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![The structures of four antibiotics isolated from Stroptomyces bacteria, Viridomycin A [13], Actinoverdin A, Ferroverdin [9] and Viridomycin E. Viridomycin E has been described in only a single publication [12] and could well exist preferentially as the hexadentate sodium salt, equivalent to the other 3 examples.](publication/337096496/figure/fig1/AS:822779695874049@1573177374942/The-structures-of-four-antibiotics-isolated-from-Stroptomyces-bacteria-Viridomycin-A.png)
The structures of four antibiotics isolated from Stroptomyces bacteria, Viridomycin A [13], Actinoverdin A, Ferroverdin [9] and Viridomycin E. Viridomycin E has been described in only a single publication [12] and could well exist preferentially as the hexadentate sodium salt, equivalent to the other 3 examples.
Source publication
The syntheses of the title compounds demonstrate a privileged introduction of a nitroso (and a hydroxyl via the Baudisch reaction) group to an aromatic ring. These complexes first appeared in the literature as early as 1939, and a range of applications has subsequently been published. However, optimisations of the preparative sequences were not con...
Context in source publication
Context 1
... substituted iron tris(nitrosophenolato) complexes are naturally biosynthesised by particular Streptomycete bacteria as specialised antibiotics [8][9][10][11]. Ferroverdin (Figure 2) was the first confirmed natural product to be isolated [8], although this was rapidly followed by the related Viridomycin A, Actinoviridin and Viridomycin E [12]. These complexes were found to target certain bacteria by disrupting their cell membranes; however, the free ligands were determined to be more effective than the corresponding iron complexes [13]. ...
Citations
... Комплексні сполуки заліза з похідними 2-нафтолу завдяки стійкості до світла за підвищених температур та інтенсивного зеленого забарвлення широко використовуються у виробництві органічних барвників [21]. Останнім часом інтерес до таких сполук значно збільшився завдяки їх застосуванню в елементах оптичних пристроїв як барвників для світлофільтрів, акумуляторів сонячної енергії [21,22]. В цьому випадку практичне значення має натрієва сіль ферату (II) 1-нітрозо-2нафтолу, відома у технології органічних барвників як «пігмент зелений» [21,22]. ...
... Останнім часом інтерес до таких сполук значно збільшився завдяки їх застосуванню в елементах оптичних пристроїв як барвників для світлофільтрів, акумуляторів сонячної енергії [21,22]. В цьому випадку практичне значення має натрієва сіль ферату (II) 1-нітрозо-2нафтолу, відома у технології органічних барвників як «пігмент зелений» [21,22]. Наявність атома заліза як центрального комплексоутворювального йона у поєднанні зі спряженою системою π-електронних зв'язків нафталінових циклів дає підстави очікувати цікавих оптичних і магнітних властивостей цієї сполуки. ...
... Методика експерименту Натрієву сіль комплексу заліза з 1-нітрозо-2-нафтолом синтезували реакцією бісульфітного похідного 1-нітрозо-2-нафтолу та сульфату заліза (ІІ) за наявності NaOH i Na 2 CO 3 згідно з процедурою, описаною в [21][22][23]. ...
Providing macroscopic magnetism in organic materials is a very complex but quite promising scientific problem. The need to create an organic magnet is due to a number of expected advantages, such as lightness, transparency, flexibility, ability to switch under the influence of light (magneto-optics), or chemical influences (sensors), creation of modern toners for digital printing, materials for chemical power sources etc. To understand the mechanism of biological processes, in particular, human thinking and DNA functioning may help to study the state of spin glass, biomagnetism, the mechanism of action of paramagnetic probes in living tissues and others. In the present paper the peculiarities of the structure and magnetic behavior of the iron complex with 1-nitroso-2-naphthol Na[Fe(C10H6(NO2)3] have been studied. The powder X-ray diffraction method determined that the crystal structure of the complex is monoclinic with the space group P2/1. According to cyclic voltammetry, the electrochemical behavior of the complex anion Fe(C10H6(NO2)3] is characteristic of reversible electrochemical systems with one electron transfer. Optical absorption bands are observed in the electronic spectra of the complex at 389, 690, and 763 nm. The dependences of the magnetic susceptibility of the complex on the temperature, frequency and magnetic field strength in the temperature range 1.5–200 K in the external magnetic field up to 90 kE and in the frequency range from 95 to 2000 Hz are obtained and analyzed. At low temperatures, the peculiarities of magnetic behavior characteristic of the state of spin glass are revealed. The EPR spectrum of the complex is a superposition of two lines, the behavior of which is opposite when the temperature changes in the range of 4–293 K, which indicates the unusual dynamics of the molecular surrounding the Fe3+ ion. Such features may be due to the presence of two structurally inhomogeneous magnetic centers that exhibit opposite spin dynamics with changing temperature. The presence of this dynamic can have a significant impact on the properties of the substance.
