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Semisynthetic beta-lactam antibiotics. IV. Synthesis and antibacterial activity of 7 beta-[2-(hetero aromatic methoxyimino)-2-(2-aminothiazol-4-yl)acetamido]cephalosporins. 1988

M Arimoto, and S Yokohama, and M Sudou, and Y Ichikawa, and T Hayano, and H Tagawa, and M Furukawa
Research Institute, Daiichi Seiyaku Co., Ltd., Tokyo, Japan.

A series of 7 beta-[2-(hetero aromatic methoxyimino)-2-(2-aminothiazol-4-yl)acetamido]- cephalosporins have been synthesized and bacteriologically evaluated. Several substances in this series showed exceptional in vitro activity, especially those with a five-membered hetero aromatic substituent moiety at the 7-position and a quaternary ammonium group as the 3-function of the cephem nucleus. The most active derivative, 7 beta-[2-(imidazol-4-ylmethoxyimino)-2-(2-aminothiazol-4-yl)a cetamido]-3-(pyridiniomethyl)ceph-3-em-4-carboxylate (13a) was the most evenly balanced with respect to activity against Gram-positive and Gram-negative bacteria. Furthermore, 13 was stable to various types of beta-lactamases and had high affinities for penicillin binding protein-3 and -1Bs of both Escherichia coli and Pseudomonas aeruginosa.

UI MeSH Term Description Entries
D002511 Cephalosporins A group of broad-spectrum antibiotics first isolated from the Mediterranean fungus ACREMONIUM. They contain the beta-lactam moiety thia-azabicyclo-octenecarboxylic acid also called 7-aminocephalosporanic acid. Antibiotics, Cephalosporin,Cephalosporanic Acid,Cephalosporin,Cephalosporin Antibiotic,Cephalosporanic Acids,Acid, Cephalosporanic,Acids, Cephalosporanic,Antibiotic, Cephalosporin,Cephalosporin Antibiotics
D004355 Drug Stability The chemical and physical integrity of a pharmaceutical product. Drug Shelf Life,Drugs Shelf Lives,Shelf Life, Drugs,Drug Stabilities,Drugs Shelf Life,Drugs Shelf Live,Life, Drugs Shelf,Shelf Life, Drug,Shelf Live, Drugs,Shelf Lives, Drugs
D001419 Bacteria One of the three domains of life (the others being Eukarya and ARCHAEA), also called Eubacteria. They are unicellular prokaryotic microorganisms which generally possess rigid cell walls, multiply by cell division, and exhibit three principal forms: round or coccal, rodlike or bacillary, and spiral or spirochetal. Bacteria can be classified by their response to OXYGEN: aerobic, anaerobic, or facultatively anaerobic; by the mode by which they obtain their energy: chemotrophy (via chemical reaction) or PHOTOTROPHY (via light reaction); for chemotrophs by their source of chemical energy: CHEMOLITHOTROPHY (from inorganic compounds) or chemoorganotrophy (from organic compounds); and by their source for CARBON; NITROGEN; etc.; HETEROTROPHY (from organic sources) or AUTOTROPHY (from CARBON DIOXIDE). They can also be classified by whether or not they stain (based on the structure of their CELL WALLS) with CRYSTAL VIOLET dye: gram-negative or gram-positive. Eubacteria
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

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