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Letters in Organic Chemistry

Author(s): Anjaneyulu Bendi* and Gullapalli Bhaskara Dharma Rao

DOI: 10.2174/1570178620666230111103902

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Strategic One-pot Synthesis of Glycosyl Annulated Phosphorylated/ Thiophosphorylated 1,2,3-Triazole Derivatives Using CuFe2O4 Nanoparticles as Heterogeneous Catalyst, their DFT and Molecular Docking Studies as Triazole Fungicides

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Abstract

In the present study, we have introduced an efficient solvent-free protocol for the synthesis of glycosyl annulated phosphorylated/thiophosphorylated 1,2,3-triazole derivatives using reusable CuFe2O4 magnetic nanoparticles as a heterogeneous catalyst with the protocols of popular click chemistry approach. Quantum chemical calculations of all the reactants and products have been calculated using density functional theory with Spartan-18 software. In addition, the molecular docking studies of all the glycosyl annulated phosphorylated/thiophosphorylated 1,2,3- triazole derivatives have been studied as effective fungicides against CaCYP51 (PDB ID 5EQB), protein of P. infestans effector target site (PDB ID: 2NAR), and SsCYP51(PDB code: 6CR2) using Autodock Vina and Discovery Studio software. Among the three different proteins, the binding energies of the compounds (5a-d) with CaCYP51 (PDB ID 5EQB) have shown better results in the range of 7.0 to 7.4 kcal/mol. Hence, these compounds may be used as strong fungicides for the inhibition of CaCYP51 (PDB ID 5EQB). In conclusion, the synthesized compounds may be better useful in agrochemical applications as vital fungicides.

Keywords: 1, 2, 3-triazoles, fungicides, CuFe2O4 nanoparticles, DFT method, molecular docking, tropiconazole.

