73443-60-4

Usage

Uses

Used in Pharmaceutical Industry:
7β-[(Z)-2-(2-Aminothiazol-4-yl)-2-(1-carboxy-1-Methylethoxyimino)acetamido]-3-acetoxyMethyl-3-cephem-4-carboxylic Acid is used as an antibacterial agent for the development of new antibiotics. Its application is based on its ability to combat bacterial infections by inhibiting the growth and proliferation of bacteria, making it a valuable asset in the fight against antibiotic-resistant strains.
Used in Research and Development:
In the field of scientific research, 7β-[(Z)-2-(2-AMinothiazol-4-yl)-2-(1-carboxy-1-MethylethoxyiMino)acetaMido]-3-acetoxyMethyl-3-cepheM-4-carboxylic Acid can be used as a starting material or a key intermediate for the synthesis of novel antibiotics with improved properties, such as enhanced efficacy, reduced side effects, or targeted action against specific bacterial strains. Its unique chemical structure allows researchers to explore new avenues in antimicrobial drug design and development.
Used in Drug Delivery Systems:
Similar to gallotannin, 7β-[(Z)-2-(2-Aminothiazol-4-yl)-2-(1-carboxy-1-Methylethoxyimino)acetamido]-3-acetoxyMethyl-3-cephem-4-carboxylic Acid can also be incorporated into drug delivery systems to improve its bioavailability, delivery, and therapeutic outcomes. This may involve the use of various organic and metallic nanoparticles as carriers, which can help to enhance the compound's effectiveness in treating bacterial infections.

Upstream product

• 263154-28-5 (6R,7R)-3-Acetoxymethyl-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-1-tert-butoxycarbonyl-1-methyl-ethoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 27266-61-1 benzhydryl 7-aminocephalosporanate 
• 957-68-6 7-Aminocephalosporanic acid 
• 66339-00-2 ethyl (Z)-2-(2-triphenylmethylaminothiazol-4-yl)-2-(hydroxyimino)acetate hydrochloride 
• 68672-66-2 (Z)-2-(1-t-butoxycarbonyl-1-methylethoxyimino)-2-[2-(triphenylmethylamino)thiazol-4-yl]acetic acid 
• 68672-65-1 imino-2 Z (tritylamino-2 thiazolyl-4)-2 acetate d'ethyle 
• 86299-47-0 (Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid 
• 68672-67-3 ester de tert-butylique de l'acide (acetoxy methyl)-3(<<-imino-2 Z (tritylamino-2 thiazolyl-4)-2>-acetyl>-amino)-7 β cepheme-3 carboxylique-4 

Relevant academic research and scientific papers

Antimicrobial effects of novel siderophores linked to β-lactam antibiotics

As a strategy to increase the penetration of antibiotic drugs through the outer membrane of Gram-negative pathogens, facilitated transport through siderophore receptors has been frequently exploited. Hydroxamic acids, catechols, or very close isosteres of catechols, which are mimics of naturally occurring siderophores, have been used successfully as covalently linked escorting moieties, but a much wider diversity of iron binding motifs exists. This observation, coupled to the relative lack of specificity of siderophore receptors, prompted us to initiate a program to identify novel, noncatechol siderophoric structures. We screened over 300 compounds for their ability to (1) support growth in low iron medium of a Pseudomonas aeruginosa siderophore biosynthesis deletion mutant, or (2) compete with a bactericidal siderophore-antibiotic conjugate for siderophore receptor access. From these assays we identified a set of small molecules that fulfilled one or both of these criteria. We then synthesized these compounds with functional groups suitable for attachment to both monobactam and cephalosporin core structures. Siderophore-β-lactam conjugates then were tested against a panel of Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus strains. Although several of the resultant chimeric compounds had antimicrobial activity approaching that of ceftazidime, and most compounds demonstrated very potent activity against their cellular targets, only a single compound was obtained that had enhanced, siderophore-mediated antibacterial activity. Results with tonB mutants frequently showed increased rather than decreased susceptibilities, suggesting that multiple factors influenced the intracellular concentration of the drugs. (C) 2000 Elsevier Science Ltd.

3-substituted cephem compounds

The present invention relates to novel cephalosporins of the formula (I); STR1 wherein, R1 represents a C1 ?C4 alkyl group or STR2 wherein, R2 and R3, independently, represent hydrogen or a C1 ?C3 alkyl group and R4 represents hydrogen or a C1 ?C4 alkyl group; R1a represents hydrogen or an amino-protecting group; Q represents CH or N; and the formula STR3 represents a saturated or unsaturated heterocyclic group which contains 1 to 4 nitrogen atoms of which one is substituted with an amino group to form quaternary ammonium, and oxygen or sulfur, or a fused heterocyclic group thereof formed together with a substituted or unsubstituted benzene or an optional heterocyclic group, or a pharmaceutically acceptable salt thereof, to processes for preparing the same and to a pharmaceutical composition containing the same as an active ingredient. The compounds(1) according to the invention exhibit potent antibacterial activity and broad antibacterial spectrum against the Gram-positive strains including Staphylococcus as well as Gram-negative strains including Pseudomonas, and, therefore, are expected to be very useful in treatment of various diseases caused by bacterial infection in human beings and animals.

Cephalosporin antibiotics

Cephalosporin antibiotics of general formula STR1 (wherein Ra and Rb, which may be the same or different, each represent a C1-4 alkyl group, or together with the carbon atom to which they are attached form a C3-7 cycloalkylidene group and R1 represents a C1-4 alkyl group) exhibit broad spectrum antibiotic activity, the activity being unusually high against gram-negative organisms such as strains of Pseudomonas organisms. Particularly effective compounds of formula (I) are (6R,7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-(2-methylpyrazolium-1-ylmethyl)ceph-3-em-4-carboxylate and (6R,7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-[(1-carboxycyclobut-1-oxyimino)acetamido]-3-(2-methylpyrazolium-1-ylmethyl)]ceph-3-em-4-carboxylate. The invention also includes the non-toxic salts and non-toxic metabolically labile esters of compounds of formula (I), compositions containing the antibiotic compounds of the invention, and methods for combatting bacterial infections utilizing the antibiotics.