Abstract

Several new 4-diazopyrazole derivatives 6a-g and 9a-c were obtained by the reaction of 1-(R-substituted phenyl)-3-(1,3-dimethyl-1H-pyrazol-5-yl)ureas 5a-g and N-(1,3-dimethyl-1H-pyrazol-5-yl)-2-(R-substituted phenyl)acetamides 8a-c respectively with a sevenfold excess of nitrous acid in acetic acid solution. The compounds were assayed for their activity against the Staphylococcus aureus reference strains ATCC 25923, ATCC 29213 and ATCC 6538, as well as six veterinary strains. The best anti-staphylococcal profile was showed by [(R-substituted phenyl)acetyl](4-diazonio-1,3-dimethyl-1H-pyrazol-5-yl)azanides 9a,c. The compound 9c was also able at 3.1 µg mL-1 to inhibit of 45.7% the biofilm formation of the strains S.aureus ATCC 29213.
Lingua originaleEnglish
pagine (da-a)64-71
Numero di pagine8
RivistaEuropean Journal of Medicinal Chemistry
Volume58
Stato di pubblicazionePublished - 2012

Fingerprint

Acetamides
Nitrous Acid
Biofilms
Acetic Acid
Urea
Staphylococcus aureus
Derivatives

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cita questo

@article{8cc8f6c477bf4e0f84ff74e3985b16aa,
title = "Synthesis and anti-staphylococcal activity of new 4-diazopyrazole derivatives",
abstract = "Several new 4-diazopyrazole derivatives 6a-g and 9a-c were obtained by the reaction of 1-(R-substituted phenyl)-3-(1,3-dimethyl-1H-pyrazol-5-yl)ureas 5a-g and N-(1,3-dimethyl-1H-pyrazol-5-yl)-2-(R-substituted phenyl)acetamides 8a-c respectively with a sevenfold excess of nitrous acid in acetic acid solution. The compounds were assayed for their activity against the Staphylococcus aureus reference strains ATCC 25923, ATCC 29213 and ATCC 6538, as well as six veterinary strains. The best anti-staphylococcal profile was showed by [(R-substituted phenyl)acetyl](4-diazonio-1,3-dimethyl-1H-pyrazol-5-yl)azanides 9a,c. The compound 9c was also able at 3.1 µg mL-1 to inhibit of 45.7{\%} the biofilm formation of the strains S.aureus ATCC 29213.",
keywords = "4-diazopyrazoles, anti-biofilm activity, anti-staphylococcal activity",
author = "Fabiana Plescia and Raimondi, {Maria Valeria} and Demetrio Raffa and Cusimano, {Maria Grazia} and Cascioferro, {Stella Maria} and Gabriella Cancemi and Benedetta Maggio and Domenico Schillaci and Giuseppe Daidone and Maria Vitale",
year = "2012",
language = "English",
volume = "58",
pages = "64--71",
journal = "European Journal of Medicinal Chemistry",
issn = "0223-5234",
publisher = "Elsevier Masson SAS",

}

TY - JOUR

T1 - Synthesis and anti-staphylococcal activity of new 4-diazopyrazole derivatives

AU - Plescia, Fabiana

AU - Raimondi, Maria Valeria

AU - Raffa, Demetrio

AU - Cusimano, Maria Grazia

AU - Cascioferro, Stella Maria

AU - Cancemi, Gabriella

AU - Maggio, Benedetta

AU - Schillaci, Domenico

AU - Daidone, Giuseppe

AU - Vitale, Maria

PY - 2012

Y1 - 2012

N2 - Several new 4-diazopyrazole derivatives 6a-g and 9a-c were obtained by the reaction of 1-(R-substituted phenyl)-3-(1,3-dimethyl-1H-pyrazol-5-yl)ureas 5a-g and N-(1,3-dimethyl-1H-pyrazol-5-yl)-2-(R-substituted phenyl)acetamides 8a-c respectively with a sevenfold excess of nitrous acid in acetic acid solution. The compounds were assayed for their activity against the Staphylococcus aureus reference strains ATCC 25923, ATCC 29213 and ATCC 6538, as well as six veterinary strains. The best anti-staphylococcal profile was showed by [(R-substituted phenyl)acetyl](4-diazonio-1,3-dimethyl-1H-pyrazol-5-yl)azanides 9a,c. The compound 9c was also able at 3.1 µg mL-1 to inhibit of 45.7% the biofilm formation of the strains S.aureus ATCC 29213.

AB - Several new 4-diazopyrazole derivatives 6a-g and 9a-c were obtained by the reaction of 1-(R-substituted phenyl)-3-(1,3-dimethyl-1H-pyrazol-5-yl)ureas 5a-g and N-(1,3-dimethyl-1H-pyrazol-5-yl)-2-(R-substituted phenyl)acetamides 8a-c respectively with a sevenfold excess of nitrous acid in acetic acid solution. The compounds were assayed for their activity against the Staphylococcus aureus reference strains ATCC 25923, ATCC 29213 and ATCC 6538, as well as six veterinary strains. The best anti-staphylococcal profile was showed by [(R-substituted phenyl)acetyl](4-diazonio-1,3-dimethyl-1H-pyrazol-5-yl)azanides 9a,c. The compound 9c was also able at 3.1 µg mL-1 to inhibit of 45.7% the biofilm formation of the strains S.aureus ATCC 29213.

KW - 4-diazopyrazoles

KW - anti-biofilm activity

KW - anti-staphylococcal activity

UR - http://hdl.handle.net/10447/78370

M3 - Article

VL - 58

SP - 64

EP - 71

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

SN - 0223-5234

ER -