DIASTEREOMERIC 7-UREIDOACETYL CEPHALOSPORINS. II 7β-[[[(AMINOCARBONYL)AMINO]-2-THIENYLACETYL] AMINO]-7-METHOXY-3-[[(1-METHYL-1H-TETRAZOL-5-YL)THIO] METHYL]-8-OXO-5-THIA-1-AZABICYCLO [4.2.0] OCT-2-ENE-2- CARBOXYLIC ACID

H. E. APPLEGATE; C. M. CIMARUSTI; J. E. DOLFINI; W. H. KOSTER; M. A. ONDETTI; W. A. SLUSARCHYK; M. G. YOUNG; H. BREUER; U. D. TREUNER

doi:10.7164/antibiotics.31.561

DIASTEREOMERIC 7-UREIDOACETYL CEPHALOSPORINS. II

7β-[[[(AMINOCARBONYL)AMINO]-2-THIENYLACETYL] AMINO]-7-METHOXY-3-[[(1-METHYL-1H-TETRAZOL-5-YL)THIO] METHYL]-8-OXO-5-THIA-1-AZABICYCLO [4.2.0] OCT-2-ENE-2- CARBOXYLIC ACID

H. E. APPLEGATE, C. M. CIMARUSTI, J. E. DOLFINI, W. H. KOSTER, M. A. ONDETTI, W. A. SLUSARCHYK, M. G. YOUNG, H. BREUER, U. D. TREUNER

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JOURNAL FREE ACCESS

1978 Volume 31 Issue 6 Pages 561-569

DOI https://doi.org/10.7164/antibiotics.31.561

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Abstract

The synthesis and antibacterial activity in vitro of 7-methoxylated cephalosporins having a thienylureidoacetyl or a thienylglycyl C-7 side-chain are described. Acylation of 7β-amino-7- methoxycephems with a novel 2-aminooxazolone hydrochloride under neutral conditions gave the thienylureidoacetyl derivatives in good yield with retention of configuration. 7β-[[D-[(Aminocarbonyl)amino]-2-thienylacetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio] methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylica cid sodium salt (SQ 14, 359) was found to have a broad-spectrum of antibacterial activity in vitro, particularly against β-lactamase-producing organisms.

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