Abstract:The synthesis of some new thiophenyl-derivatized and furanyl-derivatized phenothiazine and phenoxazine dyestuffs is described. This was achieved by two methods after the synthesis of 6-chloro-5H-benzo[a]phenothiazin-5-one, 6-chloro-5H-benzo[a]phenoxazin-5-one, and 6-chloro-5H-naphtho [2,1-b] pyrido [2,3-e][1,4]oxazin-5-one intermediates via anhydrous base condensation reaction of 2,3-dichloro-1,4-naphthoquinone with 2-aminothiophenol, 2-aminophenol, and 2-aminopyridinol, respectively. The first method involv… Show more
“…Their intense colours and chemical nature make them excellent vat dyes. Besides this, these dyes act as good colourants for paint, ink, papers, candles, soap, and plastic materials [24]. This confirms that the main pigment "1,2-dimethoxy-3H-phenoxazin-3-one" isolated and characterized from the present study may have promising dyeing potential in the textile industry.…”
Filamentous fungi synthesize natural products as an ecological function. In this study, an interesting indigenous fungus producing orange pigment exogenously was investigated in detail as it possesses additional attributes along with colouring properties. An interesting fungus was isolated from a dicot plant, Maytenus rothiana. After a detailed study, the fungal isolate turned out to be a species of Gonatophragmium belonging to the family Acrospermaceae. Based on the morphological, cultural, and sequence-based phylogenetic analysis, the identity of this fungus was confirmed as Gonatophragmium triuniae. Although this fungus grows moderately, it produces good amounts of pigment on an agar medium. The fermented crude extract isolated from G. triuniae has shown antioxidant activity with an IC50 value of 0.99 mg/mL and antibacterial activity against Gram-positive bacteria (with MIC of 3.91 μg/mL against Bacillus subtilis, and 15.6 μg/mL and 31.25 μg/mL for Staphylococcus aureus and Micrococcus luteus, respectively). Dyeing of cotton fabric mordanted with FeSO4 using crude pigment was found to be satisfactory based on visual observation, suggesting its possible use in the textile industry. The orange pigment was purified from the crude extract by preparative HP-TLC. In addition, UV-Vis, FTIR, HRMS and NMR (1H NMR, 13C NMR), COSY, and DEPT analyses revealed the orange pigment to be “1,2-dimethoxy-3H-phenoxazin-3-one” (C14H11NO4, m/z 257). To our understanding, the present study is the first comprehensive report on Gonatophragmium triuniae as a potential pigment producer, reporting “1,2-dimethoxy-3H-phenoxazin-3-one” as the main pigment from the crude hexane extract. Moreover, this is the first study reporting antioxidant, antibacterial, and dyeing potential of crude extract of G. triuniae, suggesting possible potential applications of pigments and other bioactive secondary metabolites of the G. triuniae in textile and pharmaceutical industry.
“…Their intense colours and chemical nature make them excellent vat dyes. Besides this, these dyes act as good colourants for paint, ink, papers, candles, soap, and plastic materials [24]. This confirms that the main pigment "1,2-dimethoxy-3H-phenoxazin-3-one" isolated and characterized from the present study may have promising dyeing potential in the textile industry.…”
Filamentous fungi synthesize natural products as an ecological function. In this study, an interesting indigenous fungus producing orange pigment exogenously was investigated in detail as it possesses additional attributes along with colouring properties. An interesting fungus was isolated from a dicot plant, Maytenus rothiana. After a detailed study, the fungal isolate turned out to be a species of Gonatophragmium belonging to the family Acrospermaceae. Based on the morphological, cultural, and sequence-based phylogenetic analysis, the identity of this fungus was confirmed as Gonatophragmium triuniae. Although this fungus grows moderately, it produces good amounts of pigment on an agar medium. The fermented crude extract isolated from G. triuniae has shown antioxidant activity with an IC50 value of 0.99 mg/mL and antibacterial activity against Gram-positive bacteria (with MIC of 3.91 μg/mL against Bacillus subtilis, and 15.6 μg/mL and 31.25 μg/mL for Staphylococcus aureus and Micrococcus luteus, respectively). Dyeing of cotton fabric mordanted with FeSO4 using crude pigment was found to be satisfactory based on visual observation, suggesting its possible use in the textile industry. The orange pigment was purified from the crude extract by preparative HP-TLC. In addition, UV-Vis, FTIR, HRMS and NMR (1H NMR, 13C NMR), COSY, and DEPT analyses revealed the orange pigment to be “1,2-dimethoxy-3H-phenoxazin-3-one” (C14H11NO4, m/z 257). To our understanding, the present study is the first comprehensive report on Gonatophragmium triuniae as a potential pigment producer, reporting “1,2-dimethoxy-3H-phenoxazin-3-one” as the main pigment from the crude hexane extract. Moreover, this is the first study reporting antioxidant, antibacterial, and dyeing potential of crude extract of G. triuniae, suggesting possible potential applications of pigments and other bioactive secondary metabolites of the G. triuniae in textile and pharmaceutical industry.
