Synthesis and antibacterial activity of 6- and 7- (2-(5-carboxyimidazole-4-carboxamido)phenylacetamido)-penicillins and cephalosporins.

Yasuda, Naohiko; Iwagami, Hisao; Nakanishi, Eiji; Nakamiya, Teruaki; Sasaki, Yukio; Murata, Tomoki

doi:10.7164/antibiotics.36.242

Cited by 16 publications

(14 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As an acid, the pKa of imidazole is 14.5, making it less acidic than carboxylic acids, phenols, and imides, but slightly more acidic than alcohols [6]. Imidazole derivatives of carboxylic acids or their derivatives can be obtained in good yields by reacting heterocyclic compounds having an aromatic structure, with at least two nitrogen atoms in the ring and at least one hydrogen atom on the ring, with carbon dioxide at elevated temperature in the presence of an acid binding reagent [7][8][9]. 4,5-Imidazoledicarboxylicacid is a useful intermediate for drugs.…”

Section: Imidazolementioning

confidence: 99%

“…The amides which can be readily obtained from 4, 5-imidazoledicarboxylic acid have a stimulating effect on the central nervous system and are also used therapeutically as sedatives. 4, 5-Imidazoledicarboxylic acid is also used for the preparation of 4-aminoimidazole-5-carboxylic acid, an intermediate for purine syntheses, and is furthermore an important building block for semi-synthetic penicillin's and cephalosporins with excellent activity [7]. The background of ligand is relate to the novel Imidazoledicarboxylic acids derivatives, which are useful as antibiotics, cephalon sporanic acid (IV).…”

Section: Imidazolementioning

confidence: 99%

“…The background of ligand is relate to the novel Imidazoledicarboxylic acids derivatives, which are useful as antibiotics, cephalon sporanic acid (IV). Finally, this compound is condensed with 4-pyridineethanesulfonic acid by means of NaI in water at 70°C [7][8][9]. Application of 4, 5-imidazoledicarboxylic acid with SOCl 2 for Synthesis of semi-synthetic penicillin's (Figures 2 and 3).…”

Section: Imidazolementioning

confidence: 99%

“…The discrete metal-organic polygons and polyhedral have been widely studied and continue to be one of the most interesting. Particularly, the zero-dimensional unit with suitable hydrogen-bond donor and particularly antibacterial agents in the treatment of infectious diseases caused by pseudomonas aeruginosa in both human beings and other animals and inter-mediates [7]. 4,5-Imidazoledicarboxylic acids is a bis-bidentate bridging ligand, having two nitrogen and two carboxyl groups and can act both as a multiple proton donor and acceptor as well as, highly accessible to metal ions to build interesting crystals structures [10,11].…”

Section: Supramolecular and Coordination Chemistry Of 4 5-imidazoledmentioning

confidence: 99%

See 3 more Smart Citations

A Review on 4, 5-Imidazoledicarboxylic Acid: Their Chemistry and Coordination Potentials

Dirersa¹

2017

Mod Chem Appl

View full text Add to dashboard Cite

As part of heterocyclic imidazole interest to explore new receptors for anion; 4,5-imidazoledicarboxylic acid and their derivatives have great roles in coordination chemistry. This review, was also update the application and behaviour of 4,5-imidazoledicarboxylic acid (H 3 IMDC) as a potential motif for coordination compound in supramolecular structure activity. H 3 IMDC contains one imidazole NH and two COOH protons which could be donated for hydrogen bonding to the anions. Due to the electronic properties of carboxyl group oxygens, coordination to metal ions can occur in different modes. In situ ligand synthesis is of growing interest as a new approach for the synthesis of coordination polymers. The main reason for interesting of 4,5-imidazoledicarboxylic acid (H 3 IMDC) and its derivatives in coordination polymers of metal-organic framework is because it has six potential donor atoms: two imidazole nitrogens and four carboxylate oxygen atoms, and can remove one to three hydrogen atoms forming H 3-n IMDC n-(n=1,2 or 3) species. The six donors may show various coordination modes and construct beautiful structures. In present review, the chemistry of 4,5-imidazoledicarboxylic acid and its coordination potential in coordination and supramolecular chemistry, which are uses as input for medicinal and drug synthesis, pharmacological actions and as biological activity; where reviewed based on the coordination potentials of imidazole derived heterocyclic molecules in metal-organic frameworks.

show abstract

Section: Imidazolementioning

confidence: 99%

Section: Imidazolementioning

confidence: 99%

Section: Imidazolementioning

confidence: 99%

Section: Supramolecular and Coordination Chemistry Of 4 5-imidazoledmentioning

confidence: 99%

See 2 more Smart Citations

A Review on 4, 5-Imidazoledicarboxylic Acid: Their Chemistry and Coordination Potentials

Dirersa¹

2017

Mod Chem Appl

View full text Add to dashboard Cite

show abstract

“…(1,4,(8)(9)(10). The cefpimizole antimicrobial spectrum most resembles that of cefoperazone and cefpiramide (2,5), both considered to be third-generation cephalosporins.…”

mentioning

confidence: 99%

In vitro comparative antimicrobial activity of cefpimizole against clinical isolates from five medical centers

Jones¹,

Ayers²,

Gavan³

et al. 1985

Antimicrob Agents Chemother

View full text Add to dashboard Cite

Cefpimizole was compared with cefoperazone and cefotaxime against 6,599 clinical bacterial isolates from five medical centers. Cefoperazone and cefotaxime were both more active and provided a greater spectrum of antimicrobial coverage than cefpimizole. Some of the cefpimizole minimum concentrations inhibiting 50% of tested strains were as follows: Citrobacterfreundii and Enterobacter cloacae, 16 ,g/ml; Escherichia coli and KkebsieUla pneumoniae, 2.0 ,ig/ml; Proteus mirabilis, 1.0 ,ug/ml; Pseudomonas aeruginosa, 16 gAg/mi; Staphylococcus spp., 32 ,ug/ml; and the enterococci, >32 jg/ml.

show abstract

Synthesis of novel imidazole‐4,5‐dicarboxylic acid derivatives

Yasuda

1985

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

Synthesis and antibacterial activity of 6- and 7- (2-(5-carboxyimidazole-4-carboxamido)phenylacetamido)-penicillins and cephalosporins.

Cited by 16 publications

References 6 publications

A Review on 4, 5-Imidazoledicarboxylic Acid: Their Chemistry and Coordination Potentials

A Review on 4, 5-Imidazoledicarboxylic Acid: Their Chemistry and Coordination Potentials

In vitro comparative antimicrobial activity of cefpimizole against clinical isolates from five medical centers

Synthesis of novel imidazole‐4,5‐dicarboxylic acid derivatives

Contact Info

Product

Resources

About