5351-69-9Relevant articles and documents
Novel, green and sustainable route for synthesis of 5-aryl-4-phenyl-1,2,4-triazolidine-3-thiones
Patil, Mayuri,Mhaldar, Pradeep,Mahadik, Vrushali,Pore, Dattaprasad M.
, (2020)
A highly efficient, one-pot, novel and greener straightforward multi-component approach has been disclosed for the facile synthesis of 5-aryl-4-phenyl-1,2,4-triazolidine-3-thiones from reaction of phenyl isothiocyanate, hydrazine hydrate and diverse aromatic aldehydes/cyclic ketones/isatins in the presence of a novel Lewis acid-surfactant-combined catalyst. High yields, use of ambient temperature and water as a universally accepted green solvent, simple work-up procedure, easy isolation of product, high atom economy makes the present method attractive, sustainable and economical.
Spectral characterization of iron(III) complexes of 2-benzoylpyridine N(4)-substituted thiosemicarbazones
Joseph, Marthakutty,Sreekanth, Anandaram,Suni,Kurup, M. R. Prathapachandra
, p. 637 - 641 (2006)
Three iron(III) complexes (1-3) of 2-benzoylpyridine N(4)-phenyl thiosemicarbazone (HL1) and one iron(III) complex (4) of 2-benzoylpyridine N(4)-cyclohexyl thiosemicarbazone (HL2) were synthesized and characterized by means of different physicochemical techniques viz., molar conductivity measurements, magnetic susceptibility studies and electronic, infrared and EPR spectral studies. The analytical data and the molar conductance measurements of the complexes reveal that two molecules of the ligand and the anion are coordinated to the metal atom in all the four complexes. The magnetic moments of the complexes suggest that they are of low spin. From the infrared spectra of the ligands and the complexes it is confirmed that the ligands coordinate to iron(III) as an anion coordinating via the azomethine nitrogen, pyridyl nitrogen, and the thiolate sulphur. The EPR spectra of the complexes in the polycrystalline state at 298 and 110 K and in DMF solution at 110 K were recorded and all the spectra show three g values indicating that these complexes have rhombic distortion. All the iron(III) complexes in DMF solution at 110 K have similar anisotropic spectra with almost the same gav values, indicating that the bonding in all the complexes is similar and is unaffected by the coordination of the anion.
Structural and spectral perspectives of a novel thiosemicarbazone synthesized from di-2-pyridyl ketone and 4-phenyl-3-thiosemicarbazide
Suni,Prathapachandra Kurup,Nethaji, Munirathinam
, p. 174 - 181 (2006)
A new thiosemicarbazone, HL is synthesized from di-2-pyridyl ketone and 4-phenyl-3-thiosemicarbazide and structurally and spectrochemically characterized. 1H NMR, 13C NMR, COSY, HMQC and IR spectra of the compound are studied and the proton magnetic resonance spectrum reveals some unprecedented observations. The thione form is predominant in the solid state, as supported by the crystal structure and IR data, while a thiol-thione equilibrium is proposed in the solution state by NMR studies. The compound crystallizes into a monoclinic lattice with space group C2/c and the ZE conformation is exhibited by the thiosemicarbazone. Intra- and intermolecular hydrogen-bonding interactions give rise to a two-dimensional packing in the crystal lattice.
1-(2-Methoxybenzylidene)-4-phenylthiosemicarbazide as OFF-ON fluorescent chemodosimeter for detection of Cu2+ in acetonitrile-water binary solvents
Liu, Zhao,Lin, Li-Rong,Huang, Rong-Bin,Zheng, Lan-Sun
, p. 1212 - 1215 (2008)
A novel fluorescent chemodosimeter, 1-(2-methoxybenzylidene)-4-phenylthiolsemicarbazide, was studied. In 90:10 (v/v) mixture of CH3CN and water binary solution, it exhibits high selectivity toward Cu2+ but very low response toward other competitive cations. The Cu2+ promoting cyclization of the thiosemicarbazide to 1,2,4-triazole-3(4H)-thione ring results in observation of the turn-on fluorescence.