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[1]
(a) Rostovtsev, V.V.; Green, L.G.; Fokin, V.V.; Sharpless, K.B. 2002, 41, 2596-2599.;
(b) Huisgen, R.; Szeimies, G.; Möbius, L. Chem. Ber., 1967, 100, 2494.
[2]
Bodine, K.D.; Gin, D.Y.; Gin, M.S. J. Am. Chem. Soc., 2004, 126(6), 1638-1639.
[http://dx.doi.org/10.1021/ja039374t] [PMID: 14871087]
[3]
(a) Smedley, C.J.; Li, G.; Barrow, A.S.; Gialelis, T.L.; Giel, M.C.; Ottonello, A.; Cheng, Y.; Kitamura, S.; Wolan, D.W.; Sharpless, K.B.; Moses, J.E. Angew. Chem. Int. Ed., 2020, 59(30), 12460-12469.
[http://dx.doi.org/10.1002/anie.202003219];
(b) Ganesh, V.; Sudhir, V.S.; Kundu, T.; Chandrasekaran, S. Chem. Asian J., 2011, 6(10), 2670-2694.
[http://dx.doi.org/10.1002/asia.201100408] [PMID: 21882351]
[4]
(a) Sabatini, J.J.; Johnson, E.C. ACS Omega, 2021, 6(18), 11813-11821.
[http://dx.doi.org/10.1021/acsomega.1c01115] [PMID: 34056335];
(b) Yang, J.; Wang, G.; Gong, X.; Zhang, J.; Wang, Y.A. ACS Omega, 2018, 3(8), 9739-9745.
[http://dx.doi.org/10.1021/acsomega.8b00614] [PMID: 31459103]
[5]
Bonandi, E.; Christodoulou, M.S.; Fumagalli, G.; Perdicchia, D.; Rastelli, G.; Passarella, D. Drug Discov. Today, 2017, 22(10), 1572-1581.
[http://dx.doi.org/10.1016/j.drudis.2017.05.014] [PMID: 28676407]
[6]
Sivakumar, K.; Xie, F.; Cash, B.M.; Long, S.; Barnhill, H.N.; Wang, Q. Org. Lett., 2004, 6(24), 4603-4606.
[http://dx.doi.org/10.1021/ol047955x] [PMID: 15548086]
[7]
dos Santos, J.A.; Reis Corrales, R.C.N.; Pavan, F.R.; Leite, C.; Queico, C.F.; de Paula Dias, R.M.; da Silva, A.D. Mediterr. J. Chem., 2012, 1, 282.
[http://dx.doi.org/10.13171/mjc.1.6.2012.02.05.15]
[8]
Löber, S.; Rodriguez-Loaiza, P.; Gmeiner, P. Org. Lett., 2003, 5(10), 1753-1755.
[http://dx.doi.org/10.1021/ol034520l] [PMID: 12735769]
[9]
(a) Boechat, N.; Ferreira, V.F.; Ferreira, S.B.; Ferreira, M.L.G.; da Silva, F.C.; Bastos, M.M.; Costa, M.S.; Lourenço, M.C.S.; Pinto, A.C.; Krettli, A.U.; Aguiar, A.C.; Teixeira, B.M.; da Silva, N.V.; Martins, P.R.C.; Bezerra, F.A.F.M.; Camilo, A.L.S.; da Silva, G.P.; Costa, C.C.P. J. Med. Chem., 2011, 54(17), 5988-5999.
[http://dx.doi.org/10.1021/jm2003624] [PMID: 21776985];
(b) Anjos, J.V.; Filho, R.A.W.N.; Nascimento, S.C.; Srivastava, R.M.; Melo, S.J.; Sinou, D. Eur. J. Med. Chem., 2009, 44, 3571-3576.
[http://dx.doi.org/10.1016/j.ejmech.2009.03.002] [PMID: 19345445];
(c) Kamal, A.; Shankaraiah, N.; Devaiah, V.; Laxma Reddy, K.; Juvekar, A.; Sen, S.; Kurian, N.; Zingde, S. Bioorg. Med. Chem. Lett., 2008, 18(4), 1468-1473.
[http://dx.doi.org/10.1016/j.bmcl.2007.12.063] [PMID: 18207392];
(d) Bakunov, S.A.; Bakunova, S.M.; Wenzler, T.; Ghebru, M.; Werbovetz, K.A.; Brun, R.; Tidwell, R.R. J. Med. Chem., 2010, 53(1), 254-272.
[http://dx.doi.org/10.1021/jm901178d] [PMID: 19928900]
[10]
(a) Aher, N.G.; Pore, V.S.; Mishra, N.N.; Kumar, A.; Shukla, P.K.; Sharma, A.; Bhat, M.K. Bioorg. Med. Chem. Lett., 2009, 19(3), 759-763.
[http://dx.doi.org/10.1016/j.bmcl.2008.12.026] [PMID: 19110424];
(b) Shichong, Y.; Xiaoyun, C.; Honggang, H.; Yongzheng, Y.; Zhongjun, G.; Yan, Z.; Qingyan, S.; Qiuye, W. Eur. J. Med. Chem., 2010, 45, 4435-4445.
[http://dx.doi.org/10.1016/j.ejmech.2010.07.002] [PMID: 20675019];
