Synthesis of heterocyclic metal complexes and their evaluation as marine antifoulants

Osman, Maher M.; El‐Malek, M.M. Abd; Tadros, Aida B.; Michael, Atef M.

doi:10.1002/jctb.280620107

Cited by 9 publications

(4 citation statements)

References 2 publications

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“…Although the main source of Cu contamination in cultured fish from RC remains unclear, the contamination in fish from FF was due to a CuSO 4 treatment that occurred 3 weeks before the June sampling and was intended to treat an ectoparasitic infection of Amydodinium ocellatum (Fernandes et al 2007). High levels of Cu and Zn have been reported in water and sediments from harbors and marinas (Osman et al 1995;Schiff et al 2004). Thus, increasing anthropogenic use of these essential trace metals may certainly contribute to an increase in its environmental concentrations.…”

Section: Metal Exposure and Metallothioneinsmentioning

confidence: 98%

Assessing pollutant exposure in cultured and wild sea bass (Dicentrarchus labrax) from the Iberian Peninsula

2009

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The aquaculture industry is an expanding activity, mainly due to the world population demand of fish. However, intensive production and the use of chemicals have raised environmental concerns and have questioned the quality of cultured fish in comparison to wild fish. Up to date, there is little information regarding pollutant residues in cultured stocks and the risks associated to consumption. Here we summarize recent data on pollutants exposure, together with biochemical responses in both cultured and wild sea bass (Dicentrarchus labrax) from the Iberian Peninsula. The obtained data highlights the use of chemicals in current aquaculture practices as a significant source of pollution in cultured fish that poses a risk to exposed individuals and may negatively impact aquatic ecosystems. Nonetheless, a controlled use of those chemicals and a careful selection of the aquaculture location can ensure relatively low and homogeneous levels of pollutants in cultured fish in comparison to wild specimens.

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Section: Metal Exposure and Metallothioneinsmentioning

confidence: 98%

Assessing pollutant exposure in cultured and wild sea bass (Dicentrarchus labrax) from the Iberian Peninsula

2009

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“…1,3,4‐Thiadiazoles were also used as lubricants, dyes, corrosion and oxidation inhibitors, liquid crystals and optoelectronic materials . Moreover, their herbicidal, insecticidal, fungicidal and algicidal properties have been investigated. Besides the information on the wide range of thiadiazoles applications and extensive studies on their chemistry, no systematic studies on their NMR properties have been published.…”

Section: Introductionmentioning

confidence: 99%

Multinuclear magnetic resonance studies of 2‐aryl‐1,3,4‐thiadiazoles

Gierczyk

Cegłowski

Kaźmierczak

et al. 2012

Magnetic Reson in Chemistry

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“…3 While 1,3,4-thiadizoles have received attention as a sulfur donor subunit, 4 very little is known about the corporation of heterocylic compounds into macrocyclic compounds. 1a,5 As part of our systematic efforts1 6 aimed at the synthesis of new macrocyclic ligands fused with 1,3,4-thiadiazoles, we reported 6e our attempt to synthesize novel macrocycles that incorporate 2-imino-5-mercapto-3H-1,3,4-thiadiazolines.…”

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confidence: 99%

“…6e,8 In addition to this evidence, a strong imido band at 1603 cm -1 was seen in the IR spectrum, representing a shift to a shorter wavenumber than that of the amide (1661 cm showing the atom numbering scheme with 30% probability ellipsoids. The C2-axis passes through atoms O1 and O2: S1-C3 1.742(5); S2-C3 1.744(5); S2-C6 1.756(5); N1-C3 1.288(6); N1-N2 1.377(6); N2-C4 1.465(6); N2-C6 1.339(6); N3-C6 1.304(6); O3-C7 1.231(6); N3-C7 1.378(6); C3-S2-C6 87.6(2); C3-N1-N2 109.9(4); N1-N2-C6 118.1(4); N2-C6-S2 108.8 (4). structure of macrocycle 4b, determined by X-ray diffraction, is shown in Figure 1.…”

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confidence: 99%

Synthesis and Crystal Structures of Macrocycles Containing 2-Imino-5-mercapto-3H-1,3,4-thiadiazolines

