Copyright (c) 2024 Jyotindra Mahyavanshi
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Structural Determination, Docking Study and Bioactivity of Novel Thiophene Derivatives
Corresponding Author(s) : Jyotindra Mahyavanshi
Asian Journal of Chemistry,
Vol. 36 No. 6 (2024): Vol 36 Issue 6, 2024
Abstract
The present study reveals 4-methyl-3-(propylamino)thiophene-2-carboxylic acid (Articaine acid) as precursor derivative to synthesize novel thiophene compounds to evaluate their biological activity. The synthesized compounds were subjected to comprehensive characterization techniques including mass spectra, NMR and IR spectroscopy, confirming their structural integrity. Their antimicrobial activity was assessed via minimum inhibitory concentration (MIC) assay against selected bacterial strains. The results emphasize the potential therapeutic applications of these thiophene analogues as efficacious antimicrobial agents, thereby encouraging further investigation. Molecular docking was used to examine thiophene derivative binding affinities on the S. aureus tyrosyl-tRNA synthetase protein and it was found that phenylethylamine derivatives had the highest binding affinity, followed by cyclohexyl methyl and benzylamine derivatives.
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- Y.N. Mabkhot, F. Alatibi, N.N. El-Sayed, S. Al-Showiman, N. Kheder, A. Wadood, A. Rauf, S. Bawazeer and T. Hadda, Molecules, 21, 222 (2016); https://doi.org/10.3390/molecules21020222
- F.S. Mehdhar, E. Abdel-Galil, A. Saeed, E. Abdel-Latif and G.E. Abd El Ghani, Polycycl. Aromat. Compd., 43, 4496 (2023); https://doi.org/10.1080/10406638.2022.2092518
- R.S. Keri, K. Chand, S. Budagumpi, S. Balappa Somappa, S.A. Patil and B.M. Nagaraja, Eur. J. Med. Chem., 138, 1002 (2017); https://doi.org/10.1016/j.ejmech.2017.07.038
- P.N. Sable, S. Ganguly and P.D. Chaudhari, Chin. Chem. Lett., 25, 1099 (2014); https://doi.org/10.1016/j.cclet.2014.03.044
- M. Rani and Y. Mohamad, J. Saudi Chem. Soc., 18, 411 (2014); https://doi.org/10.1016/j.jscs.2011.09.002
- R. Mishra, N. Sachan, N. Kumar, I. Mishra and P. Chand, J. Heterocycl. Chem., 55, 2019 (2018); https://doi.org/10.1002/jhet.3249
- C.D. Ba¢diceanu, Farmacia, 66, 553 (2018); https://doi.org/10.31925/farmacia.2018.3.24
- S. Deka, S. Mohan, J. Saravanan, M. Kakati, A. Talukdar, B.J. Sahariah, B.K. Dey and R.K. Sarma, Maced. J. Med. Sci., 5, 159 (2012).
- S. Pathania, R.K. Narang and R.K. Rawal, Eur. J. Med. Chem., 180, 486 (2019); https://doi.org/10.1016/j.ejmech.2019.07.043
- S. Lahsasni, D.A.M. Al-Hemyari, H.A. Ghabbour, Y.N. Mabkhoot, F.S. Aleanizy, A.A. Alothman and Z.M. Almarhoon, J. Chem., 2018, 8536063 (2018); https://doi.org/10.1155/2018/8536063
- M.A. El-Borai, H.F. Rizk, S.A. Ibrahim and A.K. Fares, J. Heterocycl. Chem., 56, 2787 (2019); https://doi.org/10.1002/jhet.3658
- H.M. Metwally, N.A. Khalaf, E. Abdel-Latif and M.A. Ismail, BMC Chem., 17, 6 (2023); https://doi.org/10.1186/s13065-023-00917-2
- Y.N. Mabkhot, N.A. Kaal, S. Alterary, M.S. Mubarak, A. Alsayari and A. Bin Muhsinah, J. Heterocycl. Chem., 56, 2845 (2019); https://doi.org/10.1002/jhet.3688
- I. Montenegro, E. Sánchez, E. Werner, P. Godoy, Y. Olguín, N. Caro, N. Ehrenfeld and A. Madrid, BMC Chem., 13, 1 (2019); https://doi.org/10.1186/s13065-019-0516-8
- A. Alsayari, A. Bin Muhsinah, Y.I. Asiri, K. Venkatesan and Y.N. Mabkhot, Polycycl. Aromat. Compd., 42, 6720 (2022); https://doi.org/10.1080/10406638.2021.1988998
- A.U. Isakhanyan, N.Z. Akopyan, G.M. Stepanyan, A.G. Arakelyan, Z.M. Buniatyan, R.E. Muradyan, G.A. Panosyan and A.A. Harutyunyan, Russ. J. Gen. Chem., 92, 2465 (2022); https://doi.org/10.1134/S1070363222110317
