Copyright (c) 2024 Najma Bajracharya, Sunita Shrestha, Gan Bajracharya
This work is licensed under a Creative Commons Attribution 4.0 International License.
Magnesium Powder-Catalyzed, Highly Efficient, Solvent-Free Synthesis of Amides through N-Acetylation of Amines and their Antibacterial Activity
Corresponding Author(s) : Gan B. Bajracharya
Asian Journal of Chemistry,
Vol. 36 No. 4 (2024): Vol 36 Issue 4, 2024
Abstract
Magnesium powder was found to be an efficient catalyst for the acetylation of amines (1) with Ac2O affording corresponding amides (2) in excellent yields (> 99%). This green synthetic protocol has utilized 2.5 mol% of magnesium powder and a stoichiometric amount of Ac2O (1.2 equiv.). Amides 2a-k were synthesized within a short reaction time (2-3 min) at an ambient temperature under solvent free condition. The products were screened against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Staphylococcus epidermidis bacterial strains. N-(2-Hydroxyphenyl)acetamide (2f) was found most active against Gram-positive S. aureus and S. epidermidis indicating its efficacy in treating skin diseases.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- T. Nomura, T. Iwaki, Y. Narukawa, K. Uotani, T. Hori and H. Miwa, Bioorg. Med. Chem., 14, 3697 (2017); https://doi.org/10.1016/j.bmc.2006.01.036
- A.S. Sheikh, H. Nadeem, M.T. Khan, A. Saeed and B. Murtaza, ACS Omega, 8, 9785 (2023); https://doi.org/10.1021/acsomega.2c05782
- M.D. Altintop, U. Abu-Mohsen, Y. Okay, R. Demirel and Z.A. Kaplancikli, Turk. J. Pharm. Sci., 12, 29 (2015).
- H. Lu, X. Zhou, L. Wang and L. Jin, Molecules, 25, 1772 (2020); https://doi.org/10.3390/molecules25081772
- M.M. Ghorab, A.S. Alqahtani, A.M. Soliman and A.A. Askar, Int. J. Nanomed., 15, 3161 (2020); https://doi.org/10.2147/IJN.S241433
- W. Ang, Y.N. Lin, T. Yang, J.Z. Yang, W.Y. Pi, Y.H. Yang, Y.F. Luo, Y. Deng and Y.Q. Wei, Molecules, 17, 2248 (2012); https://doi.org/10.3390/molecules17022248
- B. Tanwar, A. Kumar, P. Yogeeswari, D. Sriram and A.K. Chakraborti, Bioorg. Med. Chem. Lett., 26, 5960 (2016); https://doi.org/10.1016/j.bmcl.2016.10.082
- R. Zogota, L. Kinena, C. Withers-Martinez, M.J. Blackman, R. Bobrovs, T. Pantelejevs, I. Kanepe-Lapsa, V. Ozola, K. Jaudzems, E. Suna and A. Jirgensons, Eur. J. Med. Chem., 163, 344 (2019); https://doi.org/10.1016/j.ejmech.2018.11.068
- S.K. Tipparaju, S.P. Muench, E.J. Mui, S.N. Ruzheinikov, J.Z. Lu, S.L. Hutson, M.J. Kirisits, S.T. Prigge, C.W. Roberts, F.L. Henriquez, A.P. Kozikowski, D.W. Rice and R.L. McLeod, J. Med. Chem., 53, 6287 (2010); https://doi.org/10.1021/jm9017724
- A.P.G. Nikalje, S. Choudhari and H. Une, Eur. J. Exp. Biol., 2, 1302 (2012).
