75007-33-9Relevant academic research and scientific papers
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 (2014/12/11)
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
Sodium carbonate-mediated facile synthesis of 4-substituted-2-(3,5- dimethylpyrazol-1-yl)thiazoles under solvent-free conditions
Aggarwal, Ranjana,Kumar, Sunil,Singh, Shiv P.
, p. 521 - 525,5 (2020/09/16)
An efficient and facile synthesis of 4-substituted-2-(3,5-dimethylpyrazol- 1-yl)thiazoles 3 was achieved by grinding an equimolar mixture of -haloketones 2 with 3,5-dimethylpyrazol-1-thiocarboxamide 1 in the presence of sodium carbonate under the solvent-
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.
A facile one-pot synthesis of 2-pyrazolyl-4-aryl-thiazoles in a threecomponent reaction
Nalajam, Guravaiah,Vedula, Rajeswar Rao
experimental part, p. 195 - 197 (2009/08/07)
A one-pot multi-component reaction of phenacylbromide, thiosemicarbazide and acetyl acetone or ethyl acetoacetate is described for the preparation of the title compounds. The key features of this methodology are its operational simplicity, mild reaction conditions, and good yields.
β,β-Dibromoketones: A superior alternative to β-bromoketones in hantzsch thiazole synthesis
Prakash, Richa,Kumar, Ajay,Aggarwal, Ranjana,Prakash, Om,Singh
, p. 2501 - 2505 (2008/02/10)
β,β-Dibromoketones (2) have been found to be a superior alternative to the conventionally used β-bromoketones (1) for performing the Hantzsch thiazole synthesis.1 These crystalline, nonlachrymatory compounds are more reactive than 1 as demonstrated by the
Unexpected Formation of α-Thiocyanatoketones in Hantzsch Thiazole Synthesis
Singh, S. P.,Sehgal, Subhash,Singh, Lukhvinder,Dhawan, S. N.
, p. 154 - 155 (2007/10/02)
The reaction of 3,5-dimethylpyrazole-1-thiocarboxamide (3) with α-haloketones (4) yields the corresponding α-thiocyanatoketones (5) or pyrazoles (1) depending upon nature of the halogen.Many such pyrazole derivatives have erroneously been described as thiazolotriazepines in literature.
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).
Synthesis and Mass Spectral Studies of Some 2-(3',5'-Dimethylpyrazol-1'-yl)-4-arylthiazoles and Their 4'-Alkyl/Carboxymethyl Analogues
Singh, S. P.,Kodali, Dharma R.,Dhindsa, G. S.,Sawhney, S. N.
, p. 30 - 33 (2007/10/02)
A number of 2-(3',5'-dimethylpyrazol-1'-yl)-4-arylthiazoles (IIa, d, g, j) and their 4'-alkyl (IIb, c, e, f, h, i, k, l) and 4'-carbethoxymethyl (III) analogues have been synthesized by the condensation of appropriate 2-hydrazino-4-arylthiazoles (I) with pentane-2,4-dione and its 3-substituted analogues.Alkaline hydrolysis of III gives the corresponding acids (IVa-d).The mass spectral studies reveal that the major fragmentation of II involves decomposition of pyrazole ring with the expulsion of methyl cyanide, fission of thiazole ring and the loss of methyl groupfrom the molecular ion.These and the other competing processes which involve skeletal rearrangement in the pyrazole moiety have been supported by the high resolution measurements.Presence of ethoxycarbonyl (III) or a carboxy function (IV), however, triggers an alternative low-energy pathway involving the preferential expulsion of these groups from the molecular ion prior to the decomposition of either of the heterocyclic moieties.The compounds have been screened for their antiinflammatory activity.
