Synthesis and Biological evaluation of Oxazolone derivatives
Abstract
Some new [4-[3-chloro-benzylidine]-2-phenyl oxazol-5-one and 4-[2-nitro-benzylidine]-2-phenyl oxazol-4-5-one were synthesized in microwave and there structures were confirmed by I.R. and 1H NMR and their antimicrobial screening against E. Coli, Staphylococcus aureus and Candida albicans were established by zone of inhibition.
Keywords:
oxazolonederrivatives, synthesis, characterization, pharmacological activity
References
1. Sanja DB, Sanghani AM, Rajani VR, Godhani DR. Synthesised 4- Oxothiazolidine Derivatives as potential antibacterial and antifungal agents. Int. J. Chem. Sci. 2007, 5(2) : 867-873.
2. Morrison RT, Boyd RN, Boyd RK. Organic Chemistry, 6th edition (1992).
3. Roberts JD, Caserio MC. Basic Principles of Organic Chemistry (1964).
4. Gelmi ML, Clerici F, Melis A. 5(4H)-Oxazolone, part X. acid and base effects on the translactonization reaction of 4-(2-oxa-alkylidene)-5(4H)- oxazolones: new synthesis of 5- alkylidene-3-benzoylamino-2(5H)- furanones. Tetrahedron 1997; 53 : 1843-1854.
5. Croce PD, Ferraccioli R, Rosa CL. J. Chem. Soc. Perkin Trans. 1994; 1: 2499–2502.
6. Cannella R, Clerici F, Gelmi ML, Penso M, Pocar D. J. Org. Chem. 1996; 61: 1854–1856.
7. Bossio R, Marcaccini S, Pepino R, Paoli P. J. Heterocycl. Chem. 1994; 31: 729–732.
8. Arenal I, Bernabe M, Alvarez EF, Izquierdo ML, Penades S. J. Heterocycl. Chem. 1983; 20 : 607–613.
9. Kojima S, Ohkawa H, Hirano T, Maki S, Niwa H, Ohashi M, Inouye S, Tsuji FI. Tetrahedron Lett. 1998; 39 : 5239–5242.
10. Cativiela C, Fraile JM, Garcia JI, Lopez MP, Mayoral JA, Pires E. Diels-Alder reaction of (E)-2-phenyl-4-[(s)-2,2-dimethyl-1,3-dioxolan 4- ylmethylen]-5(4H)-oxazolone with heterogeneous catalysts. Tetrahedron Asymmetry 1996; 7 : 2391-2394.
11. Sun YF, Cui YP. The synthesis, structure and spectroscopic properties of novel oxazolone, pyrazolone and pyrazoline-containing heterocycle chromophores. Dyes and Pigments 2009; 81: 27–34.
12. Ozturk G, Alp S, Timur S. A fluorescent biosensor based on acetylcholinesterase and 5-oxazolone derivative immobilized in polyvinylchloride (PVC) matrix, Journal of Molecular Catalysis B: Enzymatic. 2007; 47 :111–116.
13. Aaglawe MJ, Dhule SS, Bahekar SS, Wakte PS, Shinde DB. Synthesis and Antibacterial Activity of Some Oxazolone Derivatives. Journal of the Korean Chemical Society. 2003; 47 : 133-136.
14. Mesaik MA, Rahat S, Khan KM, Ullah Z, Choudhary MI, Murad S, Ismail Z, Rahman AU, Ahmad A. Synthesis and immunomodulatory properties of selected oxazolone derivatives. Bioorganic and Medicinal Chemistry 2004; 12 : 2049-2057.
15. Khan KA, Mughal UR, Khan MTH, Ullah Z, Perveen S, Choudhary MI. Oxazolones: New tyrosinase inhibitors; synthesis and their structure– activity relationships. Bioorganic and Medicinal Chemistry 2006; 14: 6027-6033.
16. Tikdari AM, Fozooni S, Hamidian H. Dodecatungstophosphoric Acid (H3PW12O40), Samarium and Ruthenium (ІІІ) Chloride Catalyzed Synthesis of Unsaturated 2-Phenyl-5(4H)-oxazolone Derivatives under Solvent-free Conditions. Molecules. 2008; 13: 3246-3252.
17. Dundar Y, Unlu S, Banoglu E, Entrena A, Costantino G, Nunez MT, Ledo F, Sahin FF, Noyanalpan N. Synthesis and biological evaluation of 4, 5-diphenyloxazolone de rivatives on route towards selective COX-2 inhibitors. European Journal of Medicinal Chemistry 2008; 4: 1-8.