- Md..J Naim, Md.J. Alam, F. Nawaz, V.G.M. Naidu, S. Aaghaz, M. Sahu, N. Siddiqui and O. Alam, Bioorg. Chem., 73, 24 (2017); https://doi.org/10.1016/j.bioorg.2017.05.007
- S. Kumar, A.K. Wahi and R. Singh, Trop. J. Pharm. Res., 10, 265 (2011); http://dx.doi.org/10.4314/tjpr.v10i3.6
- S. Ölgen, F. Bakar, S. Aydin, D. Nebioglu and S. Nebioglu, J. Enzyme Inhib. Med. Chem., 28, 58 (2013); https://doi.org/10.3109/14756366.2011.631183
- H. Jawed, S.U.A. Shah, S. Jamall and S.U. Simjee, Int. Immunopharmacol., 10, 900 (2010); https://doi.org/10.1016/j.intimp.2010.04.028
- P. Rani, D. Pal, R.R. Hegde and S.R. Hashim, J. Chemother., 28, 255 (2016); https://doi.org/10.1179/1973947815Y.0000000060
- A.K. Ghose, V.N. Viswanadhan and J.J. Wendoloski, J. Comb. Chem., 1, 55 (1999); https://doi.org/10.1021/cc9800071
- J.S. Carey, D. Laffan, C. Thomson and M.T. Williams, Org. Biomol. Chem., 4, 2337 (2006); https://doi.org/10.1039/B602413K
- R. Wolf and S. Brenner, Dermatology, 189, 1 (1994); https://doi.org/10.1159/000246749
- P. Rajput and A. Sharma, J. Pharmacol. Med. Chem., 2, 22 (2018).
- A. Kokel, C. Schäfer and B. Török, Curr. Org. Synth., 16, 615 (2019); https://doi.org/10.2174/1570179416666190206141028
- G.B. Bajracharya and S.S. Shrestha, Synth. Commun., 48, 1688 (2018); https://doi.org/10.1080/00397911.2018.1459721
- D.H. Kim, J. Heterocycl. Chem., 13, 179 (1976); https://doi.org/10.1002/jhet.5570130201
- T.S. Ibrahim, I.A. Seliem, S.S. Panda, A.M.M. Al-Mahmoudy, Z.K.M. Abdel-Samii, N.A. Alhakamy, H.Z. Asfour and M. Elagawany, Molecules, 25, 2501 (2020); https://doi.org/10.3390/molecules25112501
- A. Ami´c and M. Molnar, Org. Prep. Proc. Int., 49, 249 (2017); https://doi.org/10.1080/00304948.2017.1320914
- N. Anbu, N. Nagarjun, M. Jacob, J.M.V.K. Kalaiarasi and A. Dhakshinamoorthy, Chemistry, 1, 69 (2019); https://doi.org/10.3390/chemistry1010006
- M.T. Sangole, S.M. Thorat, S.P. Deshmukh, M. Muthukrishnan, S. Shirsath and M. Mujahid, Indian J. Chem., 58B, 1125 (2019).
- S.A. Trujillo, D. Peña-Solórzano, O.R. Bejarano and C. Ochoa-Puentes, RSC Adv., 10, 40552 (2020); https://doi.org/10.1039/D0RA06871C
- Y. Umar, A. Abu-Thabit, P. Jerabek and P. Ramasami, J. Theor. Comput. Chem., 18, 1950009 (2019); https://doi.org/10.1142/S0219633619500093
- J. Yin, J. Zhang, C. Cai, G.J. Deng and H. Gong, Org. Lett., 21, 387 (2019); https://doi.org/10.1021/acs.orglett.8b03542
- G.R. Lloyd, D.Q.M. Craig and A. Smith, J. Pharm. Sci., 86, 991 (1997); https://doi.org/10.1021/js970137w
- J.L. Jat, P. Kumar, S. Verma, D. Chandra, V. Singh and B. Tiwari, New J. Chem., 46, 14782 (2022); https://doi.org/10.1039/D2NJ02755K
- P. Lian, R. Li, X. Wan, Z. Xiang, H. Liu, Z. Cao and X. Wan, Org. Chem. Front., 9, 311 (2022); https://doi.org/10.1039/D1QO01613J
- E. Kianmehr and S.B. Nasab, Eur. J. Org. Chem., 6447 (2018); https://doi.org/10.1002/ejoc.201800779
- A.K. Chakraborti and R. Gulhane, Chem. Commun., 1896 (2003); https://doi.org/10.1039/B304178F
- C. Perez, M. Pauli and P. Bazerque, Acta Biol. Med. Exp., 15, 113 (1990).
- R.K. Gupta, G.M.S. Thakuri, G.B. Bajracharya and R.N. Jha, Bibechana, 18, 143 (2021); https://doi.org/10.3126/bibechana.v18i2.31234
- C.M. Nemkul, G.B. Bajracharya and I. Shrestha, J. Plant Resour., 19, 151 (2021).
- Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard, 9th Edn, CLSI Document M07-A9, vol. 32, No. 2, Clinical and Laboratory Standards Institute, Wayne, PA (2012).
- R. Jagessar and D. Rampersaud, New York Sci. J., 1, 22 (2008).
- M.S. Hifnaway, H.M. Hassan, R. Mohammed, M.M. Fouda, A.M. Sayed, A.A. Hamed, S.F. AbouZid, M.E. Rateb, H.A. Alhadrami and U.R. Abdelmohsen, Mar. Drugs, 18, 243 (2020); https://doi.org/10.3390/md18050243
- Z. Shang, X. Li, L. Meng, C. Li, S. Gao, C. Huang and B. Wang, Chin. J. Ocean Limnol., 30, 305 (2012); https://doi.org/10.1007/s00343-012-1075-1
- Y. Dashti, T. Grkovic, U.R. Abdelmohsen, U. Hentschel and R.J. Quinn, Mar. Drugs, 12, 3046 (2014); https://doi.org/10.3390/md12053046
- J. Wang, W. He, X. Qin, X. Wei, X. Tian, L. Liao, S. Liao, B. Yang, Z. Tu, B. Chen, F. Wang, X. Zhou and Y. Liu, RSC Adv., 5, 68736 (2015); https://doi.org/10.1039/C5RA10828D
- B. Peng, Q. Peng, J. She, B. Yang and X. Zhou, Rec. Nat. Prod., 16, 639 (2022); http://doi.org/10.25135/rnp.312.22.01.2314
- K. Perveen, F. Hanif, H. Jawed and S.U. Simjee, BioMed Res. Int., 635143 (2013); https://doi.org/10.1155/2013/635143
- A. Gul, B. Kunwar, M. Mazhar, K. Perveen, S.U. Simjee, Inflammation, 40, 1177 (2017); https://doi.org/10.1007/s10753-017-0561-1
- A. Arif, S. Majeed, S.U. Simjee, M. Sarfaraz, S.S. Kashif, M. Lodhi, N. Khatian, A. Aziz and H.K. Majeed, Pak-Euro J. Med. Life Sci., 5, 309 (2022); https://doi.org/10.31580/pjmLs.v5i2.2528
- A. Aziz, F. Hanif, S. Majeed, K. Iftikhar and S.U. Simjee, Toxicol. in Vitro, 60, 296 (2019); https://doi.org/10.1016/j.tiv.2019.06.011
- F. Hanif, K. Perveen, H. Jawed, A. Ahmed, S.M. Malhi, S. Jamall and S.U. Simjee, Cancer Cell Int., 14, 133 (2014); https://doi.org/10.1186/s12935-014-0133-5
References
T. Nomura, T. Iwaki, Y. Narukawa, K. Uotani, T. Hori and H. Miwa, Bioorg. Med. Chem., 14, 3697 (2017); https://doi.org/10.1016/j.bmc.2006.01.036
A.S. Sheikh, H. Nadeem, M.T. Khan, A. Saeed and B. Murtaza, ACS Omega, 8, 9785 (2023); https://doi.org/10.1021/acsomega.2c05782
M.D. Altintop, U. Abu-Mohsen, Y. Okay, R. Demirel and Z.A. Kaplancikli, Turk. J. Pharm. Sci., 12, 29 (2015).