Cho¹,

Hwang²,

Suh³

et al. 2010

Bulletin of the Korean Chemical Society

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-5-mercapto-3H-1,3,4-thiadiazoline † This paper is dedicated to the memory of Prof. Chi-Sun Hahn.The design and synthesis of new class of macrocycles with novel shapes and heterocyclic moiety continue to be the topics of current interest, 1 because they can act as a ligand in asymmetric catalysis 2 and as a host molecule for the incorporation of guest molecule or ions.3 While 1,3,4-thiadizoles have received attention as a sulfur donor subunit, 4 very little is known about the corporation of heterocylic compounds into macrocyclic compounds.1a,5 As part of our systematic efforts1 6 aimed at the synthesis of new macrocyclic ligands fused with 1,3,4-thiadiazoles, we reported 6e our attempt to synthesize novel macrocycles that incorporate 2-imino-5-mercapto-3H-1,3,4-thiadiazolines. Imino group and mercapto group of 2-imino-5-mercapto-3H-1,3,4-thiadiazoline might show novel role when the molecule works as a host for the corporation of a guest molecule.As part of the ongoing study of heterocycles containing 2-imino-5-mercapto-3H-1,3,4-thiadiazolines, we report here the synthesis of macrocycles (4a, 4b, 4c, 4d, 4e, and 4f) containing two 2-imino-5-mercapto-3H-1,3,4-thiadizoline subunits linked at the 3-and 5-positions of the heterocyclic unit. The macrocycles were prepared from 1, as shown in Scheme 1. The spacers between 5 and 5' are CH2CH2, (CH2CH2)2O, and m-xylene, respectively, and the 3-3' spacer is (CH 2 CH 2 ) 2 Compound (1) was regiospecifically S-alkylated under basic conditions, to give 5-amino-2-alkylthio-1,3,4-thiadiazole (2). 6e,7 In addition, 5-substituted 2-acylamino-1,3,4-thiadiazoles (3) were also regiospecifically alkylated at the N(3) position under basic conditions to yield a single 3-alkylated endo-product. 6e,8 These reactions were used for macrocycle ring formation.Compound 2 was synthesized from 1 according the above procedure with an appropriate α,ω-dibromoalkane in the presence of KOH in ethanol to yield the S-alkylated dimer (2). Benzolylation of the amino group of 2 (7.2 -7.3 ppm) was performed to create 3. As evidenced by spectroscopic data, this reaction regiospecifically alkyalted the N(3) position of 3 at the NH 2 (endo-product), as has been observed in the benzoylation of 2-amino-5-alkylthio-1,3,4-thiadiazoles. 6e,8 In 3b, the NH2 signals characteristic of compound 2b were replaced by typical NHCOPh signals appearing at 13.12 and at 8. 12-7.54, 165.2, 133.0, 131.2, 128.6, and at 128.3 ppm in the 1 H and 13 C NMR spectra, respectively. In the 13 C NMR spectrum, the chemical shifts of C(2) and C(5) in the 1,3,4-thiadiazole of 2b (150.0 and 169.5 ppm) changed to those of 3b (159.5 and 159.0 ppm), as observed for 2-amino-5-alkylthio-1,3,4-thiadizole and 2-benzoylamino-5-alkylthio-1,3,4-thiadiazole. Furthermore, a characteristic carbonyl band was observed in the IR spectrum at 1661 cm -1 and in the 13 C NMR spectrum at 165.2 ppm. As expected, the cyclization reaction, which was facilitated by N,Nbisalkylation between the benzolylated compound (3) and the appropriate α,ω-dibromoalkan...

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Synthesis of heterocyclic metal complexes and their evaluation as marine antifoulants

Cited by 9 publications

References 2 publications

Assessing pollutant exposure in cultured and wild sea bass (Dicentrarchus labrax) from the Iberian Peninsula

Assessing pollutant exposure in cultured and wild sea bass (Dicentrarchus labrax) from the Iberian Peninsula

Multinuclear magnetic resonance studies of 2‐aryl‐1,3,4‐thiadiazoles

Synthesis and Crystal Structures of Macrocycles Containing 2-Imino-5-mercapto-3H-1,3,4-thiadiazolines

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