Novel tryptanthrin hybrids bearing aminothiazoles as potential EGFR inhibitors: Design, synthesis, biological screening, molecular docking studies, and ADME/T predictions
Banothu, Devendar,Guda, Ramu,Kasula, Mamatha,Korra, Rajashekar,Mekala, Himabindu,Myadaraveni, Prabhakar,Palabindela, Rambabu,Ramesh, Gondru,Ravi, Gangalla
, (2022/04/07)
A variety of novel tryptanthrin aminothiazole analogues 3a-h and 5a-h possessing a biologically active thiazole moiety were synthesized by the reaction of tryptanthrin thiosemicarbazones with different α-bromo-4-substituted-acetophenones compounds. The structures of all the synthesized compounds were characterized by mass, 1H NMR, 13C NMR, and elemental analysis. All the novel synthesized compounds were investigated for their in vitro anticancer activity against three human cancer cell lines (MCF-7, A549, and HeLa) by taking cisplatin as a reference drug. The compounds 3b and 3c displayed excellent anticancer activities against the growth of three human cancer cell lines. EGFR targeting molecular docking investigation revealed that tryptanthrin aminothiazole analogues have better binding energies compared with EGFR inhibitors (Gefitinib, Erlotinib, and Lapatinib). The molecular docking findings back up the experimental anticancer activity results very well. The compounds were also tested for their antibacterial and antioxidant activities. In silico ADMT predictions have been performed that these tryptanthrin aminothiazole analogues have a good pharmacokinetic profile.
Pyridoxal hydrochloride thiosemicarbazones with copper ions inhibit cell division via Topo-I and Topo-IIɑ
Ai, Yu,Chen, Mengyao,Li, Bin,Qi, Jinxu,Zheng, Xinhua,Zheng, Yunyun
, (2022/04/12)
Topoisomerase (Topo) accelerates cell growth and division, and has been a theoretical target for anti-cancer drugs for decades. A series of pyridoxal thiosemicarbazone (PLT) ligands were designed and synthesized, and the dependence of their antiproliferative activity on copper was investigated. The insertion of N-cyclohexyl-2-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)-N-methylhydrazinecarbothioamide hydrochloride (compound 9) and Chlorido(N-cyclohexyl-2-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)-N-methylhydrazinecarbothioamide hydrochloride-O,N,S)?copper(II) nitrate (9-Cu complex) into Topo-I and Topo-II prevented uncoiling of DNA through hydrogen bonds and intermolecular forces. The combination of PLT derivatives and copper gluconate (CuGlu) improved their anti-tumour activity against a cell line with high expression of topoisomerase (SK-BR-3). The non-linear regression equations of the inhibitory activity and anti-tumour activity of Topo-I and Topo-IIɑ in SK-BR-3 cells had R2 values of 0.93 and 0.94, respectively. In addition to lipophilicity, inhibition of topoisomerase also affected the activity of PLT ligands by coordinating with copper ions. At the cellular level, PLTs and CuGlu penetrate the cell membrane to form metabolites in the cell, thus selectively inhibiting the activity of Topo-I and Topo-IIɑ, and ultimately inhibiting cell division. These findings will inform the design of future anti-cancer thiosemicarbazone drugs.
Cloud point extraction procedure for preconcentration of Co2+, Ni2+and Cu2+from water and biological samples using a thiosemicarbazone derivative as a complexing agent
Erfan, Eman A.,Mortada, Wael I.,El-Asmy, Hala A.,El-Defrawy, Mohamed M.
, p. 3431 - 3437 (2021/06/22)
An accurate and simple preconcentration procedure was presented for cloud point extraction of Co2+, Ni2+ and Cu2+ from water, blood and urine samples. The procedure based on complexation of the metal ions with (E)-2-(2,4-dihydroxybenzylidene)-Nphenylhydrazine- 1-carbothioamide (DHBPHC) and subsequent extraction into a surfactant-rich phase of Triton X-114. The optimized procedure (50 mL solution; pH 6; 1 × 10-4 mol L-1 of DHBPHC; 0.08% (v/v) Triton X-114) exhibits linear range up to 500 μg L-1 and limit of detection of 0.34, 0.94 and 0.83 μg L-1 for Co2+, Ni2+ and Cu2+, respectively. Most potentially interferants did not impact the extraction process. The procedure was applied for preconcentration and determination of Co2+, Ni2+ and Cu2+ in water, blood and urine by flame atomic absorption spectrometry.
