Abstract
An efficient ultrasound-promoted one-pot three-component synthesis of a series of new 1,2,3-triazole-linked tetrahydrobenzo[b]pyran derivatives as antifungal and antioxidant agents using NaHCO3 has been described for the first time. The bioassay result indicates that the compounds 7b, 7c, 7i and 7j displayed excellent antifungal activity with lower MIC = 12.5 µg/mL than the reference drug miconazole. Most of the compounds from the series showed promising antioxidant activity with lower IC50 values in the range 12.47 ± 0.60–16.49 ± 0.44 µg/mL in comparison with butylated hydroxy toluene (BHT). Molecular docking studies revealed that most of the newly synthesized compounds showed excellent binding affinity with the potential target sterol 14α-demethylase (CYP51). Moreover, in silico adsorption, distribution, metabolism and excretion (ADME) study shows that the derivatives may possess drug like properties for further development of newer therapeutic agents.
Graphic abstract
Similar content being viewed by others
References
Y. Wang, J. Xie, Y. Xing, L. Chen, Y. Li, T. Meng, W. Dong, X. Wang, Y. Dong, Antimicrob. Agents Chemother. 61, e00620-17 (2017)
C.Y. Low, C. Rotstein, F1000 Med. Rep. 3, 14 (2011)
M.K. Kathiravan, A.B. Salake, A.S. Chothe, P.B. Dudhe, R.P. Watode, M.S. Mukta, S. Gadhwe, Bioorg. Med. Chem. 20, 5678 (2012)
L. Scorzoni, A.C. de Paula, E. Silva, C.M. Marcos, P.A. Assato, W.C. de Melo, H.C. de Oliveira, C.B. Costa-Orlandi, M.J. Mendes-Giannini, A.M. Fusco-Almeida, Front. Microbiol. 8, 36 (2017)
V.T. Andriole, Int. J. Antimicrob. Agents 16, 317 (2000)
J. Beardsley, C.L. Halliday, S.C. Chen, T.C. Sorrell, Future Microbiol. 13, 1175 (2018)
T.Y. Hargrove, Z. Wawrzak, J. Liu, M.R. Waterman, W.D. Nes, G.I. Lepesheva, J. Lipid Res. 53, 311 (2012)
K. Xu, L. Huang, Z. Xu, Y. Wang, G. Bai, Q. Wu, X. Wang, S. Yu, Y. Jiang, Drug Des. Dev. Ther. 9, 1459 (2015)
R. Guezguez, K. Bougrin, K. El Akri, R. Benhida, Tetrahedron Lett. 47, 4807 (2006)
N.D. Thanh, D.S. Hai, N.T.T. Ha, D.T. Tung, C.T. Le, H.T.K. Van, V.N. Toan, D.N. Toan, L.H. Dang, Bioorg. Med. Chem. Lett. 29, 164 (2019)
F. Alonso, Y. Moglie, G. Radivoy, M. Yus, J. Org. Chem. 76, 8394 (2011)
S.G. Agalave, S.R. Mauja, V.S. Pore, Chem. Asian J. 6, 2696 (2011)
Z. Jiang, J. Gu, C. Wang, S. Wang, N. Liu, Y. Jiang, G. Dong, Y. Wang, Y. Liu, J. Yao, Z. Miao, W. Zhang, C. Sheng, Eur. J. Med. Chem. 82, 490 (2014)
C. Gill, G. Jadhav, M. Shaikh, R. Kale, A. Ghawalkar, D. Nagargoje, M. Shiradkar, Bioorg. Med. Chem. Lett. 18, 6244 (2008)
J. Mareddy, N. Suresh, C.G. Kumar, R. Kapavarapu, A. Jayasree, S. Pal, Bioorg. Med. Chem. Lett. 27, 518 (2017)
