1627-73-2Relevant academic research and scientific papers
Experimental and theoretical study on triazole derivatives as chelating agents to remove Fe++ Ions from wastewater in oil field
Azzam, Eid M. S.,Gad, Elshafie A. M.,Al-Fahemi, Jabir H.
, p. 2586 - 2596 (2020)
In this study, we synthesized triazole derivatives as chelating agents (3-(p-methylphenyl)-5-(phenylsulfonyl)-4H-1,2,4-triazoline (MT), 3-phenyl-5-(phenylsulfonyl)-4H-1,2,4-triazoline (PT), and 3-(p-fluorophenyl)-5-(phenylsulfonyl)-4H-1,2,4-triazoline (FT) to remove Fe++ ions from wastewater in oil field. The effect of synthesized compounds on the removal of iron (II) from iron-contaminated samples (Lab. design) and an industrial wastewater sample studied using DR5000 UV-vis spectrophotometer technique. Removal of iron was studied at different concentrations of FeSO4 solution and field sample concentration. In addition, removal of iron (II) was investigated at different times. The performance of the derivative groups (methyl and fluoro) on chelating of Fe++ ions was studied. The prepared compounds show high efficiency in removing the iron ions from the water samples used. The removal efficiency of the title molecules (MT), (PT), and (FT) was investigated using DMol3 (Materials Studio v7.0) based on quantum descriptors such as EHOMO and ELUMO. Mulliken atomic charges distribution and Fukui indices were estimated to verify the local reactive sites of the molecules. The quantum chemical parameters were found to suitable to interpret the performance of the investigated molecules as a chelating agent for Fe++.
Thiosemicarbazone Complexes of Uranium(IV)
Gr?dler, Dennis,Haseloer, Alexander,Tobeck, Christian,Bulut, Yusuf,Neud?rfl, J?rg M.,Mathur, Sanjay,Ruschewitz, Uwe,Klein, Axel,Wickleder, Mathias S.,Zegke, Markus
, p. 1137 - 1139 (2021)
The first homoleptic thiosemicarbazone complexes of uranium were isolated by reacting uranium tetrachloride in a salt metathesis or acid-base reaction with four equivalents of Na(BzTSC) or H(BzTSC) (BzTSC=benzylthiosemicarbazone), carrying a non-methylated (L1), monomethylated (L2) or dimethylated (L3) terminal amino group, in moderate yields. [U(BzTSCNH2)4] (1), [U(BzTSCNH(CH3))4] (2) and [U(BzTSCN(CH3)2)4] (3) show a remarkable stability towards air, with oxidation potentials in THF between +0.43 and +0.53 V and reduction potentials between ?2.53 and ?2.67 V vs. ferrocene/ferrocenium. The simple methylation of the terminal amino group of the ligand allows for controlled changes in the coordination environments of the complexes. Thermogravimetric analyses indicate that the complexes are stable up to 155 °C.
Thiosemicarbazones as inhibitors of tyrosinase enzyme
Soares, Mariana A.,Almeida, Mariana A.,Marins-Goulart, Carla,Chaves, Otávio A.,Echevarria, Aurea,de Oliveira, Márcia C.C.
, p. 3546 - 3550 (2017)
In the search for compounds which may inhibit the development of melanomas, a series of thiosemicarbazones has been investigated as possible inhibitors of the tyrosinase enzyme. The results showed that all the thiosemicarbazones tested exhibited significant inhibitory effects on the enzyme. Thiosemicarbazones Thio-1, Thio-2, Thio-3 and Thio-4 substituted with oxygenate moieties, were better inhibitors (IC50 0.42, 0.35, 0.36 and 0.44?mM, respectively) than Thio-5, Thio-6, Thio-7 and Thio-8. For the better inhibitors, molecular docking results suggested that the oxygen present in the para position of the aromatic ring is essential for the tyrosinase inhibition, due its high ability for complexation with Cu2+ ions. Inside the active protein pocket, Thio-2 – the best studied inhibitor – is able to interact with the amino acid residues His-155, Gly-170 and Val-172 via hydrogen bonding and hydrophobic force. Thio-2, containing a substituent on the aromatic ring similar to the substrate L-DOPA, showed a competitive inhibition mechanism as viewed in a Lineweaver–Burk plot. The same results were observed in the UV–Vis curves.