“…Stille cross coupling involving compound 33 and tributylthiophenylstannane yielded 6-(thiophen-2-yl)-5 H -benzo[a]phenoxazin-5-one, 38 (Scheme 14 ) [ 50 ]. Scheme 14 Mechanistic representation of synthesis of 6-(thiophen-2-yl)-5 H -benzo[a]phenoxazin-5-one from 6-chloro-5 H -benzo[a]phenoxazin-5-one via Stille coupling [ 50 ] …”
Section: Synthetic Methods To Prepare Several Phenoxazine Derivativesmentioning
Phenoxazines have sparked a lot of interest owing to their numerous applications in material science, organic light-emitting diodes, photoredox catalyst, dye-sensitized solar cells and chemotherapy. Among other things, they have antioxidant, antidiabetic, antimalarial, anti-alzheimer, antiviral, anti-inflammatory and antibiotic properties. Actinomycin D, which contains a phenoxazine moiety, functions both as an antibiotic and anticancer agent. Several research groups have worked on various structural modifications over the years in order to develop new phenoxazines with improved properties. Both phenothiazines and phenoxazines have gained prominence in medicine as pharmacological lead structures from their traditional uses as dyes and pigments. Organoelectronics and material sciences have recently found these compounds and their derivatives to be quite useful. Due to this, organic synthesis has been used in an unprecedented amount of exploratory alteration of the parent structures in an effort to create novel derivatives with enhanced biological and material capabilities. As a result, it is critical to conduct more frequent reviews of the work done in this area. Various stages of the synthetic transformation of phenoxazine scaffolds have been depicted in this article. This article aims to provide a state of the art review for the better understanding of the phenoxazine derivatives highlighting the progress and prospects of the same in medicinal and material applications.
Graphical abstract
“…All the synthesized compounds (5)(6)(7)(8)(9)(10)(11)(12) were screened for their antimicrobial activities at concentration 10 mg/mL in agar media [9]. Using Ciprofloxacin an antibacterial agent and Ketoconazole, an antifungal agent as reference drugs.…”
Palladium catalyzed Suzuki-Miyaura (SM) and Buchwald – Hartwig (BH) cross-coupling reactions of some phenoxazines are reported. The precursor 9,11-diamino-6-chloro-7-oxa-8,10,12-triaza-benzo [a] anthracen-5-one was prepared by anhydrous base mediated reaction of 2,5,6-triamino-pyrimidin-4-ol and 2,3-dichloro-1,4-naphthoquinone in methanol. The molecular structures of the synthesized compounds agreed with UV/visible, FT-IR, 1H-NMR, MS and elemental analysis data. Using Ciprofloxacin and Ketoconazole as reference drugs, the compounds were screened against six (6) micro-organisms, viz: Listeria ivanovii, Staphylococcus aureus, Klebsiellapneumoniae, Escherichia coli, Candida albicans and Aspergillusnigerand were found to show significant activity against L.ivanovii and E. coli bacteria.
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