Spectral study and antifouling assessment of some thiosemicarbazone derivatives

Tadros, Aida B.; El‐Batouti, M.

doi:10.1108/00035590410560958

Cited by 10 publications

(3 citation statements)

References 2 publications

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“…Thiosemicarbazones and thiosemicarbazides are now well established as an important class of sulfur/nitrogen donor ligands, particularly for transition metal ions [ 1 , 2 ], because of the remarkably diverse biological activities observed for these compounds. These activities include antiviral [ 3 , 4 , 5 ], antitumor [ 6 , 7 ], and antimicrobial properties [ 8 ], as well as other industrially important activities, including anticorrosion [ 9 ] and antifouling [ 10 ] effects. Considering all of these properties, it is important to be able to synthesize new series of thiosemicarbazones.…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis of New N1,N4-Substituted Thiosemicarbazones

et al. 2011

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We present an efficient procedure for the synthesis of thirty-six N1,N4-substituted thiosemicarbazones, including twenty-five ones that are reported for the first time, using a microwave-assisted methodology for the reaction of thiosemicarbazide intermediates with aldehydes in the presence of glacial acetic acid in ethanol and under solvent free conditions. Overall reaction times (20–40 min when ethanol as solvent, and 3 min under solvent free conditions) were much shorter than with the traditional procedure (480 min); satisfactory yields and high-purity compounds were obtained. The thiosemicarbazide intermediates were obtained from alkyl or aryl isothiocyanates and hydrazine hydrate or phenyl hydrazine by stirring at room temperature for 60 min or by microwave irradiation for 30 min, with lower yields for the latter. The preliminary in vitro antifungal activity of thiosemicarbazones was evaluated against Aspergillus parasiticus and Candida albicans.

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Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis of New N1,N4-Substituted Thiosemicarbazones

et al. 2011

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“…Some of these derivatives displayed tuberculostatic activity in concentrations >20 mg ml À1 . 10,11 In some cases, the pharmacological activity is conferred by a metallic ion (e.g., iron) associated with the TSC molecule to form a complex. 12 Regardless of the therapeutic potential investigated for over six decades, only a few TSC drug candidates have been approved by the US FDA and implemented in clinics, 13 namely the oral antiseptic ambazone 14 and the antiviral methisazone.…”

Section: Introductionmentioning

confidence: 99%

Self-aggregation behaviour of novel thiosemicarbazone drug candidates with potential antiviral activity

et al. 2010

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The present work aimed to gain further insight into the mechanisms governing the aggregation process of 1-indanone thiosemicarbazone drug candidates. Regardless of the relatively low lipophilicity predicted by theoretical calculations, these compounds were very insoluble in water. This performance was especially notorious for methoxylated (and non-N-allylated) derivatives. Thermal analysis revealed that the introduction of one and two CH 3 O-moieties into the aromatic ring increases the T m pronouncedly from 185 1C to 229 1C and 258 1C, respectively. The formation of nano-aggregates in water was suggested by the appearance of a new strong absorption peak at 233-239 nm in the UV spectra. DLS analysis showed the early formation nanoscopic particles (120-300 nm) that undergo a gradual size growth to generate larger submicron structures; these particles remained invisible to the naked eye. The negatively-charged character of the surface was established by zeta potential measurements. These results suggest the generation of an inner hydrophobic ''core'' due to the interaction of highly hydrophobic aromatic rings that is surface-decorated by CQS groups available in a thiolato anionic form. This aggregation mechanism is supported by the fact that methoxylation of the aromatic ring dramatically strengthens the solute-solute affinity, as expressed by the sharp increase in T m and makes these derivatives much more water-insoluble. Finally, overall findings indicate that for these compounds, solubility predictions based on lipophilicity calculations are not reliable and a more thorough characterization is required.

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“…A heterocyclic analogue has applications in drug development such as bacterial infection, central nervous system disorders, and anti-allergic and analgesic agents. Thiosemicarbazones also exhibit a variety of scientifically promising procedures such as anticorrosion, antifouling, 11 and plant growth-promoting activities 12 and are employed for making electrodes. 13 Thiosemicarbazones can undergo tautomerism and form planar, rigid Schiff bases that are proficient to interact with metal cations that have attracted the attention of researchers to consider thiosemicarbazones as interesting ligands to synthesize metal complexes.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis, Spectroscopic Characterization, and Optical Nonlinearity Response of Novel Salicylaldehyde Thiosemicarbazone Derivatives

et al. 2021

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In this study, seven derivatives of salicylaldehyde thiosemicarbazones (1–7) were synthesized by refluxing substituted thiosemicarbazide and salicylaldehyde in an ethanol solvent. Different spectral techniques (UV–vis, IR, and NMR) were used to analyze the prepared compounds (1–7). Accompanied by the experimental study, quantum chemical studies were also carried out at the M06/6-311G(d,p) level. A comparative analysis of the UV–visible spectra and vibrational frequencies between computational and experimental findings was also performed. These comparative data disclosed that both studies were observed to be in excellent agreement. Furthermore, natural bond orbital investigations revealed that nonbonding transitions were significant for the stability of prepared molecules. In addition, frontier molecular orbital (FMO) findings described that a promising charge transfer phenomenon was found in 1–7. The energies of FMOs were further used to determine global reactivity parameters (GRPs). These GRP factors revealed that all synthesized compounds (1–7) contain a greater hardness value (η = 2.1 eV) and a lower softness value (σ = 0.24 eV), which indicated that these compounds were less reactive and more stable. Nonlinear optical (NLO) evaluation displayed that compound 5 consisted of greater values of linear polarizability ⟨α⟩ and third-order polarizability ⟨γ⟩ of 324.93 and 1.69 × 105 a.u., respectively, while compound 3 exhibited a larger value of second-order polarizability (βtotal) of 508.41 a.u. The NLO behavior of these prepared compounds may be significant for the hi-tech NLO applications.

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Spectral study and antifouling assessment of some thiosemicarbazone derivatives

Cited by 10 publications

References 2 publications

Microwave-Assisted Synthesis of New N1,N4-Substituted Thiosemicarbazones

Microwave-Assisted Synthesis of New N1,N4-Substituted Thiosemicarbazones

Self-aggregation behaviour of novel thiosemicarbazone drug candidates with potential antiviral activity

An Efficient Synthesis, Spectroscopic Characterization, and Optical Nonlinearity Response of Novel Salicylaldehyde Thiosemicarbazone Derivatives

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