1124-15-8Relevant academic research and scientific papers
Synthesis, characterisation and crystal structure of 3,5-dimethylpyrazole-1-carbothioic acid amide
Chawla, Sukhvinder K.,Kaur, Simrat,Gupta, Nidhi,Hundal, Geeta
, p. 335 - 336 (2007)
3,5-Dimethylpyrazole-1-carbothioic acid amide was obtained (along with acetyl thiosemicarbazide) by the condensation of acetylacetone with thiosemicarbazide and characterised through X-ray diffraction and spectral studies.
Co(ii), Ni(ii) and Cu(ii) complexes with phenylthiazole and thiosemicarbazone-derived ligands: Synthesis, structure and cytotoxic effects
Sobiesiak, Marta,Muziol, Tadeusz,Rozalski, Marek,Krajewska, Urszula,Budzisz, Elzbieta
, p. 5349 - 5361 (2014)
Complexes of Co(ii), Ni(ii) and Cu(ii) with 2-(3,5-dimethyl-1H-pyrazole-1-yl)-4-phenyl-1,3-thiazole (a) and 3,5-dimethyl-1H-pyrazole-1-carbothioamide (b) ligands were synthesized. The crystal and molecular structures of four of them were determined by the X-ray diffraction method. In the complexes with ligand a the metal atom was bound via two nitrogen atoms, whereas ligand b interacted through the nitrogen and sulfur atoms. Comparing the coordination modes observed for both studied ligands, the thiocarbamoyl sulfur atom can participate in metal binding and in bridge formation, whereas the thiazole (aromatic) sulfur atom is not involved in the coordination. This effect seems to enhance (at least partially) conformational flexibility. Hydrogen bonds played a principal role in the crystal network formation of the analyzed compounds. The cytotoxic activity of the complexes against HL-60 and NALM-6 leukemia cells and the WM-115 melanoma cell line was also measured. The copper(ii) complex with the thiosemicarbazone ligand (7b) exhibited relatively high cytotoxicity towards all tested tumor cells. The cytotoxicity of copper(ii) complexes 7b and 9b against the melanoma WM-115 cells was over three times higher than that of cisplatin. This journal is
Palladium(ii) complexes bearing 1-iminothiolate-3,5-dimethylpyrazoles: Synthesis, cytotoxicity, DNA binding and enzymatic inhibition studies
De Moura, Thales Reggiani,Zanetti, Renan Diego,Silva, Debora Eduarda Soares,De Farias, Renan Lira,Mauro, Antonio Eduardo,Pereira, José Clayston Melo,De Souza, Aline Aparecida,Da Silva Siqueira, Fábio,De Souza Júdice, Wagner Alves,Lima, Mauro Almeida,Rocha, Fillipe Vieira,Deflon, Victor Marcelo,De Godoy Netto, Adelino Vieira
, p. 19891 - 19901 (2020)
Four palladium(ii) compounds of general formulae [PdCl(Ln)(PPh3)] {L1 = 3,5-dimethylpyrazole-1-iminothiolate (1); L2 = 3,5-dimethyl-pyrazole-N-methyl-1-iminothiolate (2); L3 = 3,5-dimethylpyrazole-N-ethyl-1-iminothiolate (3); L4 = 3,5-dimethylpyrazole-N-phenyl-1-iminothiolate (4); and PPh3 = triphenylphosphine} have been synthesized. The novel synthesized compounds have been characterized by C, H and N elemental analysis, 1D (1H and 13C) and 2D (HSQC and HMBC) NMR, MS, FT-IR, and molar electrical conductivity measurements. The molecular structure of complex 3 has been solved by single-crystal X-ray crystallography. The stability of the complexes in solution was studied in a DMSO/D2O (7?:?3) solution after 48 h. The antiproliferative activity of all free ligands and the stable palladium complexes 2-4 was assayed using the human breast tumour cell line MCF-7, lung tumour cell line A549 and human fetal lung fibroblast cell line MRC-5. Complex 3 was more active than cisplatin against MCF-7 cells, whilst palladium compounds 2-4 exhibited no drug response towards A549 cells at concentrations 50 μM. The binding properties of compounds 2 and 3 to ct-DNA have been studied using circular dichroism and fluorescence spectroscopy. The topoisomerase IIα inhibition has been studied for complex 2 and 3. The ability of all complexes to inhibit the activity of cathepsin B and L has also been investigated in this work. Compound 4 inhibited more than 50% of the cathepsin B activity at a concentration of 10 μM. Docking simulations have been carried out to gain more information about the interaction of the complexes and cathepsin B.
Synthesis and characterization of chromium(III), molybdenum(II), nickel(II), palladium(II) and platinum(II) complexes, derived from mixed ligands of pyrazole and 2,2-bipyridine
Al-jibouri, Mahmoud Najim,Jabbar, Araf Ismael,Musa, Taghreed M.
, p. 1518 - 1525 (2018)
The recent paper involves the synthesis and characterization studying of chromium(III), Molybdenum(II), nickel(II), palladium(II), and platinum(II) complexes with mixed bidentate ligands namely [3,5-dimethyl-1H-pyrazole-1-carnothioamide and 2,2-Bipyridine] which has been prepared by ring closure of acetylacetone with thiosemicarbazide, in acidified by 2-normality of hydrochloric acid. The new 2-pyrazoline based ligand was identified by mass spectra, NMR and FT-IR spectra. The optimization conditions of pH, time of reaction, and the molar ratio (M:L) were estimated in order to get the pure colored solid complexes chromium(III), molybdenum(II), nickel(II), palladium(II) and platinum(II) by the direct reactions of their metal chlorides in aqueous methanol with the ethanol solution of the ligand. The geometrical structures of the metal complexes were confirmed by measurements of electronic, IR spectra and the detection of magnetic susceptibility and molar conductivity measurements.The octahedral geometry for all complexes was suggested by the results obtained from elemental analyses and other spectral data except that palladium(II) complex which was square-planner in [PdL(bipy)]Cl2 formula.
