Pyridine-derived thiosemicarbazones and their tin(IV) complexes with antifungal activity against Candida spp.

Parrilha, Gabrieli L.; Silva, Jéferson G. Da; Gouveia, Ludmila Ferreira; Gasparoto, Alan K.; Dias, Roberta P.; Rocha, Willian R.; Santos, Danielle Anjos dos; Speziali, Nivaldo L.; Beraldo, Heloísa

doi:10.1016/j.ejmech.2011.01.041

Cited by 70 publications

(33 citation statements)

References 41 publications

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“…Rh(OCET) and Rh(BOCET) have the higher antibacterial effect, although that Rh(NOCET) is a comparable antibacterial effect to them due to Rh(NOCET) have the lower Eg value, i.e. it has higher reactivity than the other two complexes, due to the small difference between the HOMO and LUMO energy values, this is in accordance with the documented values in literature …”

Section: Resultsmentioning

confidence: 99%

Antibacterial, DFT and molecular docking studies of Rh(III) complexes of Coumarinyl‐Thiosemicarbazone nuclei based ligands

Hassan

2017

Applied Organom Chemis

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Coumarinyl thiosemicarbazone derivatives (1E)‐1‐(1‐(2‐oxo‐2H‐chromen‐3‐yl)ethylidene)thiosemicarbazide (OCET), (1E)‐1‐(1‐(6‐bromo‐2‐ oxo‐2H‐chromen‐3‐yl)ethylidene)thiosemicarbazide (BOCET) and 1‐(1‐(3‐oxo‐3H‐benzo[f]chromen‐2‐yl)ethylidene)thiosemicarbazide (NOCET) and their Rh(III) complexes were synthesized, the characterization was carried out by elemental analysis, IR, UV–Visible, mass, magnetic measurement and molar conductance techniques. Data interpretation of the Rh(III) complexes indicates that the ligands of coumarinyl thiosemicarbazone derivatives were formed in stoichiometric ratios as 1:2 (metal: ligand). The studied ligands act as a bidentate ligand by using both azomethine nitrogen and thiol sulphur as monoanion center of donation. The theoretical conformational structure analyses were performed using density functional theory for ligands and complexes at B3LYP functional with 6‐31G(++)d,p basis set for ligands and LANL2DZ basis set for complexes. The charge distribution within the ligands and its Rh(III) complexes was calculated using Mulliken population analysis of (MPA) and natural population analysis (NPA). The antibacterial activity of the prepared compounds was tested against some types of Gram positive and negative bacteria. Molecular docking investigation proved that, the ligands and complexes had interesting interactions with active site amino acids of ribosyltransferase (code: 3GEY).

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Section: Resultsmentioning

confidence: 99%

Antibacterial, DFT and molecular docking studies of Rh(III) complexes of Coumarinyl‐Thiosemicarbazone nuclei based ligands

Hassan

2017

Applied Organom Chemis

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“…SnO 2 nanoparticles exhibit significant industrial applications such as catalyst supports (Jang et al, 2008;Dehbashi et al, 2013;Higuchi et al, 2014;Rabis et al, 2014;Zhao et al, 2014), transparent conducting electrodes (Kleinjan et al, 2008) and gas sensors (Wang et al, 2011;Kim et al, 2012;Xing et al, 2013). Some organotin(IV) compounds are used as PVC stabilizers (Xu et al, 1990), catalysts (Ashfaq et al, 2011;Devendra et al, 2013;Tariq et al, 2013), antioxidants (Jabbar et al, 2012;Sirajuddin et al, 2014), fungicides (Menezes et al, 2005;Singh and Kaushik 2008;Aziz-urRehman et al, 2011;Parrilha et al, 2011;Dias et al, 2012) and as potential antitumor agents (Gleeson et al, 2008;Arjmand et al, 2011;Sun et al, 2011;Verginadis et al, 2011;Khandani et al, 2013;Nath et al, 2013;Carraher and Roner, 2014). These organic-inorganic organotin(IV) complexes may possess a rich diversity of structural motifs.…”

Section: Introductionmentioning

confidence: 97%

Synthesis of novel penta and hexa coordinated monobutyltin(IV) derivatives based on oximes and N-protected amino acids

Srivastava

Maheshwari

Jain

et al. 2015

Main Group Metal Chemistry

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Several new monobutyltin(IV) derivatives containing both oximes and N-protected amino acids have been generated. The compounds having the general formulae BuSn[(L) 2 A], where LH = cyclohexanoneoxime, acetophenoneoxime and AH = C(O)C 6 H 4 C(O)NCHRCOOH (where R = -CH(CH 3 ) 2 , -CH(CH 3 )CH 2 CH 3 , -CH 2 C 6 H 5 ), and BuSn[L(A) 2 ], where LH = cyclohexanoneoxime, acetophenoneoxime and AH = C(O)C 6 H 4 C(O)NCHRCOOH (where R = -CH(CH 3 ) 2 , -CH(CH 3 )CH 2 CH 3 , -CH 2 C 6 H 5 ), were generated by the reactions of monobutyltin(IV) trichloride with sodium salts of oximes and N-protected amino acids in 1:2:1 and 1:1:2 molar ratios in dry boiling benzene. Plausible structures of these compounds were suggested based on physico-chemical and spectroscopic studies. 119 Sn NMR spectroscopic data revealed the presence of five and six coordinated tin centers.

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“…The reaction mixture was kept under reflux for 6 h. After cooling to room temperature the resulting solids were filtered off, washed with ethanol and ether and dried in vacuum. (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) The imidazole-derived hydrazones were prepared by mixing equimolar amounts (2 mmol) of 4(5)-imidazole-carboxaldehyde, 4-(1H-imidazole-1-yl)-benzaldehyde and 4-(1H-imidazole-1-yl)-acetophenone with the desired hydrazide in methanol with addition of three drops of acetic acid as catalyst. The reaction mixture was kept under reflux for 6 h. After cooling to room temperature the resulting solids were filtered off, washed with ethanol and ether and dried in vacuum.…”

Section: Synthesis Of Thiosemicarbazone Derivatives (1-8)mentioning

confidence: 99%

“…Their metal complexes also exhibit antifungal properties [14][15][16]. Hydrazones have previously been reported as active against some species of Candida sp [16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

et al. 2013

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New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehydepara-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-paranitrobenzoyl hydrazone (4(5)ImpNO 2 Ph), 4-(imidazole-1-yl)acetophenone-para-chlorobenzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitrobenzoylhydrazone (4ImAcpNO 2 Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO 2 Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.

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Pyridine-derived thiosemicarbazones and their tin(IV) complexes with antifungal activity against Candida spp.

Cited by 70 publications

References 41 publications

Antibacterial, DFT and molecular docking studies of Rh(III) complexes of Coumarinyl‐Thiosemicarbazone nuclei based ligands

Antibacterial, DFT and molecular docking studies of Rh(III) complexes of Coumarinyl‐Thiosemicarbazone nuclei based ligands

Synthesis of novel penta and hexa coordinated monobutyltin(IV) derivatives based on oximes and N-protected amino acids

Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

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