Synthesis and Microbiological Activities of Novel Acyclic Nitrones

Cherifa Mahieddine; Mohamed Salah Boukhechem; Said Zerkout; Abdelghani Zitouni

doi:10.14233/ajchem.2016.19576

Issue

Vol. 28 No. 5 (2016): Vol 28 Issue 5

Issue Published : January 30, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Microbiological Activities of Novel Acyclic Nitrones

https://doi.org/10.14233/ajchem.2016.19576

Cherifa Mahieddine

Laboratoire de Recherche sur les Produits Bioactifs et la Valorisation de la Biomasse, Ecole Normale Supérieure-Vieux Kouba, B.P.: 92, 16038 Kouba, Alger, Algeria

Mohamed Salah Boukhechem

Laboratoire de Recherche sur les Produits Bioactifs et la Valorisation de la Biomasse, Ecole Normale Supérieure-Vieux Kouba, B.P.: 92, 16038 Kouba, Alger, Algeria

Said Zerkout

Laboratoire de Recherche sur les Produits Bioactifs et la Valorisation de la Biomasse, Ecole Normale Supérieure-Vieux Kouba, B.P.: 92, 16038 Kouba, Alger, Algeria

Abdelghani Zitouni

Laboratoire de Recherche sur les Produits Bioactifs et la Valorisation de la Biomasse, Ecole Normale Supérieure-Vieux Kouba, B.P.: 92, 16038 Kouba, Alger, Algeria

Corresponding Author(s) : Cherifa Mahieddine

mahieddinec@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 5 (2016): Vol 28 Issue 5
Article Published : January 30, 2016

Abstract

In this article, the synthesis, antibacterial and antifungal activities of a-(5-(R)-2-thiophyl)-N-(4-R’) phenyl nitrones are reported. The synthesis was achieved by the condensation of N-substituted hydroxylamine [4-R’-phenylhydroxylamine] with 5-R-2-thiophene-carboxaldehyde in boiling absolute ethanol. The chemical structure of this nitrones was identified by spectroscopic techniques (IR and NMR). The antibacterial and antifungal activities were evaluated against bacteria: B. substilis, S. aureus, E. coli, S. enterica and fungus: M. ramannianus and F. oxysporium f.sp. albedinis. The reactivity of this reaction was making clear according the director condition.

Keywords

Antibacterial Antifungal Nitrones Thiophene

Mahieddine, C., Boukhechem, M. S., Zerkout, S., & Zitouni, A. (2016). Synthesis and Microbiological Activities of Novel Acyclic Nitrones. Asian Journal of Chemistry, 28(5), 1027–1030. https://doi.org/10.14233/ajchem.2016.19576

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References

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G. Barriga, C. Olea-Azar, E. Norambuena, A. Castro, W. Porcal, A. Gerpe, M. González and H. Cerecetto, Bioorg. Med. Chem., 18, 795 (2010); doi:10.1016/j.bmc.2009.11.053.
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R.C.F. Jones and J.N. Martin, in eds.: A. Padwa and W.H. Pearson, Nitrones: In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products, John Wiley & Sons, New York, pp. 8-63 (2002).
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P.R. West and G.C. Davis, J. Org. Chem., 54, 5176 (1989); doi:10.1021/jo00282a040.
P.A.S. Smith and S.E. Gloyer, J. Org. Chem., 40, 2504 (1975); doi:10.1021/jo00905a018.
R.W. Murray and M. Singh, J. Org. Chem., 55, 2954 (1990); doi:10.1021/jo00296a073.
(a) J.P. Freeman, J. Org. Chem., 28, 2508 (1963); doi:10.1021/jo01045a003; (b) G.I. Shchukin, I.A. Girgor’ev and L.B. Volodarskii, Chem. Heterocycl. Compd., 26, 409 (1990); doi:10.1007/BF00497211.
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References

E.G. Janzen, Acc. Chem. Res., 4, 31 (1971); doi:10.1021/ar50037a005.

G. Barriga, C. Olea-Azar, E. Norambuena, A. Castro, W. Porcal, A. Gerpe, M. González and H. Cerecetto, Bioorg. Med. Chem., 18, 795 (2010); doi:10.1016/j.bmc.2009.11.053.