Synthesis and antibacterial activity of some 4-(coumarin-3-yl)/Aryl 2 (3,5-dimethylpyrazol-1-yl)thiazoles
Aggarwal, Ranjana,Kumar, Sunil,Sharma, Chetan,Aneja, Kamal R.,Singh, Shiv P.
, p. 331 - 336 (2013/09/24)
Reaction of 3-(2-bromoacetyl) coumarins (4) with 3,5-dimethylpyrazol-1- thiocarboxamide (5) results in the formation of title compounds 6. 4-Aryl-2-(3,5-dimethylpyrazol-1-yl) thiazoles (8) which could not be synthesized earlier through this method, were obtained by performing the reaction in presence of a base. All the synthesized compounds have shown moderate to significant antibacterial activity against Gram-positive bacteria namely S. aureus and B. subtilis.
Structural, spectroscopic and computational studies of the HgL 2Cl2 complex (L = 3,5-dimethyl-1-thiocarboxamide pyrazole) and the crystal structure of L
Kovács, Attila,Nemcsok, Dénes,Pokol, Gy?rgy,Szécsényi, Katalin Mészáros,Leovac, Vukadin M.,Ja?imovi?, Zeljko K.,Evans, Ivana Radosavljevi?,Howard, Judith A. K.,Tomi?, Zoran D.,Giester, Gerald
, p. 833 - 840 (2007/10/03)
In the present paper we report the synthesis as well as the structural and vibrational characterisation of the HgL2Cl2 complex (L = 3,5-dimethyl-1-thiocarboxamide). The crystal and molecular structures of both L and the HgL2Cl2 complex were determined by single-crystal X-ray diffraction. The coordination propensity of L to HgCl2 was explored by quantum chemical calculations. We found the preference of the monodentate coordination of L to HgCl2 through the sulfur atom (instead of the "pyridine" nitrogen) to be in agreement with Pearson's acid-base character of the atoms involved and the steric effects. The vibrational properties of HgL2Cl2 were evaluated by a joint FT-IR and quantum chemical analysis. In addition, the thermal decomposition of the complex and ligand is reported. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
Synthesis of some new 2-(pyrazol-1-yl)-4-(pyrimidin-5-yl)thiazoles
Ahluwalia, V. K.,Sharma, Pooja,Goyal, Bindu,Aggarwal, Renu
, p. 920 - 922 (2007/10/03)
The reaction of 1,3-diaryl-5-chloroacetyl-4,6-dioxo-2-thioxohexahydropyrimidines 2a-h with thiosemicarbazide gives 2-hydrazino-4-[1,3-diaryl-4,6-dioxo-2-thioxohexahydropyrimidin-5-yl]thiazoles 3a-h, which on condensation with acetylacetone yield 4-[1,3-di
SYNTHESIS OF PYRAZOLE, 1,3,4-THIADIAZOLE, AND 1,2,4-TRIAZOLE DERIVATIVES BY CONDENSATION OF 1,3-DIOXO COMPOUNDS WITH THIOSEMICARBAZIDE DERIVATIVES
Zelenin, K. N.,Solod, O. V.,Alekseev, V. V.,Pekhk, T. I.,Kuznetsova, O. B.,et al.
, p. 1051 - 1060 (2007/10/02)
The reaction of β-diketones with 2-unsubstituted thiosemicarbazides leads to the formation of the corresponding 1-thiocarbamoyl-5-hydroxy-2-pyrazolines, which readily undergo aromatization to give pyrazoles, while the reaction of benzoylacetaldehyde leads to the formation of the corresponding hydrazone.Acetylacetone 2-methyl- and 2,4-dimethylthiosemicarbazones are inclined to undergo tautomerization and, depending on the conditions, can exist in enehydrazine, hydrazone, 1,2,4-triazoline, and 1,3,4-thiadiazoline forms or mixtures of these forms.Upon heating these substances are converted to mixtures of the 1,3,5-trimethylpyrazole and the corresponding 1,2,4-triazoline-5-thione.The structures of the compounds were studied by means of IR and 1H, 13C, and 15N NMR spectroscopy and mass spectrometry.
Synthesis of 3--2-methylchromones
Garg, C. P.,Sharma, Vinay Prabha,Chhabra, Vinod,Kapoor, R. P.
, p. 469 - 471 (2007/10/02)
A number of 3--2-methylchromones (Va-o) have been synthesized by the condensation of 3-bromoacetyl-2-methylchromones (IVa-d) with 1H-pyrazol-1-thiocarboxamides (IIIa-c).Some of these compounds have been screened for CNS/CVS, antiinflammatory and diuretic activities.
Reported Formation of 3-Arylthiazolotriazepines in the Reaction of 2-Hydrazino-4-arylthiazoles with Pentane-2,4-dione: A Reinvestigation
Singh, S. P.,Diwakar, P.,Sehgal, Subhash,Vaid, R. K.
, p. 1054 - 1055 (2007/10/02)
The condensation of 2-hydrazino-4-arylthiazoles (1a-d) with pentane-2,4-dione (6) results in the formation of 2-(3',5'-dimethylpyrazol-1'-yl)-4-arylthiazoles (2a-d) and not the 3-arylthiazolotriazepines (3) as reported.The correct structural assignment is based on PMR, 13CNMR and high resolution mass spectrometry of the products (2a-d).These products have been obtained by an alternate route involving phenacyl bromides (4) and 3,5-dimethylpyrazol-1-thiocarboxamide (5).
