Synthesis, antibacterial activity of 2,4-disubstituted oxazoles and thiazoles as bioisosteres

Letters in Drug Design and Discovery

Volumn 6, Issue 1, 2009, Pages 21-28

  Kaspady, Mohamed ^a   Narayanaswamy, Venugopala Katharigatta ^b   Raju, Mohana ^a   Rao, Gopal Krishna ^b  

^a SRI KRISHNADEVARAYA UNIVERSITY   (India)

^b AL AMEEN COLLEGE OF PHARMACY   (India)

Author keywords

Antibacterial activity; Bioisostere; Minimum inhibitory concentration; Oxazole; Thiazole

Indexed keywords

ALCOHOL; AMIDE; OXAZOLE DERIVATIVE; OXYGEN; SULFUR; THIAZOLE DERIVATIVE; THIOAMIDE;

ANTIBACTERIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SYNTHESIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 61849106099     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018009787158481     Document Type: Article

References (24)

1. Karl, D.H.; Friedrich, K.H.; James, T.O. N-(4-substituted-thiazolyl) oxamic acid derivatives, new series of potent, orally active antiallergy agents. J. Med. Chem., 1983, 26, 1158-63.
2. William, C.P.; Harriet W.H.; Michael, D.T.; Michael, J.R.; David, G.T.Jr.; Cleo, J.C.C.; Annette, M.D.; Sylvester, R.K.; Ila S.; Steinbaugh, B.A.; Batly, B.L.; Painchaud, C.A.; Rapundalo, S.T.; Michniewicz, B.M.; Olson, S.C.J. Structure-activity relationships of a series of 2-amino-4-thiazole-containing renin inhibitors. J. Med. Chem., 1992, 35, 2562-72.
3. Fortuna, H.; James, D.R.; Robert, W.D.; Francis, A.K.; Roland, L.W,; Steven P.S.; James, H.H.; Patrick, R.Y.; George W.C. 3-[1-(2-Benzoxazolyl) hydrazino] propanenitrile derivatives: inhibitors of immune complex induced inflammation. J. Med. Chem., 1988, 31, 1719-28.
4. Tsuji, K.; Ishikawa, H. Synthesis and anti-pseudomonal activity of new 2-isocephems with a dihydroxypyridone moiety at C-7. Bioorg. Med. Chem. Lett., 1994, 4, 1601-06.
5. Frank, W.B.; Amanda, S.C.; Marita, H.S.; Richard, J.; Nils, G.J.; Christopher, L.J.; Michael, D.K.; Peter, L.; John, M.M.; Noreen, R.; Oberg, B.; Palkowitz, J.A.; Parrish, C.A.; Pranc, J.; Zhang, H.; Zhou, X.X. Phenethylthiazolethiourea (PETT) compounds, a new class of HIV-1 reverse transcriptase inhibitors. 1. Synthesis and basic structure-activity relationship studies of PETT analogs. J. Med. Chem., 1995, 38, 4929-36.
6. Venugopala, K.N.; Jayashree, B.S. Synthesis and characterization of carboxamides of 2′-amino-4′- (6-bromo-3-coumarinyl) thiazole for their analgesic and anti-inflammatory activity. Ind. J. Heterocyclic Chem., 2003, 12, 307-10.
7. Beck, G.; Heitzer, H. U.S. Patent 1998, 4, 748, 243, May 31.
8. Osaka, H. Ul.; Matsubara, N.H.; Kawabe, I.M. U.S. Patent 1993, 5, 180, 833, Jan 19.
9. Gregory, F.H.; Michelle, A.H.; Ramiah, M.; Eric, F.V.S.; James, R.S.; Jason, Yang. 1,3-Dichloropropenes-in the preparation of thiazole derivatives-2-chloro-5-chloromethylthiazole and 5-hydroxymethylthiazole. ARKIVOC, 2001, 6, 94-99.
10. Murugan, R.; Scriven, E.F.V. PCT Int. Appl., 1998, WO 98 45, 279, Oct 15; Chem. Abstr., 1998, 129, 302633v.
11. Jackson, A.; Heyes, G.; Grayson, J.I.; Clarke, R. U.S. Patent 1998, 5, 705, 652, Jan 6.
12. Leanna, R.M.; Morton, H.E. PCT Int. Appl., 1996, WO 96 16, 050, May 30; Chem. Abstr., 1996, 125, 114603d.
13. George, C.; Martin, N.; Ray, R.; Thiourea derivatives of 2-aminooxazoles showing antibacterial and antifungal activity. J. Med. Chem., 1973, 16, 1402-05.
14. Anna, C.G.; Helena, I.M.B.; Scott, G.F.; Clifton, E.B.; Brent, R.C. Antimycobacterial natural products: synthesis and preliminary biological evaluation of the oxazole-containing alkaloid texaline. Tetrahedron Lett., 2005, 46, 7355-57.
15. George, C.; Michael, J.F. Derivatives of 2-aminooxazoles showing antiinflammatory activity. J. Med. Chem., 1971, 14, 1075-77.
16. Venugopala, K.N.; Rao, G.K.; Sanjay, P.P.N. Synthesis and pharmacological study of some novel schiff bases of 4-hydroxy 6-carboxhydrazino benzothiophene analogs. J. Pharma. Toxicol., 2007, 2, 248-55.
17. Venugopala, K.N.; Jayashree, B.S. Synthesis and characterization of schiff bases of aminothiazolyl bromocoumarin for their analgesic and anti-inflammatory activity. Asian J. Chem., 2004, 16, 407-11.
18. Parthapratim, M.; Venugopala, K.N.; Jayashree, B.S.; Row, T.N.G. Concomitant polymorphism in 3-acetylcoumarin: Role of weak CH.. O and C-H...pi interactions. Cryst. Growth Des., 2004, 4, 1105-07.
19. Jacques, Y.G.; Hél ne, L. A remarkably simple conversion of nitriles to thioamides. Phosp. Sul. Sili. Rel. Elem., 1994, 95, 325-26.
20. Rao, G.C. Facile hydration of nitriles to amides using potassium fluoride on alumina. Synth. Commun., 1982, 12, 177-81.
21. Rao, G.K.; Venugopala, K.N.; Sanjay, P.P.N. Novel schiff bases of 4-hydroxy 6-carboxhydrazino benzofuran analogs: synthesis and pharmacological study J. Pharma. Toxicol., 2007, 2, 481-88.
22. Padmavathi, V.; Thriveni, P.; Reddy, G.S.; Deepti, D. Synthesis and antimicrobial activity of novel sulfone-linked bis heterocycles. Eur. J. Med. Chem., 2008, 43, 917-24.
23. Oludotun, A.P.; Edet, E.U.; Santhosh M.S. Synthesis and structureeantibacterial activity of triazolyl oxazolidinones containing long chain acyl moiety. Eur. J. Med. Chem., 2008, 43, 1095-04.
24. Kotretsou, S.; Mingeot-Leclercq, M.P.; Constantinou-Kokotou, V.; Brasseur, R.; Georgiadis, M.P.; Tulkens, P.M. Synthesis and antimicrobial and toxicological studies of amino acid and peptide derivatives of Kanamycin A and Netilmicin. J. Med. Chem., 1995, 38, 4710-19.