Design, Synthesis, Biological Evaluation, and Computational Studies of Novel Fluorinated Candidates as PI3K Inhibitors: Targeting Fluorophilic Binding Sites
Tantawy, Ahmed H.,El-Behairy, Mohammed Farrag,Abd-Allah, Walaa Hamada,Jiang, Hong,Wang, Man-Qun,Marzouk, Adel A.
, p. 17468 - 17485 (2021/12/02)
Highly fluorinated candidates containing anticancer pharmacophores like thiosemicarbazone (5a-e) and its cyclic analogues hydrazineylidenethiazolidine (6a-e), 2-aminothiadiazole (7a-e), and 2-hydrazineylidenethiazolidin-4-one (8a-e) were synthesized, and their cytotoxic activity was assayed against 60 tumor cell lines. Compounds 6c, 7b, and 8b displayed the most potent activity with lower toxic effects on MCF-10a. In vitro phosphatidylinositol 3-kinase (PI3K) enzyme inhibition was performed. Compound 6c displayed half-maximal inhibitory concentration (IC50, μM) values of 5.8, 2.3, and 7.9; compound 7b displayed IC50 values of 19.4, 30.7, and 73.7; and compound 8b displayed IC50 values of 77.5, 53.5, and 121.3 for PI3Kα, β, and δ, respectively. Moreover, cell cycle progression caused cell cycle arrest at the S phase for compounds 6c and 8b and at G1/S for compound 7b, while apoptosis was induced. In silico studies; molecular docking; physicochemical parameters; and absorption, distribution, metabolism, excretion, and toxicity (ADMET) analysis were performed. The results showed that compound 6c is the most potent one with a selectivity index (SI) of 39 and is considered as a latent lead for further optimization of anticancer agents.
Diaryl-substituted thiosemicarbazone: A potent scaffold for the development of New Delhi metallo-β-lactamase-1 inhibitors
Li, Jia-Qi,Sun, Le-Yun,Jiang, Zhihui,Chen, Cheng,Gao, Han,Chigan, Jia-Zhu,Ding, Huan-Huan,Yang, Ke-Wu
, (2020/12/30)
The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has become an emerging public health threat. Inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. A potent scaffold, diaryl-substituted thiosemicarbazone, was constructed and assayed with metallo-β-lactamases (MβLs). The obtained twenty-six molecules specifically inhibited NDM-1 with IC50 0.038–34.7 μM range (except 1e, 2e, and 3d), and 1c is the most potent inhibitor (IC50 = 0.038 μM). The structure-activity relationship of synthetic thiosemicarbazones revealed that the diaryl-substitutes, specifically 2-pyridine and 2-hydroxylbenzene improved inhibitory activities of the inhibitors. The thiosemicarbazones exhibited synergistic antimycobacterial actions against E. coli-NDM-1, resulted a 2–512-fold reduction in MIC of meropenem, while 1c restored 16–256-, 16-, and 2-fold activity of the antibiotic on clinical isolates ECs, K. pneumonia and P. aeruginosa harboring NDM-1, respectively. Also, mice experiments showed that 1c had a synergistic antibacterial ability with meropenem, reduced the bacterial load clinical isolate EC08 in the spleen and liver. This work provided a highly promising scaffold for the development of NDM-1 inhibitors.
Design, synthesis and biological evaluation of novel 5-(4-chlorophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiols as an anticancer agent
Patel, Krupa R.,Brahmbhatt, Jpan G.,Pandya, Pranav A.,Daraji, Drashti G.,Patel, Hitesh D.,Rawal, Rakesh M.,Baran, Sujit K.
, (2021/02/12)
Cellular tumor antigen p53 is significant for cancer prevention and its mutation is most documented genomic change in human cancers. Thus, restoration of p53 function by interruption of the p53-MDM2 interaction opens up a prospect for a nongenotoxic anticancer therapeutic strategy. A novel series of molecules comprising 1,2,4-triazole-3-thiol scaffold were successfully discovered by structure-based designing approach. In silico modules predicted that 5-(4-chlorophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiol derivatives have draggability and ability to mimic critical binding residues of p53. All target compounds were assayed for their in vitro antiproliferative activity against A549, U87 and HL60 cell lines. Twelve out of sixteen compounds exhibited good in vitro inhibitory activity in micromolar range. Especially, compound 6h possessed acute antitumor activity with IC50 values 3.854, 4.151 and 17.522 μM against three tested cell lines. It represents as a promising lead for further optimization and a template for development of novel antitumor agents.
