Skip to main navigation menu Skip to main content Skip to site footer
##common.pageHeaderLogo.altText##

Articles

Vol. 2 No. 1 (2011): January – March 2011

Synthesis, Characterization and Biological Activity of novel 3-benzyl-2- (4'-substituted phenyl)-4(5H)-(4''-nitrophenyl amino)-1, 3-oxazolidines

DOI
https://doi.org/10.37285/ijddd.2.1.3
Submitted
November 28, 2024
Published
2024-12-08

Abstract

Here, we describe the design, synthesis, and biological evaluation of oxazolidine derivatives. Oxazolidine ring is a reduced form of oxazole system; many of its derivatives possess interesting biological activities, such as anti-convulsant, anti-microbial, analgesic, anti-inflammatory and anti-tumor. In our study, the biological activity of synthesized novel 3-benzyl-2-(4'-substituted phenyl)-4(5H)-(4''-nitrophenyl amino)-1, 3-oxazolidines 6a-e were characterized by antimicrobial screening against several gram-positive, gram negative bacteria and fungus. The purity of the synthesized compounds was characterized by means of IR, 1H-NMR, mass spectral and elemental analysis. Antimicrobial screening for all the compounds exhibits characteristic microbial inhibition against Bacillus lentus, Micrococcus luteus, Bacillus cereus, Staphylococcus albus, Escherichia coli, Klebsiella aerogenes, Salmonella paratyphi, Proteus vulgaris and Candida albicans

References

  1. [1] Tenover, F.C.; McDonald, L.C. Curr. Opin. Infect. Dis. 2005, 18, 300.
  2. [2] Pfeltz, R.F.; Wilkinson, B.J. Curr. Drug Targets Infect. Disord. 2004, 4, 273.
  3. [3] Roberts, M.C. Curr. Drug Targets Infect. Disord. 2004, 4, 207.
  4. [4] Dessen, A.; Di Guilmi, A.M.; Ernet, T.V.; Dideberg, O. Curr. Drug Targets Infect.Disord. 2001, 1, 63.
  5. [5] Muroi, H.; Nihei, K.; Tsujimoto, K.; Kubo, I. Bioorg. Med. Chem. 2004, 12, 583.
  6. [6] (a) Kan, J. P.; Malnoe, A.; Strolin Benedetti, M. J. Pharm. Pharmacol. 1978, 30, 190. (b) Moureau, F.; Wouters, J.; Vercauteren, D. P.; Collin, S.; Evrard, G.; Durant, F.; Ducrey, F.; Koenig, J. J.; Jarreau, F. X. Eur. J. Med. Chem. 1992, 27, 939. (c) Curet, O.; Damoiseau, G.; Aubin, N.; Sontag, N.; Rovei, V.; Jarreau, F. X. J.Pharm. Exp. Ther. 1996, 277, 253. (d) Ramsay, R. R.; Gravestock, M. B. Mini-Rev.Med. Chem. 2003, 3, 129.
  7. [7] Gante, J.; Juraszyk, H.; Raddatz, P.; Wurziger, H.; Bernotat-Danielowski, S.; Melzer, G.; Rippmann, F. Lett. Pep. Sci. 1995, 2, 135.
  8. [8] (a) Aschwanden, W.; Kyburz, E.; Schoenholzer, P. Helv. Chim. Acta. 1976, 59, 1245. (b) Pruecher, H.; Gottschlich, R.; Haase, A.; Stohrer, M.; Seyfried, C. Bioorg. Med. Chem. Lett. 1992, 2, 165.
  9. [9] (a) Slee, A.M.; Wuonola, M.A.; McRipley, R.J.; Zajac, I.; Zawada, M.J.; Bartholomew, P.T.; Gregory, W.A.; Forbes, M. Antimicrob. Agents Chemother. 1987, 31, 1791. (b) Gregory, W.A.; Brittelli, D.R.; Wang, C.L.; Wuonola, M.A.; McRipley, R.J.; Eustice, D.C.; Eberly,V. S.; Bartholomew, P.T.; Slee, A.M.; Forbes, M. J. Med. Chem. 1989, 32, 1673. (c) Barbachyn, M.R.; Ford, C.W. Angew. Chem. Int. Ed. 2003, 42, 2010; (d) Zappia, G.; Menendez, P.; Delle Monache, G.; Misiti, D.; Nevola, L.; Botta, B. Mini-Rev. Med. Chem. 2007, 7, 389.
  10. [10] (a) Dyen, M.E.; Swern, D. Chem. Rev. 1967, 67, 197; (b) Ager, D.J.; Prakash, I.;
  11. Schaad, D.R. Aldrichim. Acta. 1997, 30, 3. (c) Zappia, G.; Gacs-Baitz, E.; Delle Monache, G.; Misiti, D.; Nevola, L.; Botta, B. Curr. Org. Syn. 2007, 4, 81.
  12. [11] (a) Clemett, D.; Markham, A. Drugs 2000, 59, 815. (b) Perry, C.M.; Javis, B. Drugs 2001, 61, 525. (c) Norrby,R. Exp. Opin. Pharmacother. 2001, 2, 293. (d) Stevens,D.L.; Herr, D.; Lampiris, H.; Hunt, J.L.; Batts, D.H.; Hafkin, B. Clin. Infect. Dis. 2002, 34, 1481.
  13. [12] (a) Ashtekar, D.R.; Costa-Periera, R.; Shrinivasan, T.; Iyyer, R.; Vishvanathan, N.; Rittel, W.S. Diagn. Microbiol. Infect. Dis. 1991, 14, 465. (b) Cynamon,M. H.; Klemens, S.P.; Sharpe, C.A.; Chase, S. Antimicrob. Agents Chemother. 1999, 43, 189. (c) Wallace, R.J., Jr.; Brown-Elliott, B.A.; Ward, S. C.; Crist,C.J.; Mann, L.B.; Wilson, R.W. Antimicrob. Agents Chemother. 2001, 45, 764.
  14. [13] Sood, R.; Bhadauriya, T.; Rao, M.; Gautam, R.; Barman, S.; Malhotra, T.K.; Upadhyay, D.J.; Rattan, A. Infect. Dis. Drug Targets. 2006, 6, 343.
  15. [14] (a) Phillips, O.A.; Udo, E.E.; Ali, A.A. M.; Al-Hassawi,N. Bioorg. Med. Chem. 2003, 11, 35. (b) Reck, F.; Zhou, F.; Girardot, M.; Kern, G.; Eyermann, C.J.; Hales, N.J.; Ramsay, R.R.; Gravestock, M.B. J. Med. Chem. 2005, 48,499. (c) Hauck, S. I.; Cederberg, C.; Doucette, A.; Grosser, L.; Hales, N.J.; Poon, G.; Gravestock, M. B. Bioorg. Med. Chem. Lett. 2007, 17, 337. (d) Phillips, O.A.; Udo, E. E.; Ali, A.A. M.; Samuel, S. M. Eur. J. Med. Chem. 2007, 42, 214.
  16. [15] Zarghi, A.; Najafnia, L.; Daraie, B.; Dadrass, O.G.; Hedayati, M. Bioorg Med Chem Lett. 2007, 17, 5634–5637.
  17. [16] Rameshkumar, N.; Ashokkumar, M.; Subramaniyan,
  18. E. H.; Ilavarasan, R.; Sridhar, S.K. Eur. J. Med. Chem. 2003, 38, 1001–1004.