... Hydroxynitroso compounds are not themselves dyes, because they have potential of developing metal complexes and they might be producing pigments (Raue and Corbett 2000). Green pigment B (1-nitroso-2-naphthol containing iron (II) complex) is utilized for decorating paints on decorator due to its sensitivity to light (Nicholls et al. 2019). The complex of such dyes is generally used for dyeing rubbers and also used in paint and varnish industries. ...
Various types of colored pigments have been recovered naturally from biological sources including shells, flowers, insects, and so on in the past. At present, such natural colored substances (dyes) are replaced by manmade dyes. On the other hand, due to their continuous usage in various purpose, these artificial dyes or colored substances persist in the environmental surroundings. For example, industrial wastewater contains diverse pollutant substances including dyes. Several of these (artificial dyes) were found to be toxic to living organisms. In recent times, microbial-based removal of dye(s) has gained more attention. These methods were relatively inexpensive for eliminating such contaminants in the environmental system. Hence, various researchers were isolated microbes from environmental samples having the capability of decolorizing synthetic dyes from industrial wastewater. Furthermore, the microorganisms which are genetically engineered found higher degradative/decolorize capacity to target compounds in the natural environs. Very few reviews are available on specific dye treatment either by chemical treatments or by bacteria and/or fungal treatments. Here, we have enlightened literature reports on the removal of different dyes in microbes like bacteria (including anaerobic and aerobic), fungi, GEM, and microbial enzymes and also green-synthesized nanoparticles. This up-to-date literature survey will help environmental managements to co-up such contaminates in nature and will help in the decolorization of dyes.
... Ferroverdins, together with the antibiotics viridomycins and actinoverdins, are greenpigmented ferrous (iron(II)) ion (Fe 2+ )-nitrosophenolato complexes [1] produced by a few members of the Streptomyces genus. Ferroverdins A, B, and C were originally isolated from the fermentation broth of Streptomyces WK-5344 [2] and later identified as main compounds produced by the cave-moonmilk-dwelling species Streptomyces lunaelactis [3][4][5][6][7]. ...
Ferroverdins are ferrous iron (Fe2+)-nitrosophenolato complexes produced by a few Streptomyces species as a response to iron overload. Previously, three ferroverdins were identified: ferroverdin A, in which three molecules of p-vinylphenyl-3-nitroso-4-hydroxybenzoate (p-vinylphenyl-3,4-NHBA) are recruited to bind Fe2+, and Ferroverdin B and Ferroverdin C, in which one molecule of p-vinylphenyl-3,4-NHBA is substituted by hydroxy-p-vinylphenyl-3,4-NHBA, and by carboxy-p-vinylphenyl-3,4-NHBA, respectively. These molecules, especially ferroverdin B, are potent inhibitors of the human cholesteryl ester transfer protein (CETP) and therefore candidate hits for the development of drugs that increase the serum concentration of high-density lipoprotein cholesterol, thereby diminishing the risk of atherosclerotic cardiovascular disease. In this work, we used high-resolution mass spectrometry combined with tandem mass spectrometry to identify 43 novel ferroverdins from the cytosol of two Streptomyces lunaelactis species. For 13 of them (designated ferroverdins C2, C3, D, D2, D3, E, F, G, H, CD, DE, DF, and DG), we could elucidate their structure, and for the other 17 new ferroverdins, ambiguity remains for one of the three ligands. p-formylphenyl-3,4-NHBA, p-benzoic acid-3,4-NHBA, 3,4-NHBA, p-phenylpropionate-3,4-NHBA, and p-phenyacetate-3,4-NHBA were identified as new alternative chelators for Fe2+-binding, and two compounds (C3 and D3) are the first reported ferroverdins that do not recruit p-vinylphenyl-3,4-NHBA. Our work thus uncovered putative novel CETP inhibitors or ferroverdins with novel bioactivities.