H. Lu, X. Zhou, L. Wang and L. Jin, Molecules, 25, 1772 (2020); https://doi.org/10.3390/molecules25081772
M.M. Ghorab, A.S. Alqahtani, A.M. Soliman and A.A. Askar, Int. J. Nanomed., 15, 3161 (2020); https://doi.org/10.2147/IJN.S241433
W. Ang, Y.N. Lin, T. Yang, J.Z. Yang, W.Y. Pi, Y.H. Yang, Y.F. Luo, Y. Deng and Y.Q. Wei, Molecules, 17, 2248 (2012); https://doi.org/10.3390/molecules17022248
B. Tanwar, A. Kumar, P. Yogeeswari, D. Sriram and A.K. Chakraborti, Bioorg. Med. Chem. Lett., 26, 5960 (2016); https://doi.org/10.1016/j.bmcl.2016.10.082
R. Zogota, L. Kinena, C. Withers-Martinez, M.J. Blackman, R. Bobrovs, T. Pantelejevs, I. Kanepe-Lapsa, V. Ozola, K. Jaudzems, E. Suna and A. Jirgensons, Eur. J. Med. Chem., 163, 344 (2019); https://doi.org/10.1016/j.ejmech.2018.11.068
S.K. Tipparaju, S.P. Muench, E.J. Mui, S.N. Ruzheinikov, J.Z. Lu, S.L. Hutson, M.J. Kirisits, S.T. Prigge, C.W. Roberts, F.L. Henriquez, A.P. Kozikowski, D.W. Rice and R.L. McLeod, J. Med. Chem., 53, 6287 (2010); https://doi.org/10.1021/jm9017724
A.P.G. Nikalje, S. Choudhari and H. Une, Eur. J. Exp. Biol., 2, 1302 (2012).
Md..J Naim, Md.J. Alam, F. Nawaz, V.G.M. Naidu, S. Aaghaz, M. Sahu, N. Siddiqui and O. Alam, Bioorg. Chem., 73, 24 (2017); https://doi.org/10.1016/j.bioorg.2017.05.007
S. Kumar, A.K. Wahi and R. Singh, Trop. J. Pharm. Res., 10, 265 (2011); http://dx.doi.org/10.4314/tjpr.v10i3.6
S. Ölgen, F. Bakar, S. Aydin, D. Nebioglu and S. Nebioglu, J. Enzyme Inhib. Med. Chem., 28, 58 (2013); https://doi.org/10.3109/14756366.2011.631183
H. Jawed, S.U.A. Shah, S. Jamall and S.U. Simjee, Int. Immunopharmacol., 10, 900 (2010); https://doi.org/10.1016/j.intimp.2010.04.028
P. Rani, D. Pal, R.R. Hegde and S.R. Hashim, J. Chemother., 28, 255 (2016); https://doi.org/10.1179/1973947815Y.0000000060
A.K. Ghose, V.N. Viswanadhan and J.J. Wendoloski, J. Comb. Chem., 1, 55 (1999); https://doi.org/10.1021/cc9800071
J.S. Carey, D. Laffan, C. Thomson and M.T. Williams, Org. Biomol. Chem., 4, 2337 (2006); https://doi.org/10.1039/B602413K
R. Wolf and S. Brenner, Dermatology, 189, 1 (1994); https://doi.org/10.1159/000246749
P. Rajput and A. Sharma, J. Pharmacol. Med. Chem., 2, 22 (2018).
A. Kokel, C. Schäfer and B. Török, Curr. Org. Synth., 16, 615 (2019); https://doi.org/10.2174/1570179416666190206141028
G.B. Bajracharya and S.S. Shrestha, Synth. Commun., 48, 1688 (2018); https://doi.org/10.1080/00397911.2018.1459721
D.H. Kim, J. Heterocycl. Chem., 13, 179 (1976); https://doi.org/10.1002/jhet.5570130201
T.S. Ibrahim, I.A. Seliem, S.S. Panda, A.M.M. Al-Mahmoudy, Z.K.M. Abdel-Samii, N.A. Alhakamy, H.Z. Asfour and M. Elagawany, Molecules, 25, 2501 (2020); https://doi.org/10.3390/molecules25112501
A. Ami´c and M. Molnar, Org. Prep. Proc. Int., 49, 249 (2017); https://doi.org/10.1080/00304948.2017.1320914
N. Anbu, N. Nagarjun, M. Jacob, J.M.V.K. Kalaiarasi and A. Dhakshinamoorthy, Chemistry, 1, 69 (2019); https://doi.org/10.3390/chemistry1010006
M.T. Sangole, S.M. Thorat, S.P. Deshmukh, M. Muthukrishnan, S. Shirsath and M. Mujahid, Indian J. Chem., 58B, 1125 (2019).