(c) Guantai, E.M.; Ncokazi, K.; Egan, T.J.; Gut, J.; Rosenthal, P.J.; Smith, P.J.; Chibale, K. Bioorg. Med. Chem., 2010, 18(23), 8243-8256.
[http://dx.doi.org/10.1016/j.bmc.2010.10.009];
(d) Silva, E.M., Jr; Barreto, R.F.S.M.; Pinto, M.C.F.R.; Silva, R.S.F.; Teixeira, D.V.; Souza, M.C.B.V.; Simone, C.A.; Castro, S.L.; Ferreira, V.F.; Pinto, A.V. Eur. J. Med. Chem., 2008, 43, 1774-1780.
[http://dx.doi.org/10.1016/j.ejmech.2007.10.015] [PMID: 18045742];
(e) Borgati, T.F.; Alves, R.B.; Teixeira, R.R.; Freitas, R.P.; Perdigão, T.G.; Silva, S.F.; Santos, A.A.; Bastidas, A.J.O. J. Braz. Chem. Soc., 2013, 24, 953-961.
[11]
Mao, M.Z.; Li, Y.X.; Zhou, Y.Y.; Chen, W.; Liu, T.W.; Yu, S.J.; Wang, S.H.; Li, Z.M. Chem. Biol. Drug Des., 2011, 78(4), 695-699.
[http://dx.doi.org/10.1111/j.1747-0285.2011.01172.x] [PMID: 21736703]
[12]
Gaur, M.; Goel, M.; Sridhar, L.; Ashok, T.D.S.; Prabhakar, S.; Dureja, P.; Raghunathan, P.; Eswaran, S.V. Monatsh. Chem., 2012, 143(2), 283-288.
[http://dx.doi.org/10.1007/s00706-011-0652-x]
[13]
Klopman, G.; Ptchelintsev, D. J. Comput. Aided Mol. Des., 1993, 7(3), 349-362.
[http://dx.doi.org/10.1007/BF00125508] [PMID: 8377029]
[14]
(a) Mares, D.; Romagnoli, C.; Andreotti, E.; Manfrini, M.; Vicentini, C.B. J. Agric. Food Chem., 2004, 52(7), 2003-2009.
[http://dx.doi.org/10.1021/jf030695y] [PMID: 15053543];
(b) Tripathi, R.P.; Yadav, A.K.; Ajay, A.; Bisht, S.S.; Chaturvedi, V.; Sinha, S.K. Eur. J. Med. Chem., 2010, 45, 142.
[http://dx.doi.org/10.1016/j.ejmech.2009.09.036] [PMID: 19846238]
[15]
Rozkiewicz, D.I.; Jańczewski, D.; Verboom, W.; Ravoo, B.J.; Reinhoudt, D.N. Angew. Chem. Int. Ed., 2006, 45(32), 5292-5296.
[http://dx.doi.org/10.1002/anie.200601090]
[16]
(a) Zinzalla, G.; Thurston, D.E. Future Med. Chem., 2009, 1(1), 65-93.
[http://dx.doi.org/10.4155/fmc.09.12] [PMID: 21426071];
(b) Neumann, D.M.; Cammarata, A.; Backes, G.; Palmer, G.E.; Jursic, B.S. Bioorg. Med. Chem., 2014, 22(2), 813-826.
[http://dx.doi.org/10.1016/j.bmc.2013.12.010] [PMID: 24361188]
[17]
(a) Kubacka, A.; Fernández-García, M.; Colón, G. Chem. Rev., 2012, 112(3), 1555-1614.
[http://dx.doi.org/10.1021/cr100454n] [PMID: 22107071];
(b) Casbeer, E.; Sharma, V.K.; Li, X.Z. Separ. Purif. Tech., 2012, 87, 1-14.
[http://dx.doi.org/10.1016/j.seppur.2011.11.034];
(c) Yang, H.; Yan, J.; Lu, Z.; Cheng, X.; Tang, Y. J. Alloys Compd., 2009, 476(1-2), 715-719.
[http://dx.doi.org/10.1016/j.jallcom.2008.09.104];
(d) Huang, W.; Zhu, J.; Zeng, H.Z.; Wei, X.H.; Zhang, Y.; Li, Y.R. Appl. Phys. Lett., 2006, 89, 2.;
(e) Fu, Y.; Xiong, P.; Chen, H.; Sun, X.; Wang, X. Ind. Eng. Chem. Res., 2012, 51(2), 725-731.
[http://dx.doi.org/10.1021/ie2026212]
[18]
(a) Ponhan, W.; Maensiri, S. Solid State Sci., 2009, 11(2), 479-484.
[http://dx.doi.org/10.1016/j.solidstatesciences.2008.06.019];
(b) Haihua, Y.; Jianhui, Y.; Zhouguang, L.; Xiang, C.; Yougen, T. J. Alloys Compd., 2009, 476, 715.;
(c) Huang, Z.; Zhu, Y.; Wang, S.; Yin, G. J. Alloys Compd., 2006, 6, 1931.;
(d) Lv, W.; Liu, B.; Luo, Z.K.; Ren, X.Z.; Zhang, P.Z. J. Alloys Compd., 2008, 465, 261.
[http://dx.doi.org/10.1016/j.jallcom.2007.10.049]
[19]
Nikolić V.N.; Vasić M.M.; Kisić. D. J. Solid State Chem., 2019, 275, 187-196.
