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.
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.
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.
Insight on a new indolinone derivative as an orally bioavailable lead compound against renal cell carcinoma
Fouad, Marwa A.,Lotfy, Raghda A.,Mahmoud, Walaa R.,Zaki, Mayssoune Y.
, (2021/06/15)
A series of novel 3-indolinone-thiazolidinones and oxazolidinones 4a-k was synthesized via molecular hybridization approach and sequentially evaluated to explore its cytotoxic activity. The cytotoxicity screening pointed toward the N-cyclohexyl thiazolidinone derivative 4f that revealed promising renal cytotoxicity against CAKI-1 and UO-31 renal cancer cell lines with IC50 values 4.74 and 3.99 μM, respectively, which were comparable to those of sunitinib along with good safety threshold against normal renal cells. Further emphasis on compound 4f renal cytotoxicity was achieved via different enzyme assays and CAKI-1 and UO-31 cell cycle analysis. The results were supported by in silico studies to explore its physicochemical, pharmacokinetic and drug-likeness properties. Finally, compound 4f was subjected to an in vivo pharmacokinetic study through two different routes of administration showing excellent oral bioavailability. This research represents compound 4f as a promising candidate against renal cell carcinoma.
Preparation and application of thiosemicarbazone compound
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Paragraph 0010; 0014; 0015, (2021/02/20)
The invention discloses a thiosemicarbazone compound, and biological activity analysis is carried out on the thiosemicarbazone compound. The invention also discloses application of the thiosemicarbazone compound in preparation of antibacterial drugs. According to the invention, important intermediates 6a-6h are synthesized from hydrazine hydrate and react with adamantane benzaldehyde respectivelyto synthesize eight adamantane aromatic aldehyde thiosemicarbazone compounds, the structures of the compounds can be confirmed by infrared, nuclear magnetic hydrogen spectrum, carbon spectrum and massspectrum methods, and the antibacterial activity of the compounds is tested in vitro. The result shows that the compound has a good antibacterial effect on escherichia coli and bacillus subtilis.
Carbazole-based semicarbazones and hydrazones as multifunctional anti-Alzheimer agents
Chaudhary, Bharat N.,Gandhi, Bhumi,Kanhed, Ashish M.,Patel, Dushyant V.,Patel, Kirti V.,Patel, Kishan B.,Patel, Nirav R.,Prajapati, Navnit K.,Shah, Bhavik S.,Teli, Divya M.,Yadav, Mange Ram
, (2021/07/14)
With the aim to combat a multi-faceted neurodegenerative Alzheimer’s disease (AD), a series of carbazole-based semicarbazide and hydrazide derivatives were designed, synthesized and assessed for their cholinesterase (ChE) inhibitory, antioxidant and biometal chelating activity. Among them, (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(pyridin-2-yl)hydrazinecarbothioamide (62) and (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(5-chloropyridin-2-yl)hydrazinecarbothioamide (63) emerged as the premier candidates with good ChE inhibitory activities (IC50 values of 1.37 μM and 1.18 μM for hAChE, IC50 values of 2.69 μM and 3.31 μM for EqBuChE, respectively). All the test compounds displayed excellent antioxidant activity (reduction percentage of DPPH values for compounds (62) and (63) were 85.67% and 84.49%, respectively at 100 μM concentration). Compounds (62) and (63) conferred specific copper ion chelating property in metal chelation study. Molecular docking studies of compounds (62) and (63) indicate strong interactions within the active sites of both the ChE enzymes. Besides that, these compounds also exhibited significant in silico drug-like pharmacokinetic properties. Thus, taken together, they can serve as a starting point in the designing of multifunctional ligands in pursuit of potential anti-AD agents that might further prevent the progression of ADs. Communicated by Ramaswamy H. Sarma.
Synthesis and antibacterial activity of novel Schiff bases of thiosemicarbazone derivatives with adamantane moiety
Zhu, Jiahui,Teng, Guosheng,Li, Dongfeng,Hou, Ruibin,Xia, Yan
, p. 1534 - 1540 (2021/06/16)
Increased bacterial resistance to antibiotics is a major threat to human health, and it is particularly important to develop novel antibiotic drugs. Here, we designed a series of Schiff base thiosemicarbazone derivatives containing an adamantane moiety, and carried out the structural characterization of the compounds and in vitro antibacterial activity tests. Compound 7e was as effective as the commonly used antibiotic ampicillin against the Gram-negative bacterium Escherichia coli, and compound 7g had a good inhibitory effect against Gram-positive Bacillus subtilis. These findings provide data for the development of better thiosemicarbazone antibacterial agents.