- Y.N. Mabkhot, N.A. Kaal, S. Alterary, S.S. Al-Showiman, T.A. Farghaly and M.S. Mubarak, Chem. Cent. J., 11, 75 (2017); https://doi.org/10.1186/s13065-017-0307-z
- K.C. prasad, B.N. Angothu, T.M. Latha and M. Nagulu, Int. J. Pharm. Biol. Sci., 7, 1 (2017); https://doi.org/10.21276/ijpbs.2017.7.1.1
- E. Abdel-Latif, E.M. Keshk, A.G.M. Khalil, A. Saeed and H.M. Metwally, J. Iran. Chem. Soc., 16, 629 (2019); https://doi.org/10.1007/s13738-018-1540-7
- S. Bondock, W. Fadaly and M.A. Metwally, Eur. J. Med. Chem., 45, 3692 (2010); https://doi.org/10.1016/j.ejmech.2010.05.018
- N.G. Heatley, Biochem. J., 38, 61 (1944); https://doi.org/10.1042/bj0380061
References
Y.N. Mabkhot, F. Alatibi, N.N. El-Sayed, S. Al-Showiman, N. Kheder, A. Wadood, A. Rauf, S. Bawazeer and T. Hadda, Molecules, 21, 222 (2016); https://doi.org/10.3390/molecules21020222
F.S. Mehdhar, E. Abdel-Galil, A. Saeed, E. Abdel-Latif and G.E. Abd El Ghani, Polycycl. Aromat. Compd., 43, 4496 (2023); https://doi.org/10.1080/10406638.2022.2092518
R.S. Keri, K. Chand, S. Budagumpi, S. Balappa Somappa, S.A. Patil and B.M. Nagaraja, Eur. J. Med. Chem., 138, 1002 (2017); https://doi.org/10.1016/j.ejmech.2017.07.038
P.N. Sable, S. Ganguly and P.D. Chaudhari, Chin. Chem. Lett., 25, 1099 (2014); https://doi.org/10.1016/j.cclet.2014.03.044
M. Rani and Y. Mohamad, J. Saudi Chem. Soc., 18, 411 (2014); https://doi.org/10.1016/j.jscs.2011.09.002
R. Mishra, N. Sachan, N. Kumar, I. Mishra and P. Chand, J. Heterocycl. Chem., 55, 2019 (2018); https://doi.org/10.1002/jhet.3249
C.D. Ba¢diceanu, Farmacia, 66, 553 (2018); https://doi.org/10.31925/farmacia.2018.3.24
S. Deka, S. Mohan, J. Saravanan, M. Kakati, A. Talukdar, B.J. Sahariah, B.K. Dey and R.K. Sarma, Maced. J. Med. Sci., 5, 159 (2012).
S. Pathania, R.K. Narang and R.K. Rawal, Eur. J. Med. Chem., 180, 486 (2019); https://doi.org/10.1016/j.ejmech.2019.07.043
S. Lahsasni, D.A.M. Al-Hemyari, H.A. Ghabbour, Y.N. Mabkhoot, F.S. Aleanizy, A.A. Alothman and Z.M. Almarhoon, J. Chem., 2018, 8536063 (2018); https://doi.org/10.1155/2018/8536063
M.A. El-Borai, H.F. Rizk, S.A. Ibrahim and A.K. Fares, J. Heterocycl. Chem., 56, 2787 (2019); https://doi.org/10.1002/jhet.3658
H.M. Metwally, N.A. Khalaf, E. Abdel-Latif and M.A. Ismail, BMC Chem., 17, 6 (2023); https://doi.org/10.1186/s13065-023-00917-2
Y.N. Mabkhot, N.A. Kaal, S. Alterary, M.S. Mubarak, A. Alsayari and A. Bin Muhsinah, J. Heterocycl. Chem., 56, 2845 (2019); https://doi.org/10.1002/jhet.3688
I. Montenegro, E. Sánchez, E. Werner, P. Godoy, Y. Olguín, N. Caro, N. Ehrenfeld and A. Madrid, BMC Chem., 13, 1 (2019); https://doi.org/10.1186/s13065-019-0516-8
A. Alsayari, A. Bin Muhsinah, Y.I. Asiri, K. Venkatesan and Y.N. Mabkhot, Polycycl. Aromat. Compd., 42, 6720 (2022); https://doi.org/10.1080/10406638.2021.1988998
A.U. Isakhanyan, N.Z. Akopyan, G.M. Stepanyan, A.G. Arakelyan, Z.M. Buniatyan, R.E. Muradyan, G.A. Panosyan and A.A. Harutyunyan, Russ. J. Gen. Chem., 92, 2465 (2022); https://doi.org/10.1134/S1070363222110317
Y.N. Mabkhot, N.A. Kaal, S. Alterary, S.S. Al-Showiman, T.A. Farghaly and M.S. Mubarak, Chem. Cent. J., 11, 75 (2017); https://doi.org/10.1186/s13065-017-0307-z
K.C. prasad, B.N. Angothu, T.M. Latha and M. Nagulu, Int. J. Pharm. Biol. Sci., 7, 1 (2017); https://doi.org/10.21276/ijpbs.2017.7.1.1
E. Abdel-Latif, E.M. Keshk, A.G.M. Khalil, A. Saeed and H.M. Metwally, J. Iran. Chem. Soc., 16, 629 (2019); https://doi.org/10.1007/s13738-018-1540-7
S. Bondock, W. Fadaly and M.A. Metwally, Eur. J. Med. Chem., 45, 3692 (2010); https://doi.org/10.1016/j.ejmech.2010.05.018
N.G. Heatley, Biochem. J., 38, 61 (1944); https://doi.org/10.1042/bj0380061