135508-68-8

Upstream product

• 957-68-6 7-Aminocephalosporanic acid 
• 15690-38-7 (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 29126-13-4 3-hydroxymethyl-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 908093-98-1 diazodiphenylmethane 
• 5935-65-9 Desacetylcephalothin 

Downstream Products

• 142967-18-8 (6R,7R)-3-(4-nitrophenoxycarbonyloxy)methyl-7-(2-thienylacetamido)-Δ³-cephem-4-carboxylic acid 

Relevant academic research and scientific papers

FLUOROGENIC BETA-LACTAMASE SUBSTRATE AND ASSOCIATED DETECTION METHOD

This invention relates to probes for the detection of β-lactamase-type enzymatic activity. In particular, the invention relates to novel fluorogenic substrates for detecting the presence of a catalytically active β-lactamase and a detection method using such substrates.

Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches

We report the synthesis and total NMR characterization of 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid-3-[[[(4″- nitrophenoxy)carbonyl]oxy]-methyl]-8-oxo-7-[(2-thienyloxoacetyl)amino] -diphenylmethyl ester-5-dioxide (5), a new cephalosporin derivative. This compound can be used as the carrier of a wide range of drugs containing an amino group. The preparation of the intermediate product, 5-thia-1-azabicyclo[4.2.0] oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino) pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (6), as well as the synthesis of the antimalarial primaquine prodrug 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl) amino]- 5-dioxide (7) are also described, together with their total 1H- and 13C-NMR assignments.

Conjoint molecules of cephalosporins and aminoglycosides

A general synthetic route to conjoint molecules of cephalosporins and aminoglycosides is described. These molecules were designed as potential substrates for bacterial β-lactamases, enzymes that hydrolyze the β-lactam bond of cephalosporins. Hydrolysis of the β-lactam bond was expected to release the C10-appended aminoglycoside. Since β-lactamases are sequestered in the periplasmic space of gram-negative bacteria, this sequence of events would liberate aminoglycoside inside such bacteria. It is expected that such local delivery of aminoglycosides would circumvent the inherent toxicity of aminoglycosides that occurs during systemic exposure within the mammalian host.

A practical synthetic method for 3-(N,N-disubstituted carbamoyloxy)methyl cephems without generating the Δ2-isomers

E1101, a new oral cephalosporin, has a (N,N-dimethylcarbamoyloxy)methyl group at the C-3 position of the cephem nucleus. The previous methods for manufacturing 3-(N,N-disubstituted carbamoyloxy)methyl cephems generate various amounts of intractable Δ