73443-60-4

Basic information

• Product Name: 7β-[(Z)-2-(2-AMinothiazol-4-yl)-2-(1-carboxy-1-MethylethoxyiMino)acetaMido]-3-acetoxyMethyl-3-cepheM-4-carboxylic Acid
• Synonyms: 7β-[(Z)-2-(2-AMinothiazol-4-yl)-2-(1-carboxy-1-MethylethoxyiMino)acetaMido]-3-acetoxyMethyl-3-cepheM-4-carboxylic Acid;72-[(Z)-2-(2-Aminothiazol-4-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic Acid
• CAS NO: 73443-60-4
• Molecular Formula: C₁₉H₂₁N₅O₉S₂
• Molecular Weight: 527.52814
• Product Categories: Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 73443-60-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Dimethylsulfoxide
• CAS DataBase Reference: 7β-[(Z)-2-(2-AMinothiazol-4-yl)-2-(1-carboxy-1-MethylethoxyiMino)acetaMido]-3-acetoxyMethyl-3-cepheM-4-carboxylic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7β-[(Z)-2-(2-AMinothiazol-4-yl)-2-(1-carboxy-1-MethylethoxyiMino)acetaMido]-3-acetoxyMethyl-3-cepheM-4-carboxylic Acid(73443-60-4)
• EPA Substance Registry System: 7β-[(Z)-2-(2-AMinothiazol-4-yl)-2-(1-carboxy-1-MethylethoxyiMino)acetaMido]-3-acetoxyMethyl-3-cepheM-4-carboxylic Acid(73443-60-4)

Safety Data

• Hazardous Substances Data: 73443-60-4(Hazardous Substances Data)

Usage

Description

7β-[(Z)-2-(2-Aminothiazol-4-yl)-2-(1-carboxy-1-Methylethoxyimino)acetamido]-3-acetoxyMethyl-3-cephem-4-carboxylic Acid is a complex organic compound with a unique chemical structure. It is a derivative of cefotaxime, a well-known antibiotic, and possesses antibacterial properties. 7β-[(Z)-2-(2-AMinothiazol-4-yl)-2-(1-carboxy-1-MethylethoxyiMino)acetaMido]-3-acetoxyMethyl-3-cepheM-4-carboxylic Acid is characterized by its light brown solid appearance and is potentially useful in the pharmaceutical industry due to its antimicrobial activity.

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, this compound 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

• 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 
• 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 
• 86299-47-0 (Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid 
• 68672-65-1 imino-2 Z (tritylamino-2 thiazolyl-4)-2 acetate d'ethyle 
• 68672-66-2 (Z)-2-(1-t-butoxycarbonyl-1-methylethoxyimino)-2-[2-(triphenylmethylamino)thiazol-4-yl]acetic acid 
• 66339-00-2 ethyl (Z)-2-(2-triphenylmethylaminothiazol-4-yl)-2-(hydroxyimino)acetate hydrochloride 

Relevant articles and documents

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.

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.