the azoreductase enzyme as responsible for reduction of –N=N– linkage into two different primary aromatic amines, followed by anthelmintic activity and molecular docking study.
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- L. Marinelli, A. Di Stefano and I. Cacciatore, Phytochem. Rev., 17, 903 (2018); https://doi.org/10.1007/s11101-018-9569-x
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- E. Du, L. Gan, Z. Li, W. Wang, D. Liu and Y. Guo, J. Anim. Sci. Biotechnol., 6, 58 (2015); https://doi.org/10.1186/s40104-015-0055-7
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- S. Benkhaya, S. M’rabet and A. El Harfi, Heliyon, 6, e03271 (2020); https://doi.org/10.1016/j.heliyon.2020.e03271
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References
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I. Cacciatore, M. Di Giulio, E. Fornasari, A. Di Stefano, L.S. Cerasa, L. Marinelli, H. Turkez, E. Di Campli, S. Di Bartolomeo, I. Robuffo and L. Cellini, PLoS One, 10, e0120937 (2015); https://doi.org/10.1371/journal.pone.0120937
M. Friedman, J. Agric. Food Chem., 62, 7652 (2014); https://doi.org/10.1021/jf5023862
K. Zheng, S.-Z. Wu, Y.-W. Lv, P. Pang, L. Deng, H.-C. Xu, Y.-C. Shi and X.-Y. Chen, J. Ethnopharm., 268, 113555 (2021); https://doi.org/10.1016/j.jep.2020.113555
N. Didry, L. Dubreuil and M. Pinkas, Pharm. Acta Helv., 69, 25 (1994); https://doi.org/10.1016/0031-6865(94)90027-2
D.J. Son, Y.H. Park, Y.M. Kim, N.H. Chung and H.S. Lee, J. Microbiol. Biotechnol., 15, 425 (2005).
K. Can Baser, Curr. Pharm. Des., 14, 3106 (2008); https://doi.org/10.2174/138161208786404227
S. Mediouni, J.A. Jablonski, S. Tsuda, A. Barsamian, C. Kessing, A. Richard, A. Biswas, F. Toledo, V.M. Andrade, Y. Even, M. Stevenson, T. Tellinghuisen, H. Choe, M. Cameron, T.D. Bannister and S.T. Valente, J. Virol., 94, e00147-20 (2020); https://doi.org/10.1128/JVI.00147-20
M. Zotti, M. Colaianna, M. Morgese, P. Tucci, S. Schiavone, P. Avato and L. Trabace, Molecules, 18, 6161 (2013); https://doi.org/10.3390/molecules18066161
M. Almanaityte, J. Jurevicius and R. Macianskiene, Biomed. Res. Int., 2020, 6456805 (2020); https://doi.org/10.1155/2020/6456805
E. Du, L. Gan, Z. Li, W. Wang, D. Liu and Y. Guo, J. Anim. Sci. Biotechnol., 6, 58 (2015); https://doi.org/10.1186/s40104-015-0055-7
L. Wang, D. Wang, X. Wu, R. Xu and Y. Li, BMC Infect. Dis., 20, 832 (2020); https://doi.org/10.1186/s12879-020-05556-9
J.K.R. da Silva, P.L.B. Figueiredo, K.G. Byler and W.N. Setzer, Int. J. Mol. Sci., 21, 3426 (2020); https://doi.org/10.3390/ijms21103426
M. Asif, M. Saleem, M. Saadullah, H.S. Yaseen and R. Al Zarzour, Inflammopharmacol, 28, 1153 (2020); https://doi.org/10.1007/s10787-020-00744-0
D. Gilling, M. Kitajima, J. Torrey and K. Bright, J. Appl. Microbiol., 116, 1149 (2014); https://doi.org/10.1111/jam.12453
M. Mizielinska, P. Nawrotek, X. Stachurska, M. Ordon and A. Bartkowiak, Int. J. Mol. Sci., 22, 1717 (2021); https://doi.org/10.3390/ijms22041717
M.G. Seadawy, A.F. Gad, M.F. Elhoseny, B. El-Harty, M.D. Shamel, A.A. Elfiky, A. Ahmed and A.R.N. Zekri, Biomed. J. Scient. Tech. Res., 33, 26750 (2021); https://doi.org/10.26717/BJSTR.2021.34.005552
M.N. Khan, D.K. Parmar and D. Das, Mini Rev. Med. Chem., 21, 1071 (2021); https://doi.org/10.2174/1389557520999201123210025
S. Benkhaya, S. M’rabet and A. El Harfi, Heliyon, 6, e03271 (2020); https://doi.org/10.1016/j.heliyon.2020.e03271
J.-D. Tamokou, J. Tsemeugne, E.S. Fondjo, P. Sarkar, J.-R. Kuiate, A.N. Djintchui, B.L. Sondengam and P.K. Bag, Pharmacologia, 7, 182 (2016); https://doi.org/10.5567/pharmacologia.2016.182.192
Y. Ali, S.A. Hamid and U. Rashid, Mini Rev. Med. Chem., 18, 1548 (2018); https://doi.org/10.2174/1389557518666180524113111
C.B. Scarim and C.M. Chin, Eur. J. Med. Chem. Rep., 1, 100001 (2021); https://doi.org/10.1016/j.ejmcr.2021.100001
R. Walker, Food Cosmet. Toxicol., 8, 659 (1970); https://doi.org/10.1016/S0015-6264(70)80455-2
K.-T. Chung, S.E. Stevens and C.E. Cerniglia, Crit. Rev. Microbiol., 18, 175 (1992); https://doi.org/10.3109/10408419209114557
S. Liu, J. Ma and D. Zhao, Dyes Pigments, 75, 255 (2007); https://doi.org/10.1016/j.dyepig.2006.05.004
K. Peach and M.V. Tracy Modern Methods of Plant Analysis, vol. I, Springer-Verlag: Berlin (1956).
J. Moraes, A.A.L. Carvalho, E. Nakano, A.A.C. de Almeida, T.H.C. Marques, L.N. Andrade, R.M. de Freitas and D.P. de Sousa, Parasitol. Res., 112, 603 (2013); https://doi.org/10.1007/s00436-012-3172-7
J. Adu, C.D.K. Amengor, N. Mohammed Ibrahim, C. AmaningDanquah, C. Owusu Ansah, D.D. Gbadago and J. Sarpong-Agyapong, J. Trop. Med., 2020, 4850492 (2020); https://doi.org/10.1155/2020/4850492
A. Shaikh and J. Meshram, Cong. Chem., 1, 1 (2015); https://doi.org/10.1080/23312009.2015.1019809
A. Gbolade and A. Adeyemi, Fitoterapia, 79, 223 (2008); https://doi.org/10.1016/j.fitote.2007.11.023
O. Trott and A. Olson, J. Comput. Chem., 31, 455 (2010); https://doi.org/10.1002/JCC.21334