Syntheses of Aromatic Substituted Hydrazino-thiazole Derivatives to Clarify Structural Characterization and Antioxidant Activity between 3-Arylsydnonyl and Aryl Substituted Hydrazino-thiazoles

Shih, Ming Chang; Su, Yu-Sheng; Wu, Cheng‐Ling

doi:10.1248/cpb.55.1126

Cited by 57 publications

(30 citation statements)

References 26 publications

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“…On the other hand, sydnones bearing 4-oxothiazolidine (LIII) were less active. The absence of N-H group rendered the latter to be a weak scavenger [78,79]. …”

Section: Antioxidant Activitymentioning

confidence: 99%

Mesoionic Sydnone: A Review in Their Chemical and Biological Properties

Abdualkader

Taher

Yusoff

2017

Int J Pharm Pharm Sci

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Various literature sources have documented sydnones as important molecules with exclusive chemical properties and a wide spectrum of bioactivities. Sydnone can be defined as a five-membered pseudo-aromatic heterocyclic molecule. Classically, 1,2,3-oxadiazole forms the main skeleton of sydnone. The molecule has delocalized balanced positive and negative charges. The five annular atoms share the positive charge and the enolate-like exocyclic oxygen atom bears the negative charge. The hydrogen atom at the position C4 was proved to have acidic and nucleophilic functionalities making the sydnone ring reactive towards electrophilic reagents. These unique chemical features enable sydnones to interact with biomolecules resulting in important therapeutic effects like anticancer, antidiabetic, antimicrobial, antioxidant and anti-inflammatory. Consequently, we aim from the current article to review the available chemical and pharmacological information on sydnone and its derivatives.

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“…On the other hand, sydnones bearing 4-oxothiazolidine (LIII) were less active. The absence of N-H group rendered the latter to be a weak scavenger [78,79]. …”

Section: Antioxidant Activitymentioning

confidence: 99%

Mesoionic Sydnone: A Review in Their Chemical and Biological Properties

Abdualkader

Taher

Yusoff

2017

Int J Pharm Pharm Sci

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“…Subsequent base-catalyzed methylation of the sulfur atom with iodomethane resulted in intermediate 3 (Scheme 2). [32,33] Dropwise addition of bromine in dichloromethane to a solution of 4-fluoroacetophenone 4 in dichloromethane afforded bromoacetophenone 5.…”

Section: Chemistrymentioning

confidence: 99%

“…Compounds 2, 3, and 5 were prepared according to published data. [32][33][34] N-Benzylidene-4-(4-fluorophenyl)-2-methylthio-1H-imidazol-1-amine (6): A mixture of 3 (11.81 g, 61.1 mmol), 5 (13.261 g, 61.1 mmol), NaHCO 3 (15.4 g, 183 mmol), and CH 3 CN (70 mL) was heated while stirring at 75 8C for 3 h. During this period the orange solution turned into a suspension with a fawn precipitate. After cooling to room temperature, the solids were filtered and washed with cold CH 3 CN.…”

Section: Chemical Analysismentioning

confidence: 99%

Synthesis and Biological Testing of N‐Aminoimidazole‐Based p38α MAP Kinase Inhibitors

et al. 2010

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The p38 mitogen-activated protein (MAP) kinase alpha plays a central role in the regulation of cellular responses such as differentiation, proliferation, apoptosis, and inflammation. Inhibition of p38 results in decreased synthesis of pro-inflammatory cytokines. To date, diverse p38alpha inhibitors are in phase II clinical trials for numerous cytokine-dependent diseases. 2-Sulfanylimidazole derivatives offer advantages over the prototype inhibitor SB 203580, including fewer cytochrome P450 interactions and better kinetic properties. The aim of this study was to develop novel 1,2,4,5-tetrasubstituted pyridinylimidazoles with acyl residues at the imidazole N1 position that can interact with the kinase's hydrophobic region II (HR II) or sugar pocket (SP) to improve both selectivity and activity. The substitution pattern was optimized by variation of the acyl moiety at the N1 position of the N-aminoimidazole core. Acylation of the amino function was used for optimization and led to potent p38alpha MAPK inhibitors.

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“…[11][12][13][14][15][16][17][18] It is a ubiquitous constituent in medicinal chemistry. Thiazole derivatives exhibit broad antibacterial and antifungal properties, [19][20][21][22][23] i.e.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Transformation of 3-[(4-Arylthiazol-2-yl)(p-tolyl)amino]propanoic Acids, Bis(thiazol-5-yl)phenyl-, Bis(thiazol-5-yl)methane Derivatives, and Their Antimicrobial Activity

Mickevičius¹,

Grybaitė²,

Vaickelionienė³

et al. 2018

HETEROCYCLES

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-Bis(thiazol-5-yl)phenyl-and bis(thiazol-5-yl)methanes were synthesized by the reaction of 2,4-disubstituted thiazoles with aromatic aldehydes or formaldehyde. In addition, modification of the carboxyl group of the molecule was carried out. The reactions afforded compounds bearing various heterocyclic fragments. All the synthesized compounds were tested for their effect on Escherichia coli, Staphylococcus aureus and Mycobacterium luteum bacteria andAspergillus niger and Candida tenuis fungi strains. Some of them exhibited antibacterial activity against test-culture Mycobacterium luteum.

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Syntheses of Aromatic Substituted Hydrazino-thiazole Derivatives to Clarify Structural Characterization and Antioxidant Activity between 3-Arylsydnonyl and Aryl Substituted Hydrazino-thiazoles

Cited by 57 publications

References 26 publications

Mesoionic Sydnone: A Review in Their Chemical and Biological Properties

Mesoionic Sydnone: A Review in Their Chemical and Biological Properties

Synthesis and Biological Testing of N‐Aminoimidazole‐Based p38α MAP Kinase Inhibitors

Synthesis, Transformation of 3-[(4-Arylthiazol-2-yl)(p-tolyl)amino]propanoic Acids, Bis(thiazol-5-yl)phenyl-, Bis(thiazol-5-yl)methane Derivatives, and Their Antimicrobial Activity

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