S.A. Trujillo, D. Peña-Solórzano, O.R. Bejarano and C. Ochoa-Puentes, RSC Adv., 10, 40552 (2020); https://doi.org/10.1039/D0RA06871C
Y. Umar, A. Abu-Thabit, P. Jerabek and P. Ramasami, J. Theor. Comput. Chem., 18, 1950009 (2019); https://doi.org/10.1142/S0219633619500093
J. Yin, J. Zhang, C. Cai, G.J. Deng and H. Gong, Org. Lett., 21, 387 (2019); https://doi.org/10.1021/acs.orglett.8b03542
G.R. Lloyd, D.Q.M. Craig and A. Smith, J. Pharm. Sci., 86, 991 (1997); https://doi.org/10.1021/js970137w
J.L. Jat, P. Kumar, S. Verma, D. Chandra, V. Singh and B. Tiwari, New J. Chem., 46, 14782 (2022); https://doi.org/10.1039/D2NJ02755K
P. Lian, R. Li, X. Wan, Z. Xiang, H. Liu, Z. Cao and X. Wan, Org. Chem. Front., 9, 311 (2022); https://doi.org/10.1039/D1QO01613J
E. Kianmehr and S.B. Nasab, Eur. J. Org. Chem., 6447 (2018); https://doi.org/10.1002/ejoc.201800779
A.K. Chakraborti and R. Gulhane, Chem. Commun., 1896 (2003); https://doi.org/10.1039/B304178F
C. Perez, M. Pauli and P. Bazerque, Acta Biol. Med. Exp., 15, 113 (1990).
R.K. Gupta, G.M.S. Thakuri, G.B. Bajracharya and R.N. Jha, Bibechana, 18, 143 (2021); https://doi.org/10.3126/bibechana.v18i2.31234
C.M. Nemkul, G.B. Bajracharya and I. Shrestha, J. Plant Resour., 19, 151 (2021).
Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard, 9th Edn, CLSI Document M07-A9, vol. 32, No. 2, Clinical and Laboratory Standards Institute, Wayne, PA (2012).
R. Jagessar and D. Rampersaud, New York Sci. J., 1, 22 (2008).
M.S. Hifnaway, H.M. Hassan, R. Mohammed, M.M. Fouda, A.M. Sayed, A.A. Hamed, S.F. AbouZid, M.E. Rateb, H.A. Alhadrami and U.R. Abdelmohsen, Mar. Drugs, 18, 243 (2020); https://doi.org/10.3390/md18050243
Z. Shang, X. Li, L. Meng, C. Li, S. Gao, C. Huang and B. Wang, Chin. J. Ocean Limnol., 30, 305 (2012); https://doi.org/10.1007/s00343-012-1075-1
Y. Dashti, T. Grkovic, U.R. Abdelmohsen, U. Hentschel and R.J. Quinn, Mar. Drugs, 12, 3046 (2014); https://doi.org/10.3390/md12053046
J. Wang, W. He, X. Qin, X. Wei, X. Tian, L. Liao, S. Liao, B. Yang, Z. Tu, B. Chen, F. Wang, X. Zhou and Y. Liu, RSC Adv., 5, 68736 (2015); https://doi.org/10.1039/C5RA10828D
B. Peng, Q. Peng, J. She, B. Yang and X. Zhou, Rec. Nat. Prod., 16, 639 (2022); http://doi.org/10.25135/rnp.312.22.01.2314
K. Perveen, F. Hanif, H. Jawed and S.U. Simjee, BioMed Res. Int., 635143 (2013); https://doi.org/10.1155/2013/635143
A. Gul, B. Kunwar, M. Mazhar, K. Perveen, S.U. Simjee, Inflammation, 40, 1177 (2017); https://doi.org/10.1007/s10753-017-0561-1
A. Arif, S. Majeed, S.U. Simjee, M. Sarfaraz, S.S. Kashif, M. Lodhi, N. Khatian, A. Aziz and H.K. Majeed, Pak-Euro J. Med. Life Sci., 5, 309 (2022); https://doi.org/10.31580/pjmLs.v5i2.2528
A. Aziz, F. Hanif, S. Majeed, K. Iftikhar and S.U. Simjee, Toxicol. in Vitro, 60, 296 (2019); https://doi.org/10.1016/j.tiv.2019.06.011
F. Hanif, K. Perveen, H. Jawed, A. Ahmed, S.M. Malhi, S. Jamall and S.U. Simjee, Cancer Cell Int., 14, 133 (2014); https://doi.org/10.1186/s12935-014-0133-5