Synthesis of Novel 3-Acetyl N-methyl-2- Quinolone Derivatives with Expected Antimicrobial Activity

Ghazwan Ali Salman

doi:10.23851/mjs.v28i2.502

Authors

Ghazwan Ali Salman Department of Chemistry, College of Sciences, Mustansiriyah University, IRAQ

DOI:

https://doi.org/10.23851/mjs.v28i2.502

Keywords:

Quinolines, Oxadiazoles, Antimicrobial activity

Abstract

A series of new 3-Acetyl N-Methyl-2-quinolones oxadiazoles derivatives were synthesized by reaction of 3-acetyl-4-hydroxy-1-methylquinolin-2(1H)-one 3 with ethylbromoacetate to produce compounds 4. The hydrazinolysis of compound 4 with hydrazine hydrate afforded hydrazide compounds 5. New Schiff bases 6 were obtained by condensation of compound 5 with different aryl aldehydes. The last step involves refluxing compound 6 with acetic anhydrides to give the corresponding 3-acetyl-N-methylquinolin-2-one oxadiazoles 7. All the synthesized compounds were characterized on the basis of FT-IR, 1H-NMR and 13C-NMR. The synthesized compounds have been evaluated for antimicrobial activity against Gram-positive and Gram-negative bacteria. Among sixteen synthesized novel compounds, in which five compounds (7a, 7b, 7c, 7e, 7g) ex-hibited promising Antimicrobial activity as compared to Trimethoprim (100μg/ml).

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References

[ 1 ] a) Ukita C. ; Mizuno D. Chem. Pharm. Bull 1960, 8, 1016: b) Schering Corp. (by Afon-so A. ; Weinstein J. ; Gentles M. J. ; Rosen-blum S. B.), PCT Int. Appl. WO 92004328, 1992; Chem. Abstr.1992, 117, 90162r; c) Ukita C. ; Mizuno D. ; Tamura T. ; Yama-kawa T. ; Nojima S. ; J. Chem. Pharm. SOC. Jap.1951, 71 234; d) Williams D. R. ; Bremmer M. L. ; Brown D. L. ; Antuono J. D. ; J. Org. Chem.1985, 50, 2807; e) Wat C. K. ; Innes A. G. ; Smith D. G. ; Wright J. L. C. ; Vining L. C. ; Can. J. Chem.1977, 55, 4090; f) Williams D. R. ; Sit S. Y. ; J. Org. Chem.1982, 47, 2846; g) Cutler H. G. ; Ja-cyno J. M. ; Agric. Biol. Chem.1991, 55, 2629; h) Tanabe Y. ; Miyakado M. ; Ohno N. ; Yoshioka H. ; Chem. Lett.1982, 1543; i) Irschik H. ; Jansen R. ; Hople G. ; Gert K. ; Reichenbach H. ; J. Antibiotics 1985, 38, 145; j) Cook L. ; Ternai B. ; Gosh P. ; JMed. Chem.1987, 30, 1017.

[ 2 ] Abass, M. ; Mostafa, B. B. Bioorg. Med. Chem.2005, 13, 6133-6144.

[ 3 ] El-Shennawy,A. M. ; Mohamed A. H. ;Abass M. Medscape J. Med.2007, 9,15-33.

[ 4 ] Detsi, A. ; Bouloumbasi, D. ; Prousis, K. C. ; Koufaki, M. ; Athanasellis, G. ; Melagraki, G. ; Afantitis, A. ; Igglessi-Markopoulou, O. ; Kontogiorgis, C. ; Hadjipavlou-Litina, D. J. Med. Chem.2007, 50, 2450-2458.

[ 5 ] Rivkin, A. ; Kim, Y. R. ; Goulet, M. T. ; Bays, N. ; Hill, A. D. ; Kariv, I. ; Krauss, S. ; Ginanni, N. ; Strack, P. R. ; Kohl, N. E. ; Chung, C. C. ; Varnerin, J. P. ; 5. Goudreau, P. N. ; Chang, A. ; Tota, M. R. ; Munoz, B. Bioorg. Med. Chem. Lett.2006, 16, 4620-4623.

[ 6 ] Tani, M. ; Harimaya, K. ; Gyobu, Y. ; Sasa-ki, T. ; Takennouchi, O. ; Kawamura, T. ; Kamimura, T. ; Harada, T. J. Antibiot.2004, 57,89-96.

[ 7 ] Snider, B. B. ; Wu X. Heterocycles 2006, 70, 279-294.

[ 8 ] Ahvale, A. B. ; Prokopcová, H. ; Šefčovičová, J. ; Steinschifter, W. ; Täubl, A. E. ; Uray, G. ; Stadlbauer, W. Eur. J. Org. Chem.2008, 563-571.

[ 9 ] "Ukrainets, I. V. ; Tkach, A. A. ; Yang, L. Y. Chem. Heterocycl. compds.2008, 44, 1347-1354.

[ 10 ] Mohamed, E. A. ; Ismail, M. M. ; Gabr, Y. ; Abass, M. ; Farrag, H. A. Indian J. Chem.1995,34B, 21-26.

[ 11 ] "Mohamed, E. A. ; Ismail, M. M. ; Gabr, Y. ; Abass, M. J. Serb. Chem. Soc.1993, 58, 737-743.

[ 12 ] "Stadlbauer, W. ; Badawey, E. ; Hojas, G. ; Roschger, P. ; Kappe, T. Molecules 2001, 6, 338-352.

[ 13 ] "Watters, W. H. ; Ramachandran, V. N. J. Chem. Research (S) 1997, 184-185; J. Chem. Research (M) 1997, 1201-1215.

[ 14 ] "O’Donnell, F. ; Smyth, T. J. P. ; Ramachandran, V. N. ; Smyth, W. F. Inter. J. Antimicrob. Agents 2010, 35, 30-38.

[ 15 ] Hall, A. ; Brown, S. H. ; Chowdhury,

A. ; Giblin, G. M. P. ; Gibson, M. ; Healy, M. P. ; Livermore, D. G. ; Wilson, R. J. M. ; Naylor, A. ; Rawlings, D. A. Bioorg. Med. Chem. Lett.2007,17,4450–4455.

[ 16 ] "Abdel-Hamid, M. K. ; Abdel-Hafez, A. A. ; El-Koussi, N. A. ; Mahfouz, N. M. ; Innocenti, A. ; Supuran, C. T. Bioorg. Med. Chem.2007, 15,6975-6984.

[ 17 ]" Amir, M. ; Kumar, H. ; Javed, S. A. Med. Chem. Lett.2007, 17, 4504–4508.

[ 18 ] "Pastorin, G. ; da Ros, T. ; Bolcato, C. ; Montopoli, C. ; Moro, S. ; Cacciari, B. ; Baraldi, P. G. ; Varani, K. ; Borea, P. A. ; Spalluto, G. J. Med. Chem.2006, 49, 1720-1729.

[ 19 ] Wolfgang, S. ; Gerhard, H. Heterocyclic Chem.2004, 41, 681.

[ 20 ] Abdullah, S. ; Naceur, H. Molecules 2014, 19,911-924.

[ 21 ] Fairbrother RW; Martyn G. J Clin Pathol 1951, 4, 374–77.

[ 22 ] Gould JC; Bowie JH. Edinb med J 1952, 59, 178–99.

[ 23 ] Handan A; Oznur A; Seher B; Gulten O; Melten U; Dilek S. Turk J Chem 2005, 29, 425–35.

[ 24 ] Wolfson J; Hooper DC. Clini Microbiol Rev.1989, 2(4), 378–24.