Termolecular One‐Pot Synthesis of Symmetrical Azines of 4‐Acetyl‐3‐arylsydnones. Hydrazone and Azine Derivatives of 4‐Acetyl‐3‐arylsydnones, Their Spectral Characterization and Biological Properties.

Shinge, Prashant S.; Mallur, Shanta G.; Badami, Bharati V.

doi:10.1002/chin.200618227

“…In 2005, Shinge et al reported the reaction of 4-acetyl-3-arylsydnone derivatives [11] with hydrazine leading to the formation of hydrazones 1 and dimers 2 in good yields and the evaluation of their antimicrobial activities against various Gram-negative bacteria and fungi (Table 1). Determination of the antifungal activity of derivatives 2 led to similar results that their parent monomers 1 (Table 1, derivatives 1e-1f and 2e-2f) whereas weaker activities were encountered against bacteria.…”

Section: ) R Is a Hydrogenmentioning

confidence: 99%

Frontiers in Anti-Infective Drug Discovery: Volume 9

2021

Frontiers in Anti-Infective Drug Discovery

0

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Antimicrobial resistance of Gram-negative bacteria is a major concern and no new classes of antibiotics that are effective against this type of bacteria have been discovered since the 1960s. During the last decades, multiple approaches have been developed to combat such a bacterial resistance. However, the combination of antibiotic resistance mechanisms by bacteria and the limited number of effective antibiotics available, decreases the number of the interventions for the treatment of current bacterial infections. The solution to emerging antibiotic resistance will likely involve new therapies or new classes of antibacterial agents. For a few years now, there was a real interest in the design and synthesis of hydrazones possessing an azometine -NHN=CH-proton and constituting an important class of compounds for new drugs development as anticonvulsants, antidepressants, antitumoral agents. In this context, the design and antimicrobial evaluation of hydrazone derivatives has constituted one of the new strategies developed to fight bacterial resistance. As pointed out the range of biological activities is very broad, and this review will deal exclusively with the synthesis and use of hydrazones as antimicrobial agents and will not cover the other biological properties already well depicted in literature. Thus, we will report herein the scope and limitation of such an approach providing numerous examples demonstrating structure-activity relationships and potent interesting antimicrobial activities against both fungi, Gram-positive and/or Gram-negative bacteria.

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“…48 Procedure for the Synthesis of 4-Acetyl-3-arylsydnones (2a−d). 49 To a suspension of 5.20 g (0.0369 mol) of phosphorous pentoxide in dry xylene (20 mL) was added 2.00 g (0.0123 mol) of 3-arylsydnones 1a−d in a two-necked RB flask equipped with a reflux condenser with a calcium chloride drying tube. The stirred mixture was heated to reflux on a water bath.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…Procedure for the Synthesis of 1-(3-Arylsydnon-4yl)ethylidene)-2-phenylhydrazines (4a−l). 49 4-Acetyl-3arylsydnones 2a−d (1.0 g, 0.005 mol) were dissolved in ethanol (10 mL), and about 3−4 drops of acetic acid were added. Aryl hydrazines 3a−c (0.50 mL, 0.0049 mol) were then added, and the reaction mixture was refluxed for 2 h. The progress of the reaction was monitored by TLC, and after completion of the reaction, the separated solid was filtered, dried, and recrystallized from ethanol to obtain the compounds 4a−l.…”

Section: ■ Conclusionmentioning

confidence: 99%

Serendipitous Formation of 2H-Pyrazolo[3,4-d]pyridazin-7(6H)-ones from 3-Arylsydnones

Kumbar

¹

,

Shaikh

²

,

Kamble

³

et al. 2019

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Fused nitrogen heterocyclesnamely, pyrazolo[3,4- d ]pyridazin-7(6 H )-ones have been obtained by exploiting the 1,3-dipolar nature of N -arylsydnones, from hydrazones of 3-aryl-4-acetylsydnones via the Vilsmeier–Haack strategy. Facile intramolecular nucleophilic addition followed by CO 2 elimination under reflux or upon microwave irradiation was presented. Plausible mechanisms for the formation of the title compounds are proffered. Structure confirmatory evidence came from single-crystal X-ray crystallography.

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Frontiers in Anti-Infective Drug Discovery Volume 6

2017

0

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Antimicrobial resistance of Gram-negative bacteria is a major concern and no new classes of antibiotics that are effective against this type of bacteria have been discovered since the 1960s. During the last decades, multiple approaches have been developed to combat such a bacterial resistance. However, the combination of antibiotic resistance mechanisms by bacteria and the limited number of effective antibiotics available, decreases the number of the interventions for the treatment of current bacterial infections. The solution to emerging antibiotic resistance will likely involve new therapies or new classes of antibacterial agents. For a few years now, there was a real interest in the design and synthesis of hydrazones possessing an azometine -NHN=CH-proton and constituting an important class of compounds for new drugs development as anticonvulsants, antidepressants, antitumoral agents. In this context, the design and antimicrobial evaluation of hydrazone derivatives has constituted one of the new strategies developed to fight bacterial resistance. As pointed out the range of biological activities is very broad, and this review will deal exclusively with the synthesis and use of hydrazones as antimicrobial agents and will not cover the other biological properties already well depicted in literature. Thus, we will report herein the scope and limitation of such an approach providing numerous examples demonstrating structure-activity relationships and potent interesting antimicrobial activities against both fungi, Gram-positive and/or Gram-negative bacteria.

show abstract

Termolecular One‐Pot Synthesis of Symmetrical Azines of 4‐Acetyl‐3‐arylsydnones. Hydrazone and Azine Derivatives of 4‐Acetyl‐3‐arylsydnones, Their Spectral Characterization and Biological Properties.

Cited by 4 publications

References 2 publications

Frontiers in Anti-Infective Drug Discovery: Volume 9

Frontiers in Anti-Infective Drug Discovery: Volume 9

Serendipitous Formation of 2H-Pyrazolo[3,4-d]pyridazin-7(6H)-ones from 3-Arylsydnones

Frontiers in Anti-Infective Drug Discovery Volume 6

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