Antibacterial nitrofuran derivatives. 2. 5-Nitro-2-furaldehyde aminoacethydrazones

Massarani, E; Nardi, D; Tajana, A; Degen, Lukas

doi:10.1021/jm00289a019

Cited by 30 publications

(11 citation statements)

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“…[26,27] Salicylaldehyde benzoylhydrazone and analogous aroyl hydrazones have been studied as chelating agents to mobilize iron for iron-overload therapy, [28,29] and their transition metal complexes possess antitumour properties. [30][31][32][33] Many hydrazones and their transition metal complexes are used as antibacterial, antiviral, antitubercular, [34] antimycobacterial [35] and antifungal agents, [36,37] and in industry they are employed as plasticizers [38] and catalysts. [39][40][41] N-acyl and N-aroyl hydrazones of salicylaldehyde [42][43][44][45][46] (Figure 3) can form 2:2 copper(II) complexes as tridentate ligands with the phenolate oxygen, azomethine nitrogen and enolimide oxygen atoms defining the binding site.…”

Section: Cumentioning

confidence: 99%

Salicylaldehyde Hydrazones: Buttressing of Outer-Sphere Hydrogen-Bonding and Copper Extraction Properties

et al. 2017

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Salicylaldehydes hydrazones are weaker copper extractants than their oxime derivatives which are used in hydrometallurgical processes to recover approximately 20% of the world's copper. Their strength, based on the extraction equilibrium constant Ke, can be increased by nearly three orders of magnitude by incorporating electron-withdrawing or hydrogen bond acceptor groups (X) ortho to the phenolic OH group of the salicylaldehyde unit. DFT calculations suggest that the effects of the 3-X substituents arise from a combination of their influence on the acidity of the phenol in the pHdependent equilibrium:and on their ability to "buttress" interligand hydrogen bonding by interacting with the hydrazone N-H donor group. X-ray crystal structure determination and computed structures indicated that in both the solid state and the gas phase, coordinated hydrazone groups are less planar than coordinated oximes and this has an adverse effect on intramolecular hydrogen bond formation to the neighbouring phenolate oxygen atoms.

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Section: Cumentioning

confidence: 99%

Salicylaldehyde Hydrazones: Buttressing of Outer-Sphere Hydrogen-Bonding and Copper Extraction Properties

et al. 2017

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“…In preceding studies the in vitro activities of a new water-soluble ni trofuran derivative (nifurpipone, Rec 15-0122) were described [1,2,7,8]. The present paper reports the data obtained from a series of in vivo chemotherapeutic tests.…”

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confidence: 93%

Antimicrobial Activity of 5-Nitro-2-Furaldehyde-N′-Methyl-N-Piperazino-Acethydrazone, a New Hydrosoluble Nitrofuran Derivative

Degen¹,

Salvaterra²,

Vella³

et al. 1973

Chemotherapy

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The in vivo activity of Rec 15-0122 (nifurpipone), a new water-soluble nitrofuran derivative, has been investigated in some standardized infections. The drug, after oral administration, is active in mice in systemic infections with Streptococcus pyogenes and Salmonella typhimurium and in local infections with Staphylococcus aureus. In experimental urinary tract infections of rats nifurpipone prevents ascending infection and stone formation.

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“…In our laboratories during the last years [7,8] a series of 5-nitro-2-furaldehyde monoalkylaminoacethydrazones (I), of dialkylaminoacethydrazones (II) and of N'-substituted-N-piperazino-acethydrazones (III) were synthesized. All compounds were tested for antimicrobial activity in vitro against a representative series of micro-organisms.…”

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confidence: 99%

Antimicrobial Activity of a Series of New 5-Nitro-2-fluraldehyde Aminoacethydrazones

Degen¹,

Salvaterra²,

Vella³

et al. 1972

Chemotherapy

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A series of 5-nitro-2-furaldehyde aminoacethydrazones, synthesized in our laboratories are screened in vitro and in vivo for antibacterial activity. Because of its good antibacterial activity against gram-negative and gram-positive organisms, its good absorption and its exretion in high urinary levels in active form, the 5-nitro-2-furaldehyde 4’-methylpiperazinoacethydrazone (Rec. 15-0122, nifurpipone) was selected for further studies.

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Antibacterial nitrofuran derivatives. 2. 5-Nitro-2-furaldehyde aminoacethydrazones

Cited by 30 publications

References 1 publication

Salicylaldehyde Hydrazones: Buttressing of Outer-Sphere Hydrogen-Bonding and Copper Extraction Properties

Salicylaldehyde Hydrazones: Buttressing of Outer-Sphere Hydrogen-Bonding and Copper Extraction Properties

Antimicrobial Activity of 5-Nitro-2-Furaldehyde-N′-Methyl-N-Piperazino-Acethydrazone, a New Hydrosoluble Nitrofuran Derivative

Antimicrobial Activity of a Series of New 5-Nitro-2-fluraldehyde Aminoacethydrazones

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