R. Pratap, V.J. Ram, Chem. Rev. 114, 10476 (2014)
D. Kumar, V.B. Reddy, S. Sharad, U. Dube, S. Kapur, Eur. J. Med. Chem. 44, 3805 (2009)
R.R. Kumar, S. Perumal, J.C. Menendez, Y. Perumal, D. Sriram, Bioorg. Med. Chem. 19, 3444 (2011)
A.M. Shestopalov, Y.M. Litvinov, L.A. Rodinovskaya, O.R. Malyshev, M.N. Semenova, V.V. Semeno, ACS Comb. Sci. 14, 484 (2012)
N.M. Sabry, H.M. Mohamed, E.S.A.E.H. Khattab, S.S. Motlaq, A.M. El-Agrody, Eur. J. Med. Chem. 46, 765 (2011)
B.F. Mirjalili, L. Zamani, K. Zomorodian, S. Khabnadideh, Z. Haghighijoo, Z. Malakotikhah, S.A.A. Mousavi, S. Khojasteh, J. Mol. Struct. 1116, 102 (2016)
W. Kemnitzer, J. Drewe, S. Jiang, H. Zhang, J. Zhao, C. Crogan-Grundy, L. Xu, S. Lamothe, H. Gourdeau, R. Denis, B. Tseng, S. Kasibhatla, S.X. Cai, J. Med. Chem. 50, 2858 (2007)
B.M. Chougala, S. Samundeeswari, M. Holiyachi, L.A. Shastri, S. Dodamani, S. Jalalpure, S.R. Dixit, S.D. Joshi, V.A. Sunagar, Eur. J. Med. Chem. 125, 101 (2017)
V.F. De Andrade-Neto, M.O. Goulart, J.F. Da Silva Filho, M.J. Da Silva, M.D.C. Pinto, A.V. Pinto, M.G. Zalis, L.H. Carvalho, A.U. Krettli, Bioorg. Med. Chem. Lett. 14, 1145 (2004)
N.D. Thanh, D.S. Hai, V.T.N. Bich, P.T.T. Hien, N.T.K. Duyen, N.T. Mai, T.T. Dung, V.N. Toan, H.T.K. Van, L.H. Dang, D.N. Toan, T.T.T. Van, Eur. J. Med. Chem. 167, 454 (2019)
F.N. Sadeh, M.T. Maghsoodlou, N. Hazeri, M. Kangani, Res. Chem. Intermed. 41, 5907 (2015)
J. Lu, X.W. Fu, G. Zhang, C. Wang, Res. Chem. Intermed. 42, 417 (2016)
I.A. Azath, P. Puthiaraj, K. Pitchumani, ACS Sustain. Chem. Eng. 1, 174 (2013)
H.R. Safaei, M. Shekouhy, S. Rahmanpur, A. Shirinfeshan, Green Chem. 14, 1696 (2012)
B. Amirheidari, M. Seifi, M. Abaszadeh, Res. Chem. Intermed. 42, 3413 (2016)
R.S. Bhosale, C.V. Magar, K.S. Solanke, S.B. Mane, S.S. Choudhary, R.P. Pawar, Synth. Commun. 37, 4353 (2007)
K.S. Pandit, P.V. Chavan, U.V. Desai, M.A. Kulkarni, P.P. Wadgaonkar, New J. Chem. 39, 4452 (2015)
H. Zhi, C. Lu, Q. Zhang, J. Luo, Chem. Commun. (2009). https://doi.org/10.1039/B822481A
J.A. Makawana, D.C. Mungra, M.P. Patel, R.G. Patel, Bioorg. Med. Chem. Lett. 21, 6166 (2011)
M. Esmaeilpour, J. Javidi, F. Dehghani, F.N. Dodeji, RSC Adv. 5, 26625 (2015)
M.G. Dekamin, M. Eslami, Green Chem. 16, 4914 (2014)
O.H. Qareaghaj, S. Mashkouri, M.R. Naimi-Jamal, G. Kaupp, RSC Adv. 4, 48191 (2014)
P. Anastas, N. Eghbali, Chem. Soc. Rev. 39, 301 (2010)
A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)
L. Levi, T.J.J. Muller, Chem. Soc. Rev. 45, 2825 (2016)
M.-O. Simon, C.-J. Li, Chem. Soc. Rev. 41, 1415 (2012)
G. Cravotto, P. Cintas, Chem. Soc. Rev. 35, 180 (2006)
