Abstract
The quaternary ammonium cephalosporin derivatives were prepared with various pyridines substituted at the 3 or/and 4 position. Theirin vitro antibacterial activities were determined and substituent effect on pyridine nucleus was studied. Preparation of substituted pyridines are also described.
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References Cited
Ansari, M. A., Oxidation Reaction of 2-& 4-Hydroxy Pyridines.Ind. J. Chem., 24B, 972–973 (1985).
Arnould, J. C., Bertrandie, A., Bird, T. C., and Bouchrot, D., Synthesis and Structure-Activity Relationship of Cephalosporins with C-3′ Catechol containing Residues.J. Med. Chem., 35, 2631–2642 (1992).
Bobbitt, J. M. and Daniel, A. S., Synthesis of Isoquinoline Alkaloids. The Synthesis and Reactions of 4-Methyl-3-pyridinecarboxaldehyde and other 4-Methyl-3-substituted Pyridines.J. Org. Chem., 25, 560–564 (1960).
Brown, R. F., Kinnick, M. D., Vasileff, R. T., Counter, F. T., Davidson, E. D., Ensminger, P. W., Eudaly, J. A., Kasher, J. S., Katner, A. S., Koehler, R. E., Kurz, K. D., Lindstrom, T. D., Lunn, W. H. W., Preston, D. A., Ott, J. L., Quay, J. F., Shadle, J. K., Steinberg, A. I., Stucky, J. F., Swartzendruber, J. K., Turner, J. R., Webber, J. A., Wright, W. E., Zimmerman, K. A., Synthesis and Biological Evaluation of a Series of Parenteral 3′-Quaternary Ammonium Cephalosporins.J. Med. Chem., 33, 2114–2121 (1990).
Comins, D. L., and Stroud, E. D., Synthesis of 4-Alkyl-3-pyridinols from 3-Benzyloxypyridine.J. Heterocyclic Chem., 22, 1419–1420 (1985).
David, C. C., Jones, R. H., Kabir, H. and Lythgoe, D. J., Process Development of the PDEInhibitor 3-(Cyclo-pentyloxy)-N-(3,5-dichlo-ropyrid-4-yl)-4-methoxybenzamide.Organic Process Research & Development, 2, 157–168 (1998).
Eggers, L. and Grahn, W., 4-Alkyl-& 4-Benzyl substituted 3,3′-Oxybispyridines.Synthesis, 763–768 (1996).
Ejima, A., Hayano, T., Ebata, T., and Nagahara, T., Synthesis and Antimicrobial Activity of Cephalosporins with a Pyridium Substituent carrying a 5-Membered Heterocycle at the C-3 position.J. Antibiotics, 40, 43–48 (1986).
Erdtman, H., Haglid, F., Welling, S. and Euler, U. S., Synthetic analogues ofnicotine.Acta. Chem. Scand., 117, 1717–1726 (1963).
Hashiyama, T., Arakawa, H. and Wagatsuma, M., A facile access to 3-Cephems by employing novel Lewis acid mediated Reaction.Heterocycles, 47, 121–124 (1998).
Katner, A. S. and Brown, R. F., A Novel Preparation of Thiazolo[5,4-c] pyridines and the Synthesis of some Imidazo[4,5-c] pyridines and Oxazole[4,5-c] pyridines.J. Heterocyclic Chem., 27, 563–566 (1990).
Kuthan, H., Musil, L. and Jehlicka, V., The use of Dipole Moment in the Conformational Analysis of Nicotinic Acid Derivatives.Collection Czechoslov Chem. Commun., 42, 283–291 (1977).
Miah, M. A. J. and Snieckus, V., Directed Ortho Metalation ofO-Pyridylcrabamates. Regiospecific Entries into Poyl substituted PyridineJ. Org. Chem., 50, 5436–5438 (1985).
Sugiyama, I., Komatsu, Y. and Yamauchi, H., Synthesis and Structure-Activity Relationships of a new Series of Cephalosporins, E1040 and Related Compounds.J. Antibiotics, 45, 103–112 (1992).
Taylor, E. C. and Crovetti, A. J., Pyridine-1-oxides. II. A New Synthesis of Ricinine.J. Am. Chem. Soc., 78, 214–217 (1956).
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Chung, I.H., Kim, C.S., Seo, J.H. et al. Synthesis andin vitro antibacterial activity of C-3′ pyridinium cephalosporin derivatives. Arch Pharm Res 22, 391–397 (1999). https://doi.org/10.1007/BF02979063
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DOI: https://doi.org/10.1007/BF02979063