Copyright (c) 2024 Dr Deepak Wadhwa, Jyoti, Suman Devi, Dr Vikram Kumar
This work is licensed under a Creative Commons Attribution 4.0 International License.
Design, Development and Molecular Docking Studies of C-2 Sulfenylated Benzofurans: Potential Interleukin 1-β Antagonist
Corresponding Author(s) : Deepak Wadhwa
Asian Journal of Chemistry,
Vol. 36 No. 4 (2024): Vol 36 Issue 4, 2024
Abstract
An environmental friendly methodology for C-2 sulfenylation of benzofurans through dehydrogenative cross-coupling has been developed. Sulfenylation at second position is carried out using commercially available thiols in presence of molecular iodine and DMSO. The reaction accommodates wide spectrum of electronically diverse substituents on thiophenol ring. This process offers diverse advantages, including greener reaction conditions, moderate to good percentage yields, easy workup, no additional metal catalysts requirement and gram scale synthesis. Molecular docking studies is also conducted to substantiate interleukin 1-β antagonist nature of the designed compounds.
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Y.H. Miao, Y.H. Hu, J. Yang, T. Liu, J. Sun and X.J. Wang, RSC Adv., 9, 27510 (2019); https://doi.org/10.1039/C9RA04917G
K. Chand, Rajeshwari, A. Hiremathad, M. Singh, M.A. Santos and R.S. Keri, Pharmacol. Rep., 69, 281 (2017); https://doi.org/10.1016/j.pharep.2016.11.007
Z. Xu, S. Zhao, Z. Lv, L. Feng, Y. Wang, F. Zhang, L. Bai and J. Deng, Eur. J. Med. Chem., 162, 266 (2019); https://doi.org/10.1016/j.ejmech.2018.11.025
P.T. Thuy, N.V. Trang, D.X. Duc and N.T. Son, Struct. Chem., 32, 2271 (2021); https://doi.org/10.1007/s11224-021-01802-1
M. Thévenin, S. Thoret, P. Grellier and J. Dubois, Bioorg. Med. Chem., 21, 4885 (2013); https://doi.org/10.1016/j.bmc.2013.07.002
S. Rizzo, C. Rivière, L. Piazzi, A. Bisi, S. Gobbi, M. Bartolini, V. Andrisano, F. Morroni, A. Tarozzi, J.P. Monti and A. Rampa, J. Med. Chem., 51, 2883 (2008); https://doi.org/10.1021/jm8002747
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A. Higashi, N. Kishikawa, K. Ohyama and N. Kuroda, Tetrahedron Lett., 58, 2774 (2017); https://doi.org/10.1016/j.tetlet.2017.06.005
Y. Wang, X. Hou, C. Liu, M. Lei, Q. Zhou, S. Hu and Z. Xu, Inorg. Chem. Commun., 101, 135 (2019); https://doi.org/10.1016/j.inoche.2019.01.026
P. Proksch and E. Rodriguez, Phytochemistry, 22, 2335 (1983); https://doi.org/10.1016/0031-9422(83)80118-6
V. Sunitha, A.K. Kumar, B. Shankar, A.A. Kumar, T.M. Krishna, C.A. Lincoln and J. Pochampalli, Russ. J. Gen. Chem., 87, 322 (2017); https://doi.org/10.1134/S1070363217020281
Z. Liang, H. Xu, Y. Tian, M. Guo, X. Su and C. Guo, Molecules, 21, 732 (2016); https://doi.org/10.3390/molecules21060732
R. Kenchappa, Y.D. Bodke, S. Telkar and M.A. Sindhe, J. Chem. Biol., 10, 11 (2017); https://doi.org/10.1007/s12154-016-0160-x
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C. Wang, Y. Fan, Y. Yao, W. Chen, X. Cui, G. Zhu, W. Zhou and L. Tang, ChemistrySelect, 3, 29 (2018); https://doi.org/10.1002/slct.201702142
J.L. Farmer, M. Pompeo, A.J. Lough and M.G. Organ, Chem. Eur. J., 20, 15790 (2014); https://doi.org/10.1002/chem.201404705
S. Vásquez-Céspedes, A. Ferry, L. Candish and F. Glorius, Angew. Chem. Int. Ed., 54, 5772 (2015); https://doi.org/10.1002/anie.201411997
Q. Zhen, D. Huang, Y. Shao, T. Cheng and J. Chen, Org. Biomol. Chem., 16, 9204 (2018); https://doi.org/10.1039/C8OB02680G
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