2-Acetylpyridine- and 2-benzoylpyridine-derived thiosemicarbazones and their antimony(III) complexes exhibit high anti-trypanosomal activity

Parrilha, Gabrieli L.; Dias, Roberta P.; Rocha, Willian R.; Mendes, Isolda C.; Benítez, Diego; Varela, Javier; Cerecetto, Hugo; González, Mercedes; Melo, Cristiane Moutinho Lagos de; Neves, Juliana K.A.L.; Pereira, Valéria Rêgo Alves; Beraldo, Heloísa

doi:10.1016/j.poly.2011.10.018

Cited by 36 publications

(13 citation statements)

References 43 publications

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“…29 Similar medium-long Sb–N distances (2.240 and 2.358 Å) were found for dichloro[ N (4)- o -fluorophenyl2-acetylpyridinethiosemicarbazonato]antimony(III). 30 While the Sb–N distance of 2.029 Å is treated as a covalent bond in [(η 1 -Me 2 SiNDipp)NHDippSbCl 2 ] (Dipp = 2,6-diisopropylphenyl), the authors proposed no bonding interaction for the Sb–N separation at 2.66 Å. 31 This short literature survey does not answer the key question of whether the Co3-centered complex is covalently bonded to the cluster anion via a Sb–N bond.…”

Section: Resultsmentioning

confidence: 99%

Covalent Co–O–V and Sb–N Bonds Enable Polyoxovanadate Charge Control

et al. 2017

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The formation of [{CoII(teta)2}{CoII2(tren)(teta)2}VIV15SbIII6O42(H2O)]·ca.9H2O [teta = triethylenetetraamine; tren = tris(2-aminoethyl)amine] illustrates a strategy toward reducing the molecular charge of polyoxovanadates, a key challenge in their use as components in single-molecule electronics. Here, a V–O–Co bond to a binuclear Co2+-centered complex and a Sb–N bond to the terminal N atom of a teta ligand of a mononuclear Co2+ complex allow for full charge compensation of the archetypal molecular magnet [V15Sb6O42(H2O)]6–. Density functional theory based electron localization function analysis demonstrates that the Sb–N bond has an electron density similar to that of a Sb–O bond. Magnetic exchange coupling between the VIV and CoII spin centers mediated via the Sb–N bridge is comparably weakly antiferromagnetic.

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Section: Resultsmentioning

confidence: 99%

Covalent Co–O–V and Sb–N Bonds Enable Polyoxovanadate Charge Control

et al. 2017

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“…One of the arguments for the study of 4-thiazolidine-based compounds as antitrypanosomal agents is the thesis that thiazoles, especially 4-thiazolidinones, are considered as thioureas/thiosemicarbazones' cyclic analogues and biomimetics [42,96,108,109]. Different (thio)ureas/(thio)semicarbazides were reported as inhibitors of the trypanosome proliferation [110][111][112] and had shown high affinity to the antitrypanosomal targets: cruzain and rhodesain [109,113], cysteine proteases [114], etc. Different classes of "drug-like" molecules based on a thiazolidinone scaffold have been designed and synthesized in the process of search for antitrypanosomals [42,[115][116][117][118][119].…”

Section: -Thiazolidinone Frame In the Design Of Antitrypanosomalsmentioning

confidence: 99%

Thiazolidinone-Related Heterocyclic Compounds as Potential Antitrypanosomal Agents