[http://dx.doi.org/10.1016/j.jssc.2019.04.007]
[20]
Anjaneyulu, B.; Shalu, A.; Dharma Rao, G.B.; Jamshaiya, R.; Nutan, S. J. Chem., 2021, 7375058.
[21]
Dharma Rao, G.B.; Anjaneyulu, B.; Kaushik, M.P. RSC Advances, 2014, 4, 43321.
[http://dx.doi.org/10.1039/C4RA06587E]
[22]
Dharma Rao, G.B.; Anjaneyulu, B.; Kaushik, M.P. Tetrahedron Lett., 2014, 55(1), 19-22.
[http://dx.doi.org/10.1016/j.tetlet.2013.09.023]
[23]
Anjaneyulu, B.; Dharma Rao, G.B.; Nancy; Nagakalyan, S. J. Saudi Chem. Soc., 2021, 25, 101394.
[http://dx.doi.org/10.1016/j.jscs.2021.101394]
[24]
Adeboye, O. Arc. Org. Inorg. Chem. Sci., 2018, 1(5), 410-420.
[25]
Becke, A.D. J. Chem. Phys., 1993, 98(7), 5648-5652.
[http://dx.doi.org/10.1063/1.464913]
[26]
Lee, C.; Yang, W.; Parr, R.G. Phys. Rev., 1988, 37, 785-789.
[27]
Monk, B.C.; Tomasiak, T.M.; Keniya, M.V.; Huschmann, F.U.; Tyndall, J.D.A.; O’Connell, J.D., III; Cannon, R.D.; Finer-Morre, J.; Stroud, R.M. Proc. Natl. Acad. Sci., 2014, 111, 3865-3870.
[28]
Matena, A.; Bayer, P.; Zhukov, I.; Stanek, J.; Kozminski, W.; van West, P.; Wawra, S. 2018.
[29]
Friggeri, L.; Hargrove, T.Y.; Wawrzak, Z.; Lepesheva, G.I. Protein. Database, 2020.
[30]
Anjaneyulu, B.; Dharma Rao, G. B.; Nutan, S.; Ravi, T.; Lakhwinder, S. 2022, 7, e202103910.
[31]
Anjaneyulu, B.; Dharma Rao, G.B.; Bajaj, T. Results in Chemistry, 2021, 3, 100093.
[http://dx.doi.org/10.1016/j.rechem.2020.100093]
[32]
Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976.
[33]
(a) Zhang, G.; Musgrave, C.B. J. Phys. Chem. A, 2007, 111(8), 1554-1561.
[http://dx.doi.org/10.1021/jp061633o] [PMID: 17279730];
(b) DefonsiLestard. M.E.; Gil, D.M.; Estévez-Hernández, O.; Erben, M.F.; Duque. J. New J. Chem., 2015, 39, 7459-7747.;
(c) Lestard, M.E.D.; Gil, D.M.; Hernandez, O.E.; Erben, M.F.; Duque, J. New J. Chem., 2015, 39, 7459-7471.
[http://dx.doi.org/10.1039/C5NJ01210D]
[34]
Parr, R.G.; Szentpály, L.; Liu, S. J. Am. Chem. Soc., 1999, 121(9), 1922-1924.
[http://dx.doi.org/10.1021/ja983494x]
[35]
Chattraj, P.; Maiti, B.; Sarkar, U. J. Phys. Chem. A, 2003, 107, 4973-4975.
[http://dx.doi.org/10.1021/jp034707u]
[36]
Janak, J.F. Phys. Rev. B Condens. Matter, 1978, 18(12), 7165-7168.
[http://dx.doi.org/10.1103/PhysRevB.18.7165]
[37]
Perdew, J.P.; Parr, R.G.; Levy, M.; Balduz, J.L. Jr. Phys. Rev. Lett., 1982, 49(23), 1691-1694.
[http://dx.doi.org/10.1103/PhysRevLett.49.1691]
[38]
Koopmans, T. Physica, 1934, 1(1-6), 104-113.
[http://dx.doi.org/10.1016/S0031-8914(34)90011-2]
[39]
Gómez, B.; Likhanova, N.V.; Domínguez-Aguilar, M.A.; Martínez-Palou, R.; Vela, A.; Gázquez, J.L. J. Phys. Chem. B, 2006, 110(18), 8928-8934.
[http://dx.doi.org/10.1021/jp057143y] [PMID: 16671697]
[40]
Luque, F.J.; López, J.M.; Orozco, M. Theor. Chem. Acc., 2000, 103(3-4), 343-345.
[http://dx.doi.org/10.1007/s002149900013]
[41]
Okulik, N.; Jubert, A.H. J. Mol. Struct., 2004, 682(1-3), 55-62.
[http://dx.doi.org/10.1016/j.theochem.2004.04.069]
[42]
Trott, O.; Olson, A.J. J. Comput. Chem., 2010, 31(2), 455-461.
[PMID: 19499576]
[43]
Morris, G.M.; Huey, R.; Lindstrom, W.; Sanner, M.F.; Belew, R.K.; Goodsell, D.S.; Olson, A.J. J. Comput. Chem., 2009, 30(16), 2785-2791.
[http://dx.doi.org/10.1002/jcc.21256] [PMID: 19399780]