2. Morrison RT, Boyd RN, Boyd RK. Organic Chemistry, 6th edition (1992).
3. Roberts JD, Caserio MC. Basic Principles of Organic Chemistry (1964).
4. Gelmi ML, Clerici F, Melis A. 5(4H)-Oxazolone, part X. acid and base effects on the translactonization reaction of 4-(2-oxa-alkylidene)-5(4H)- oxazolones: new synthesis of 5- alkylidene-3-benzoylamino-2(5H)- furanones. Tetrahedron 1997; 53 : 1843-1854.
5. Croce PD, Ferraccioli R, Rosa CL. J. Chem. Soc. Perkin Trans. 1994; 1: 2499–2502.
6. Cannella R, Clerici F, Gelmi ML, Penso M, Pocar D. J. Org. Chem. 1996; 61: 1854–1856.
7. Bossio R, Marcaccini S, Pepino R, Paoli P. J. Heterocycl. Chem. 1994; 31: 729–732.
8. Arenal I, Bernabe M, Alvarez EF, Izquierdo ML, Penades S. J. Heterocycl. Chem. 1983; 20 : 607–613.
9. Kojima S, Ohkawa H, Hirano T, Maki S, Niwa H, Ohashi M, Inouye S, Tsuji FI. Tetrahedron Lett. 1998; 39 : 5239–5242.
10. Cativiela C, Fraile JM, Garcia JI, Lopez MP, Mayoral JA, Pires E. Diels-Alder reaction of (E)-2-phenyl-4-[(s)-2,2-dimethyl-1,3-dioxolan 4- ylmethylen]-5(4H)-oxazolone with heterogeneous catalysts. Tetrahedron Asymmetry 1996; 7 : 2391-2394.
11. Sun YF, Cui YP. The synthesis, structure and spectroscopic properties of novel oxazolone, pyrazolone and pyrazoline-containing heterocycle chromophores. Dyes and Pigments 2009; 81: 27–34.
12. Ozturk G, Alp S, Timur S. A fluorescent biosensor based on acetylcholinesterase and 5-oxazolone derivative immobilized in polyvinylchloride (PVC) matrix, Journal of Molecular Catalysis B: Enzymatic. 2007; 47 :111–116.
13. Aaglawe MJ, Dhule SS, Bahekar SS, Wakte PS, Shinde DB. Synthesis and Antibacterial Activity of Some Oxazolone Derivatives. Journal of the Korean Chemical Society. 2003; 47 : 133-136.
14. Mesaik MA, Rahat S, Khan KM, Ullah Z, Choudhary MI, Murad S, Ismail Z, Rahman AU, Ahmad A. Synthesis and immunomodulatory properties of selected oxazolone derivatives. Bioorganic and Medicinal Chemistry 2004; 12 : 2049-2057.
15. Khan KA, Mughal UR, Khan MTH, Ullah Z, Perveen S, Choudhary MI. Oxazolones: New tyrosinase inhibitors; synthesis and their structure– activity relationships. Bioorganic and Medicinal Chemistry 2006; 14: 6027-6033.
16. Tikdari AM, Fozooni S, Hamidian H. Dodecatungstophosphoric Acid (H3PW12O40), Samarium and Ruthenium (ІІІ) Chloride Catalyzed Synthesis of Unsaturated 2-Phenyl-5(4H)-oxazolone Derivatives under Solvent-free Conditions. Molecules. 2008; 13: 3246-3252.
17. Dundar Y, Unlu S, Banoglu E, Entrena A, Costantino G, Nunez MT, Ledo F, Sahin FF, Noyanalpan N. Synthesis and biological evaluation of 4, 5-diphenyloxazolone de rivatives on route towards selective COX-2 inhibitors. European Journal of Medicinal Chemistry 2008; 4: 1-8.
Statistics
385 Views | 657 Downloads
How to Cite
Dixit, A., G. Garg, N. P. Sharma, D. K. Shrivastava, and A. Sharma. “Synthesis and Biological Evaluation of Oxazolone Derivatives”. Current Research in Pharmaceutical Sciences, Vol. 1, no. 2, Dec. 2011, pp. 86-91, https://crpsonline.com/index.php/crps/article/view/42.
Issue
Section
Research Articles