Structural, thermal and optical characterization of an organic NLO material - Benzaldehyde thiosemicarbazone monohydrate single crystals
Santhakumari,Ramamurthi
, p. 653 - 659 (2011)
Single crystals of the organic NLO material, benzaldehyde thiosemicarbazone (BTSC) monohydrate, were grown by slow evaporation method. Solubility of BTSC monohydrate was determined in ethanol at different temperatures. The grown crystals were characterized by single crystal X-ray diffraction analysis to determine the cell parameters and by FT-IR technique to study the presence of the functional groups. Thermogravimetric and differential thermal analyses reveal the thermal stability of the crystal. UV-vis-NIR spectrum shows excellent transmission in the region of 200-1100 nm. Theoretical calculations were carried out to determine the linear optical constants such as extinction coefficient and refractive index. Further the optical nonlinearities of BTSC have been investigated by Z-scan technique with He-Ne laser radiation of wavelength 632.8 nm. Mechanical properties of the grown crystal were studied using Vickers microhardness tester. Second harmonic generation efficiency of the powdered BTSC monohydrate was tested using Nd:YAG laser and it is found to be ～5.3 times that of potassium dihydrogen orthophosphate.
Magnetic nanoparticles with chelating shells prepared by RAFT/MADIX polymerization
Markiewicz, Karolina H.,Zembko, Paula,Pó?torak, Katarzyna,Misztalewska, Iwona,Wojtulewski, S?awomir,Majcher, Anna M.,Fornal, Emilia,Wilczewska, Agnieszka Z.
, p. 9223 - 9231 (2016)
In this study, the preparation of multifunctional materials based on magnetic nanoparticles (MNP) and original thiosemicarbazide derivatives is presented. The synthesized nanohybrids consist of an iron oxide core and a polymeric shell, which possesses the ability to complex metal ions. They exhibit superparamagnetic properties and can thus be easily separated from complex mixtures using an external magnetic field (facile separation, purification, and recyclability). Synthesized carbamohydrazonothioate derivatives were polymerized on dithiocarbonate-coated MNPs using the RAFT/MADIX (reversible addition-fragmentation transfer/macromolecular design by interchange of xanthates) method. Three types of nanohybrids were obtained and their physicochemical properties were investigated. The ability of nanohybrids to complex palladium(ii) ions and the spectroscopic properties of the obtained materials were studied. In addition, the hemolytic activity tests of polymer-coated particles were performed in order to confirm their potential in biomedical applications.
Gold(I) complexes with aryl-thiosemicarbazones: Molecular modeling, synthesis, cytotoxicity and TrxR inhibition
Tavares, Tatiane Teixeira,Azevedo, Gustavo Chevitarese,Garcia, Adriana,Carpanez, Arthur G.,Lewer, Pamela Matos,Paschoal, Diego,Müller, Bruno L.,Dos Santos, Hélio F.,Matos, Renato Camargo,Silva, Heveline,Grazul, Richard Michael,Fontes, Ana Paula Soares
, p. 95 - 104 (2017)
Thiosemicarbazones and their metal complexes are of considerable interest because of their chemical and biological properties. Gold(I) compounds form a family of potential anticancer agents that are currently undergoing intense preclinical investigations. Novel gold(I) complexes were obtained through the reaction of aryl-thiosemicarbazone ligands with KAuCl4 and Au(PPh3)Cl. The complexes were characterized by elemental analyses, Raman, IR and NMR spectroscopies, electrospray ionization mass spectrometry, TG/DTA, cyclic voltammetry and with the aid of molecular modeling. The cytotoxicity of the complexes was assessed against tumor cell lines (B16-F10 and CT26.WT) and non-tumor cell line (BHK-21). Most of the tested complexes showed satisfactory cytotoxic activity, some of them being even more cytotoxic in tumor cells than cisplatin with a high selectivity index in the tested cells. The gold complexes with phosphine derivatives showed a better biological response and higher selectivity indices than their respective non-phosphine gold complexes. A preliminary drug-receptor docking study suggests the interaction of thiosemicarbazone ligands with Y116 and E30, which are part of the catalytic N-terminal motif of thioredoxin reductase (TrxR). All compounds were evaluated for their ability to inhibit the activity of the TrxR enzyme. The non-substituted phosphine gold complexes turned out to be effective inhibitors of TrxR when compared to the phosphine analogues. Both complexes, in most of the cases, were more efficient TrxR inhibitors than the free ligands.
