Design and synthesis of some novel sulfamethoxazole derivatives bearing -lactam moiety and evaluate their antibacterial activities
Keywords:
sulfamethoxazole, cycloaddition, β-lactam, antibacterialAbstract
A series of novel sulfamethoxazole derivatives were synthesized using the appropriate route. The 4-((4-amino-2,5- dimethyiphenyl) diazenyl)-N-(5-meth-ylisoxazol-3-yl) benzene sulfonamide was synthesized using SMX 1 as diazonium component via diazotization reaction by NaNO2/HCl. The diazonium salt thus obtained was coupled, using the standard experimental procedure, to a range of 2,5-dimethylaniline to afford the requisite azo dye in good yield. The Schiff base derivatives were obtained by the condensation reaction of a compound 2 with various aldehydes to give compounds 3a-f, which undergo [2+2] cycloaddition reaction with chloroacetyl chloride to produce substituted β-lactam derivatives 4a-f. Results obtained from spectroscopic (FT-IR, 1H NMR, and 13C NMR) of synthesized compounds were in very good agreement with their chemical structure. The antibacterial activity of some of these compounds was studied in vitro by disk diffusion against two G+ (Staphylococcus aureus, Streptococcus pneumonia) and two G- (Escherichia coli, Klebsiella pneumonia).
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P. Hammann, L. Halby, P. B. Arimondo, P. Glaser, B. Aigle, H. B.
Bode, O.Genilloud, A. W. Truman, K. J. Weissman, M. Graz, S.
Donadio, L Fraisse, L J. V Piddock, I. H. Gilbert, H. E. Moser,
Nat Rev. Chem.2021, 5,726-749.
F. C. Tenover, Am. J. Med. 2006, 779, DOI
1016/j.amjmed.2006.03.011.
D. Rodr, M. Pernas, A. Rodr, E. Colcho, J. Med. Chem. 2020,
, 1859-1881.
R. Kaur, R. Singh, A. Kumar, S. Kaur, N. Priyadarshi, N. K.
Singhal, K. Singh, Heliyon 2020, 6, e04241.
D. Abdelhamid, n.d., DOI 10.1016/j.bmcl.2009.01.104.
P. K. Prabhakar, n.d., DOI 10.1007/s00044-010-9342-1.
S. M. Hell, C. F. Meyer, G. Laudadio, A. Misale, M. C. Willis, T. Noel,
A. A. Trabanco, V. Gouverneur, J. Am. Chem. Soc. 2020, 742,
-725.
J. Davies, Microbiologia1996, 72, 9-16.
S. B. Christensen, Molecules 2021, 26,1-32.
G. Prasannamedha, P. S. Kumar, J. Clean. Prod. 2020, 250,
S. Kumar Verma, R. Verma, F. Xue, P. Kumar Thakur, Y. R.
Girish, K. P. Rakesh, Bioorg. Chem. 2020, 105,104400.
D. C. Wallace Jr, Richard J and Septimus, Edward J and
Williams Jr, Temple W and Conklin, Richard H and
Satterwhite, Terry K and Bushby, Margaret B and
Hollowell, Rev. Infect. Dis.1982, 4, 196-236.
F. Eugene-Osoikhia, T.T., Aleem, A. O and Ayeni, FUDMA J.
Sci. 2020, 4, 217-232.
P. Eliopoulos, G. M., & Huovinen, Clin. Infect. Dis. 2001, 32,
-1614.
S. Hosseyni, A. Jarrahpour, Org. Biomol. Chem. 2018, 76,
-6852.
M. W. Grinstaff, A. S. Balijepalli, J. H. McNeely, A. Hamoud,
J. Org. Chem. 2020, 85,12044-12057.
R. B. Hamed, J. R. Gomez-Castellanos, L. Henry, C. Ducho,
M. A. McDonough, C. J. Schofield, Nat. Prod. Rep. 2013,
, 21-107.
R. Heiran, S. Sepehri, A. Jarrahpour, C. Digiorgio, H. Douafer,
J. M. Brunel, A. Gholami, E. Riazimontazer, E. Turos,
Bioorg. Chem. 2020, 702, DOI
1016/j.bioorg.2020.104091.
V. Mehra, P. Singh, N. Manhas, V. Kumar, Synlett 2014, 25,
-1126.
A. Mermer, H. Bayrak, S. Alyar, M. Alagumuthu, J. Mol.
Struct. 2020, 1208, 127891.
S. Y.and F. K. NESRIN SENER, IZZET SENER, Asian J. Chem.
, 27, 3658-3662.
F. Cuenu, N. Munoz-Patino, J. E. Torres, R. Abonia, R. A.
Toscano, J. Cobo, J. Mol. Struct. 2017, 1148, 557-567.
I. H. R. Tomi, A. H. R. Al-Daraji, R. R. T. Al-Qaysi, M. M. Hasson,
K. H. D. Al-Dulaimy, Arab. J. Chem. 2014, 7, 687-694.
S. Ozkinah, M. Gur, N. §ener, S. Alkin, M. S. Qavu$, J. Mol.
Struct. 2018, 7774, 74-83.
O. Bekircan, H. Bektas, Molecules 2008, 13, 2126-2135.
A. N. Kursunlu, E. Guler, H. Dumrul, O. Kocyigit, I. H. Gubbuk,
Appl. Surf. Sci. 2009, 255, 8798-8803.
M. Ozil, H. T. Balaydm, M. §enturk, Bioorg. Chem. 2019, 86,
-713.
S. Imran, M. Taha, N. H. Ismail, K. M. Khan, F. Naz, M.
Hussain, S. Tauseef, Molecules 2014, 79, 11722-11740.
H. Aziz, A. Mahmood, S. Zaib, A. Saeed, H. R. El-Seedi, J.
Pelletier, J. Sevigny, J. Iqbal, J. Biomol. Struct. Dyn. 2021,
, 6140-6153.
H. Lal, N. Sharma, T. P. Agarwal, N. Sharma, J. Appl. Pharm.
Sci. 2012, 2, 104-112.
N. Borazjani, M. Behzadi, M. Dadkhah Aseman, A. Jarrahpour, J.
A. Rad, S. Kianpour, A. Iraji, S. M. Nabavizadeh, M. M.
Ghanbari,G.Batta, E.Turos,Med.Chem. Res.2020,29, ASS¬
ISTS.
A. Bishnoi, K. Srivastava, S. Singh, C. M. Tripathi, Eur. J.
Chem. 2011, 2, 359-364.
V. Akbary Moghaddam, V. Kasmaeifar, Z. Mahmoodi, H. Ghafouri,
O.Saberi, A.Mohammadi, Int.J. Biol. Macromol.2021,189,194-
N. Berber, M. Arslan, Q. Bilen, Z. Sackes, N. Genper, O. Arslan,
Bioorg. Khim. 2015, 47, 468-474
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