R.A. Floyd, K. Hensley, M.J. Forster, J.A. Kelleher-Andersson and P.L. Wood, Mech. Ageing Dev., 123, 1021 (2002); doi:10.1016/S0047-6374(01)00385-2.

K.B.G. Torssell, Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VSH Publishers, New York, pp. 144-768 (1988).

(a) P. Merino, C.R. Chim., 8, 775 (2005); doi:10.1016/j.crci.2005.02.013; (b) M. Lombardo and C. Trombini, Synthesis, 759 (2000); doi:10.1055/s-2000-6269; (c) P. Merino, S. Franco, F.L. Merchan and T. Tejero, Synlett, 442 (2000); doi:10.1055/s-2000-6555.

(a) J. Hamer and A. Macaluso, Chem. Rev., 64, 473 (1964); doi:10.1021/cr60230a006; (b) Y. Inouye, J. Hara and H. Kakisawa, Chem. Lett., 11, 1407 (1980); doi:10.1246/cl.1980.1407.

R.C.F. Jones and J.N. Martin, in eds.: A. Padwa and W.H. Pearson, Nitrones: In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products, John Wiley & Sons, New York, pp. 8-63 (2002).

(a) B.J. Acken, J.A. Warshaw, D.E. Gallis and D.R. Crist, J. Org. Chem., 54, 1743 (1989); doi:10.1021/jo00268a044; (b) P. Merino, P. Pádár, I. Delso, M. Thirumalaikumar, T. Tejero and L. Kovács, Tetrahedron Lett., 47, 5013 (2006); doi:10.1016/j.tetlet.2006.05.114.

R.T. Coutts, K.W. Hindmarsh and G.E. Myers, Can. J. Chem., 48, 2393 (1970); doi:10.1139/v70-400.

S.L. Ioffe, L.M. Makarenkova, V.M. Shitkin, M.V. Kashutina and V.A. Tartakovskii, Bull. Acad. Sci. USSR, Div. Chem. Sci., 22, 212 (1973); doi:10.1007/BF00854170.

(a) E. Bamberger, Ber. Detsch. Chem. Ges., 27, 1548 (1894); doi:10.1002/cber.18940270276; (b) F.J. Alway and M.D. Welsh, J. Am. Chem. Soc., 24, 1052 (1902); doi:10.1021/ja02025a003.

P.R. West and G.C. Davis, J. Org. Chem., 54, 5176 (1989); doi:10.1021/jo00282a040.

P.A.S. Smith and S.E. Gloyer, J. Org. Chem., 40, 2504 (1975); doi:10.1021/jo00905a018.

R.W. Murray and M. Singh, J. Org. Chem., 55, 2954 (1990); doi:10.1021/jo00296a073.

(a) J.P. Freeman, J. Org. Chem., 28, 2508 (1963); doi:10.1021/jo01045a003; (b) G.I. Shchukin, I.A. Girgor’ev and L.B. Volodarskii, Chem. Heterocycl. Compd., 26, 409 (1990); doi:10.1007/BF00497211.

A. Goti, F. Cardona and G. Soldaini, Org. Synth., 81, 204 (2005); Coll. Vol. 11, p. 114-120 (2009); doi:10.15227/orgsyn.081.0204.

M. Prescott, J.P. Larly and D.A. Klein, Microbiology, McGraw-Hill, edn 5 (2002); Microbiologie, De Boeck & Larcier Publishers, French edn 2, pp.809-810 (2003).

J.G. Millar and K.F. Haynes, Methods in Chemical Ecology: Bioassay Methods, Kluwer Academic Publishers, First Printed, vol. 2, pp. 432-433 (1998).

B. Badji, A. Zitouni, F. Mathieu, A. Lebrihi and N. Sabaou, Can. J. Microbiol., 52, 373 (2006); doi:10.1139/w05-132.

(a) P. Laszlo and P. Pennetreau, J. Org. Chem., 52, 2407 (1987); doi:10.1021/jo00388a014; (b) A.W. Johnson, Invitation to Organic Chemistry, Jones and Bartlett Publishers, Sudbury, MA, USA (1999).

Issue

Vol. 28 No. 5 (2016): Vol 28 Issue 5

Synthesis and Microbiological Activities of Novel Acyclic Nitrones

Corresponding Author(s) : Cherifa Mahieddine

Abstract

Keywords

Full Article

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References

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