Synthesis, crystal structure, spectroscopic, electronic and nonlinear optical properties of potent thiazole based derivatives: Joint experimental and computational insight
Haroon, Muhammad,Khalid, Muhammad,Akhtar, Tashfeen,Tahir, Muhammad Nawaz,Khan, Muhammad Usman,Muhammad, Shabbir,Al-Sehemi, Abdullah G.,Hameed, Shahid
, (2020)
Herein, two new thiazole derivatives: ethyl2-(2-benzylidenehydrazinyl)thiazole-4-carboxylate (3) and ethyl2-(2-(2-hydroxybenzylidene)hydrazinyl)thiazole-4-carboxylate (4) were synthesized by cyclization of 1-benzylidenethiosemicarbazide with ethyl bromopyruvate. The synthesis was validated by spectroscopic techniques like FTIR, 1H- NMR, 13C-NMR and chemical structure of title compounds 3 and 4 has been determined using SC-XRD. Ancillary to experimental analysis, DFT calculations with B3LYP/6-311 + G (d,p) level were performed for comparative analysis of FT-IR spectroscopic data, optimized geometry, frontier molecular orbitals (FMOs), natural bond orbital (NBO) analysis and nonlinear optical (NLO) properties. Overall, experimental findings were supported by corresponding DFT computed results. TDDFT calculations were executed at M06/6-311 + G (d,p) level of theory to calculate the vertical electronic transition states. NBO analysis disclosed that intramolecular charge transfer and hyper-conjugative interactions among bonds provide stability to the investigated compounds 3 and 4. The global reactivity parameters calculated from energy of FMOs indicates that 3 and 4 enclose larger softness and fewer hardness values. NLO results of 3 and 4 were observed better than standard molecule recommended the NLO activity of said compounds. We hope that this joint experimental and computational insight may provide new ways for the utilization of title molecules as NLO material for optoelectronic applications.
Design and synthesis of thiazolylhydrazone derivatives as inhibitors of chitinolytic N-acetyl-β-D-hexosaminidase
Yang, Huibin,Liu, Tian,Qi, Huitang,Huang, Zhisong,Hao, Zesheng,Ying, Junwu,Yang, Qing,Qian, Xuhong
, p. 5420 - 5426 (2018)
N-acetyl-β-D-hexosaminidase (Hex) is potential target for pesticide design. Here, a series of thiazolylhydrazone derivatives were designed, synthesized and evaluated as competitive inhibitors of OfHex1, a Hex from the agricultural pest Ostrinia furnacalis. The derivative 3k, with a (benzyloxy)methyl group at the N3 atom, demonstrated greater potency with a Ki of 10.2 μM. Molecular docking analysis indicated that the (benzyloxy)methyl group of 3k was bound to a previously unexplored pocket formed by Loop478-496. Then further optimization around naphthalene ring led to find the more potency substituent phenyl. The derivative 7, with phenoxyethyl group at R1 and a phenyl group at R2, demonstrated an augmented potency with a Ki of 2.1 μM. Molecular docking analysis indicated that 7 was bound to the active pocket of OfHex1 more favorably than 3k. This work suggests a novel scaffold for developing specific Hex inhibitors.
Combined experimental and theoretical studies on a phenyl thiadiazole-based novel turn-on fluorescent colorimetric Schiff base chemosensor for the selective and sensitive detection of Al3+
Manna, Amit Kumar,Chowdhury, Shubhamoy,Patra, Goutam K.
, p. 10819 - 10832 (2020)
Herein, we have presented a phenyl thiadiazole-based Schiff base receptor, 2-[(Z)-(5-phenyl-1,3,4-thiadiazol-2-ylimino)methyl]-6-methoxy-4-nitrophenol (L) for the first time for turn-on fluorescent, colourimetric detection of Al3+ ions. The chemosensor L displayed very quick responses, excellent selectivity and sensitivity towards Al3+ ions in methanol-Tris-HCl buffer medium (10 mM, pH 7.2, and 1?:?1 v/v) with colourimetric and fluorometric detection limit values of 1.43 × 10-7 M and 1.15 × 10-7 M, respectively. The binding stoichiometry was obtained as 2?:?1 from the Job plot analysis and ESI-MS spectra with the association constant value of 1.76 × 102 M-1/2. The experimental results have further been supported by thorough DFT and TD-DFT studies. The chemosensor L can be applied for the formation of binary logical devices, recovery of contaminated water samples and smartphone-based chemical analysis.
Synthesis and cytotoxicity screening of some synthesized hybrid nitrogen molecules as anticancer agents
El Behery, Mohammed,Mohammed, Faten Z.,Mourad, Ahmed A. E.,Rizzk, Youstina W.,Zaki, Islam
, (2021)
A Series of hybrid organic nitrogen compounds 4, 6, and 8 were synthesized and confirmed through the use of different spectroscopic techniques (IR, NMR, and MS spectrometry) along with elemental analysis. The in vitro antitumor activity of the compounds (4b–d), (6b,c), and (8b,c) against A549 and MCF-7 cell lines and normal breast and lung cells were assessed. Several compounds were found to be potent antitumor agents. Further, in vitro cell cycle study of compounds, 4d and 8c revealed A549 and MCF-7 cell cycle arrest at S and G2/ M phases, respectively; and induce apoptosis at the pre-G1 phase. The apoptosis-inducing activity of synthesized compounds was proofed by the elevation of caspase 3/7 activity and also by up-regulation of the expression of Bax and p53 proteins together with the down-regulation of the expression of the Bcl-2 protein. They also had a strong inhibitory effect against β-tubulin polymerization and topoisomerase IIβ enzyme.
