Novel Linezolid like Analogues: Synthesis, Characterization and Biological Evaluation Synthesis, characterization and study of some 1, 3-oxazolone-5-one, linezolid
Iranian Journal of Pharmaceutical Sciences,
Vol. 10 No. 2 (2014),
1 April 2014
,
Page 69-78
https://doi.org/10.22037/ijps.v10.40828
Abstract
The synthesis of 4-(substituted benzylidene)-2-(pyrazin-2-yl) oxazol-5(4H)-one was achieved in two steps, In first step, pyrazine-2-carboxamide dissolved in EtOH, 10% KOH solution with ClCH2COOH produced compound 2-(pyrazine-2-carboxamido) acetic acid (II) and in second step, compound (II) in (CH3CO)2O with aromatic aldehyde, and catalyst potassium acetate produced title compounds 4-(substituted benzylidene)-2-(pyrazin-2-yl) oxazol-5(4H)-one (PA1-PA14). All the newly synthesized compounds structure were elucidated using various spectral techniques viz. FT-IR, 1H-NMR, GC-MS spectroscopy, and CHN elemental analysis data and screened for in vitro antimicrobial and antifungal activity. In vitro anti bacterial activity was carried out against organisms E.coli, K.pneumonia, S.aureus, and B. Subtilis as well as antifungal activity were carried out against A.niger and S. cerevisiae activity by minimum inhibitory concentration method. The most promising broad spectrum compounds PA3, PA4, and PA5 were observed and study data reveals that additions of different functional groups had varying effects on activity. In addition, the greater biological activities were observed when the electron-withdrawing groups like fluorine, bromine and chlorine were incorporated at p-position of the phenyl ring.
- Antimicrobial
- Linezolid
- MIC
- 1
- 3-oxazolone-5-one
- FT-IR
- 1H-NMR.
How to Cite
References
[2] Wallace R. J. J, Brown-Elliott B.A, Ward S. C, Crist C. J, Mann L. B, Wilson R. W. A. In vitro activities of linezolid against multiple Nocardia Species. Antimicrob Agents Chemother (2001) 45(4): 1295-1297.
[3] Lois M. E, Ashok R, Michael R. J, Appelbaum P. C. Anti anaerobe activity of RBX 7644 (Ranbezolid), a new oxazolidinone, compared with those of eight other agents. Antimicrob Agents Chemother (2003) 47(3): 1143-1147.
[4]Ahmed S. A. A. Pesticidal effects of some imidazolidine and oxazolone derivatives. World J Agri. Sci.(2009) 5(1): 105-113.
[5]Ahmada et al. Synthesis and immunomodulatory properties of selected oxazolone derivatives. Bioorg. Med. Chem.(2004)12(9):2049-2057.
[6] Khalid M.K, Uzma R. M, Mahmud T. Hassan K, Zia U, Shahnaz P, Muhammad I. C. Oxazolones: New tyrosinase inhibitors; synthesis and their structure-activity relationships. Bioorg. Med. Chem. (2006) 14(17):6027-6033.
[7] Hemashrilatha S, Shruthi K, Manjula A, Harinandha babu V, Vithalrao B. Synthesis and anti-inflammatory activity of imidazo [1,2-a] pyridinyl / pyrazinyl benzamides / acetamides. Indian J. chem. (2012) 51B: 981-987.
[8] Gadada N, Amorn P. Synthesis and antimicrobial activity of oxazolone, imidazolone and triazine derivatives containing benzothiophene. Bull. Korean Chem. Soc. (2011) 32(11): 3914-3922.
[9] Osman M. O. H, Hussein M. H, Evelin B. M, Ahmed El-M. Synthetic approaches and biological evaluation of some new sulfonate ester-containing imidazolone derivatives. Ameri. J. Org. Chem. (2012) 2(4): 79-86.
[10] Sarragiotto et al. Synthesis and evaluation of new β-carboline-3-(4-benzylidene)-4H- oxazol-5-one derivatives as antitumor agents. Molecules (2012) 17: 6100-6113.
[11] Pasha M. A, Jayashankara V. P, Venugopala K.N, Gopalkrishna R. Zinc oxide (ZnO):An Efficient catalyst for the synthesis of 4-arylmethylidene-2-phenyl-5-(4H)-oxazolone having antimicrobial activity. J. Pharmacology and Toxicology (2007) 2(3): 264-270.
[12] Mariappan G, Saha B. P, Sriparna D, Deepak K , Haldar P. K. Design, synthesis and antidiabetic evaluation of oxazolone derivatives. J. Chem. Sci. (2011)123(3): 335-341.
[13] Nicolaou K. C, Pfefferkorn J. A, Roecker A. J, Cao G. Q, Barluenga S, Mitchell H. J. Natural product-like combinatorial libraries based on privileged structures: General principles and solid-phase synthesis of benzopyrans. J. Amer. Chem. Soc (2000)122(41):9939.
[14] Poonam K, Pawan K, Arpana M, Neeraj K. A, Pawan K. S. Synthesis of some novel 4-arylidene pyrazoles as potential antimicrobial agents. Org.Med.Chem.Lett. (2013)3(9):1-7.
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