Aqueous phase synthesis, crystal structure and antimicrobial activity of 4-(substituted phenylazo)-3-methyl-4H-isoxazol-5-one azo dyes

Abstract

3-Methyl-4H-isoxazol-5-one was synthesized at room temperature by simple stirring method from ethyl acetoacetate and hydroxylamine hydrochloride in aqueous medium and coupled with diazotized substituted amine to form series of 4-(substituted phenylazo)-3-methyl-4H-isoxazol-5-ones through green chemistry. All the compounds formed were characterized by IR, 1 H and 13 C NMR spectroscopy, MS and elemental analysis. Crystal structure of novel 4-(4-fluorophenylazo)-3-methyl-4H-isoxazol-5-one was determined by the X-ray diffraction. Antibacterial and antifungal activity was studied against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Staphylococcus pyogenus and Candida albicans, Aspergillus niger, Aspergillus clavatus, respectively. All synthesized compounds were found to be active against a gram-positive bacterium Staphylococcus aureus. Two compounds showed antifungal activity against Candida albicans close to standard greseofulvin.

Crystal structure of 2-(3,5-dimethoxyphenylamino)-3-chloronaphthalene-1,4-dione

“…Synthetic naphthoquinone compounds containing a variety of substituents such as chloro, thio, amino, arylamino are increasingly finding applications in many areas, especially related to textile [1], pharmaceutical [2], agrochemical [3], and drug industries [4]. Dyes are also very important materials [5,6] that most quinones found themselves in [7]. They also display reach biological activities [8] like antifungal [9], antibacterial [10], anticancer [11], antimalarial [12], hypoglycemic [13], analgesic [14], anti-inflammatory [15], and HIV inhibitory [16].…”

Synthesis and pharmacological activities of azo dye derivatives incorporating heterocyclic scaffolds: a review

“…Banpurkar and co-workers reported the synthesis of 3-methyl-4 H -isoxazol-5-one at room temperature by a simple stirring method from ethyl acetoacetate and hydroxylamine hydrochloride in an aqueous medium and coupled it with diazotized substituted amines to form a series of 4-(substituted phenylazo)-3-methyl-4 H -isoxazol-5-ones through green chemistry. 41 The antibacterial activities of the synthesized azo dyes were screened against Escherichia coli , Pseudomonas aeruginosa , Staphylococcus aureus , and Staphylococcus pyogenus . Both 4-(4-fluoro-phenylazo)-3-methyl-4 H -isoxazol-5-one ( 87 ) and 4-(3-acetyl-phenylazo)-3-methyl-4 H -isoxazol-5-one ( 88 ) (Fig.…”

Synthesis, characterization, solvatochromic, and electrochemical investigation of novel 4- methyl coumarin fused azo dyes as an NLO material and their biological studies

“…Recently, researchers have focused on metal-free organic nonlinear optical (NLO) materials considering their diverse applications in data storage, telecommunications, electro-optic (EO) processes, and second-harmonic generation (SHG) photonics [5]. Coumarin azo dyes and their derivatives have been increasingly synthesized because of their significant bioactivities, including antibacterial [6], antifungal [7], antiviral [8], anticonvulsant [9], antidiabetic [10], anti-inflammatory [11], antitubercular [12], anticancer DNA-binding [13],…”