... Phenazines, whose compound class includes high-valued redox-active structures, such as pyocyanin [87], are self-condensation products of the reaction of benzodithiazoyl radicals. These desirable structures have numerous issues in their supply chains [88][89][90], so alternative syntheses are frequently considered. While the formation of phenazines from radicalised Nand S-containing aromatics was not novel [91], an entirely new method was discovered by Mayer in 1985 when heating the Herz radical generated from 3H-naphtho[2,1d][1,2,3]dithiazole 2-oxide (25a, Scheme 26), forming the target phenazine (25d) in high yield [33]. ...
... Phenazines, whose compound class includes high-valued redox-active structures, such as pyocyanin [87], are self-condensation products of the reaction of benzodithiazoyl radicals. These desirable structures have numerous issues in their supply chains [88][89][90], so alternative syntheses are frequently considered. While the formation of phenazines from radicalised N-and S-containing aromatics was not novel [91], an entirely new method was discovered by Mayer in 1985 when heating the Herz radical generated from 3H-naphtho[2,1-d][1,2,3]dithiazole 2-oxide (25a, Scheme 26), forming the target phenazine (25d) in high yield [33]. ...
The benzo[1,2,3]dithiazole is a unique heteroaromatic functionality whose conjugated profile instils some fascinating electronic properties. This has been historically recognized in the design and manufacture of organic dyes early last century. Although, with the benefit of increased diagnostic techniques and improved understanding, these structures are attracting greater attention in additional research settings, including applications as organic radicals and semiconductors. In addition, the benzodithiazole functionality has been shown to be a valuable synthetic intermediate in the preparation of a variety of other privileged aromatic and heteroaromatic targets, many of which are important APIs. In this review, the authors aim to critically analyse the potential applicability of these compounds to the fields of not only small-scale laboratory synthetic and medicinal chemistry but also commercial-scale processes and increasingly materials chemistry.
... This was observed in both O 2 and air atmospheres. Furthermore, the inactivation or destruction of the αCDCuBr 2 complex could occur due to the formation of complexes between the metal centre and the oxidized amines derivatives [38,39]. These could displace from the metal centre coordination sphere to the bromide ions [40], necessary for the formation of the halogenated intermediate. ...
The α-amination reaction of ketones was studied and the reaction conditions were analysed by green metrics. Propiophenone and two aliphatic ketones, saturated cyclic and acyclic secondary amines were used, carbohydrate Cu²⁺ complexes were the catalysts to obtain the brominate intermediates. Traditional stirring and ultrasound methods were compared. The use of α-CDCuBr2 complex in the presence of propiophenone, morpholine and O2 was the best condition to carry out the α-amination reaction using a One Pot synthesis, with an 80 % yield of product isolated and no by-product was detected.
A simple protocol yielding ortho-substituted nitrosophenols from phenols is demonstrated, in the form of copper(II) bis(nitrosophenolato) complexes. The developed methodology was applied to a range of substrates, confirming the role of the copper in both the formation and protection of the challenging 1, 2-substitution pattern. Using polymer supported thiourea, the Cu could be stripped from the complexes and thus enabled the isolation or identification of the uncoordinated ligands and their decomposition products, in yields generally low in line with the intrinsic high reactivity of 2-nitrosophenols. The product complexes are useful intermediates as demonstrated in revisiting a formal [4 + 2] cycloaddition with dimethylacetylene dicarboxylate to synthesise bicyclic products in variable yields, revealing the product has a novel structure different from those previously reported in the literature.