Kryshchyshyn¹,

Kaminskyy²,

Grellier³

et al. 2021

Azoles - Synthesis, Properties, Applications and Perspectives

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Human African trypanosomiasis (HAT) and Chagas disease are neglected tropical diseases (NTDs) due to parasite protists from the Trypanosoma genus transmitted by insect vectors. Trypanosomiases affect mostly poor populations in the developing countries, and the development of new antitrypanosomal drugs is underinvested by governments and the pharmaceutical industry. In this chapter, we described the development of 4-thiazolidinone and thiazole derivatives with heterocyclic fragments which exhibit good inhibition of trypanosome growth and might constitute potential candidates for the development of new drugs against trypanosomiasis. Antitrypanosomal design, mainly within structure-based design, led to the synthesis of 5-ene-4-thiazolidinone-3-alkanecarboxylic acids; 2,3-disubstituted 4-thiazolidinones; thiazolidinone-pyrazoline, phenylindole-thiazolidinone, and imidazothiadiazole-thiazolidinone hybrids; as well as 4-thiazolidinone-based fused heterocycles, especially thiopyrano[2,3-d]thiazoles, and non-thiazolidinone compounds-namely, isothiocoumarine derivatives. Moreover, antitrypanosomal 4-thiazolidinones are of special interest in the search for new antimalarial and antileishmanial agents. Also many active anticancer agents among the abovementioned 4-thiazolidinones have been discovered.

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“…Thiosemicarbazones are basically Schiff bases obtained by the condensation of a thiosemicarbazide, prepared from an aryl, aralkyl, or alkyl isothiocyanate and hydrazine, with an aldehyde or ketone under ambient conditions (Klayman et al 1979 ; Padhye and Kauffman 1985 ; Beraldo et al 2000 , 2001 ; Mendes et al 2001 ; Lobana et al 2009 ; Soares et al 2012 ; Cobeljic et al 2014 ). Thiosemicarbazone derivatives are of considerable interest due to their versatility as ligands bearing suitable donor atoms for coordination to metals with strong coordinating ability toward different metal ions (Parrilha et al 2011 , 2012 ; Singh and Singh 2015 ). They show a wide range of chemical properties depending on the parent aldehyde or ketone; in particular, if these are heterocyclic aromatic systems, their nature seems to enhance their activity (Kovala-Demertzi et al 2005 ; Prathima et al 2010 ).…”

Section: Introductionmentioning

confidence: 99%

Spectrophotometric determination of Cu(II) in soil and vegetable samples collected from Abraha Atsbeha, Tigray, Ethiopia using heterocyclic thiosemicarbazone

2016

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Two selective and sensitive reagents, 2-acetylpyridine thiosemicarbazone (2-APT) and 3-acetylpyridine thiosemicarbazone (3-APT) were used for the spectrophotometric determination of Cu(II). Both reagents gave yellowish Cu(II) complex at a pH range of 8.0–10.0. Beer’s law was obeyed for Cu(II)–2-APT and Cu(II)–3-APT in the concentration range of 0.16–1.3 and 0.44–1.05 µg/mL, respectively. The molar absorptivity and of Cu(II)–2-APT and Cu(II)–3-APT were 2.14 × 104 at 370 nm, and 6.7 × 103 L/mol cm at 350 nm, respectively, while the Sandell’s sensitivity were 0.009 and 0.029 µg/cm2 in that order. The correlation coefficient of the standard curves of Cu(II)–2-APT and Cu(II)–3-APT were 0.999 and 0.998, respectively. The detection limit of the Cu(II)–2-APT and Cu(II)–3-APT methods were 0.053 and 0.147 µg/mL, respectively. The results demonstrated that the procedure is precise (relative standard deviation <2 %, n = 10). The method was tested for Cu(II) determination in soil and vegetable samples. Comparisons of the results with those obtained using a flame atomic absorption spectrophotometer for Cu(II) determination also tested the validity of the method using paired sample t test at the 0.05 level showing a good agreement between them.

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2-Acetylpyridine- and 2-benzoylpyridine-derived thiosemicarbazones and their antimony(III) complexes exhibit high anti-trypanosomal activity

Cited by 36 publications

References 43 publications

Covalent Co–O–V and Sb–N Bonds Enable Polyoxovanadate Charge Control

Covalent Co–O–V and Sb–N Bonds Enable Polyoxovanadate Charge Control

Thiazolidinone-Related Heterocyclic Compounds as Potential Antitrypanosomal Agents

Spectrophotometric determination of Cu(II) in soil and vegetable samples collected from Abraha Atsbeha, Tigray, Ethiopia using heterocyclic thiosemicarbazone

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