M.H. Shaikh, D.D. Subhedar, L. Nawale, D. Sarkar, F.A.K. Khan, J.N. Sangshetti, B.B. Shingate, Med. Chem. Commun. 6, 1104 (2015)
D.D. Subhedar, M.H. Shaikh, B.B. Shingate, L. Nawale, D. Sarkar, V.M. Khedkar, Med. Chem. Commun. 7, 1832 (2016)
D.D. Subhedar, M.H. Shaikh, L. Nawale, D. Sarkar, V.M. Khedkar, B.B. Shingate, Bioorg. Med. Chem. Lett. 27, 922 (2017)
D.D. Subhedar, M.H. Shaikh, B.B. Shingate, L. Nawale, D. Sarkar, V.M. Khedkar, F.A.K. Khan, J.N. Sangshetti, Eur. J. Med. Chem. 125, 385 (2017)
C. Viegas-Junior, A. Danuello, V. da Silva Bolzani, E.J. Barreiro, C.A. Fraga, Curr. Med. Chem. 14, 1829 (2007)
C.H. Collins, Microbiological Methods, 4th edn. (Butterworth’s, London, 1976)
M. Burits, F. Bucar, Phytother. Res. 14, 323 (2000)
R.A. Friesner, R.B. Murphy, M.P. Repasky, L.L. Frye, J.R. Greenwood, T.A. Halgren, P.C. Sanschagrin, D.T. Mainz, J. Med. Chem. 49, 6177 (2006)
A.B. Danne, A.S. Choudhari, D. Sarkar, J.N. Sangshetti, V.M. Khedkar, B.B. Shingate, Res. Chem. Intermed. 44, 6283 (2018)
S.P. Khare, T.R. Deshmukh, J.N. Sangshetti, V.S. Krishna, D. Sriram, V.M. Khedkar, B.B. Shingate, Chem. Sel. 3, 13113 (2018)
A.B. Danne, A.S. Choudhari, S. Chakraborty, D. Sarkar, V.M. Khedkar, B.B. Shingate, Med. Chem. Commun. 9, 1114 (2018)
J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)
L. Ronchin, A. Vavasori, E. Amadio, G. Cavinato, L. Toniolo, J. Mol. Catal. A: Chem. 298, 23 (2009)
A. Mobinikhaledi, M.A.B. Fard, Acta Chim. Slov. 57, 931 (2010)
C. Kurumurthy, R.N. Kumar, T. Yakaiah, P.S. Rao, B. Narsaiah, Res. Chem. Intermed. 41, 3193 (2015)
R. Reddyrajula, U. Dalimba, S.M. Kumar, Eur. J. Med. Chem. 168, 263 (2019)
C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feeney, Adv. Drug Deliv. Rev. 46, 3 (2001)
Y.H. Zhao, M.H. Abraham, J. Le, A. Hersey, C.N. Luscombe, G. Beck, B. Sherborne, I. Cooper, Pharm. Res. 19, 1446 (2002)
Acknowledgements
One of the authors, S.P.K., is grateful to Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, for the award of university scholars fellowship. The authors are also thankful to the Head, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431 004, India, for providing the laboratory facility. The authors are also thankful to Schrodinger Inc. for providing the Schrodinger molecular modeling software for performing the molecular studies.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Khare, S.P., Deshmukh, T.R., Akolkar, S.V. et al. New 1,2,3-triazole-linked tetrahydrobenzo[b]pyran derivatives: Facile synthesis, biological evaluation and molecular docking study. Res Chem Intermed 45, 5159–5182 (2019). https://doi.org/10.1007/s11164-019-03906-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-019-03906-0