103-85-5Relevant articles and documents
Dixon, A. E.
, p. 541 - 552 (1901)
Effect of N-1 arylation of monastrol on kinesin Eg5 inhibition in glioma cell lines
Gon?alves, Itamar Luís,Rockenbach, Liliana,Das Neves, Gustavo Machado,G?ethel, Gabriela,Nascimento, Fabiana,Porto Kagami, Luciano,Figueiró, Fabrício,Oliveira De Azambuja, Gabriel,De Fraga Dias, Amanda,Amaro, Andressa,De Souza, Lauro Mera,Da Rocha Pitta, Ivan,Avila, Daiana Silva,Kawano, Daniel Fábio,Garcia, Solange Cristina,Battastini, Ana Maria Oliveira,Eifler-Lima, Vera Lucia
, p. 995 - 1010 (2018)
An original and focused library of two sets of dihydropyrimidin-2-thiones (DHPMs) substituted with N-1 aryl groups derived from monastrol was designed and synthesized in order to discover a more effective Eg5 ligand than the template. Based on molecular docking studies, four ligands were selected to perform pharmacological investigations against two glioma cell lines. The results led to the discovery of two original compounds, called 20h and 20e, with an anti-proliferative effects, achieving IC50 values of about half that of the IC50 of monastrol in both cell lines. As with monastrol, flow cytometry analyses showed that the 20e and 20h compounds induced cell cycle arrest in the G2/M phase, and immunocytochemistry essays revealed the formation of monopolar spindles due to Eg5 inhibition without any toxicity to Caenorhabditis elegans.
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Rathke
, (1887)
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Versatility of the Biginelli reaction: Synthesis of new biphenyl dihydropyrimidin-2-thiones using different ketones as building blocks
Gon?alves, Itamar Luís,Davi, Leonardo,Rockenbach, Liliana,das Neves, Gustavo Machado,Kagami, Luciano Porto,Canto, R?mulo Faria Santos,Figueiró, Fabrício,Battastini, Ana Maria Oliveira,Eifler-Lima, Vera Lucia
, p. 2759 - 2762 (2018)
A multi-component synthesis of biphenyl dihydropyrimidin-2-thiones from 1-phenylthiourea, aldehydes and ketones or di-ketones has been demonstrated. The reaction proceeded well for aldehydes with electron donor or acceptor substituents under mild conditions.
A simple and convenient synthesis of isolated fused heterocycles based on: 6-Phenyl-2-thioxo-2,3-dihydropyrimidin-4(5H)-one and 5-acetyl-6-phenyl-2-thioxo-2,3-dihydropyrimidin-4(5H)-one
Abdel Reheim, Mohamed Ahmed Mahmoud,Abdel Hafiz, Ibrahim Saad,Elian, Mohamed Ahmed
, p. 1397 - 1414 (2016)
The reaction of 6-phenyl-2-thioxo-2,3-dihydropyrimidin-4(5H)-one 1 with acetyl chloride in acetic anhydride in the presence of sodium acetate afforded 5-acetyl-6-phenyl-2-thioxo-2,3-dihydropyrimidin-4(5H)-one 2 which reacted with bromine, hydrazine hydrate, phenylhydrazine, cyanothioacetamide, aldehydes and (malononitrile/sulfur) to give 2-thioxo-2,3-dihydropyrimidine derivatives 4, 7a,b, 8, 10 and 11 respectively. In the present investigation 6-phenyl-2-thioxo-2,3-dihydropyrimidin-4(5H)-one 1 was reacted with chloroacetyl chloride to yield the corresponding compound 13. Compound 1 was reacted with some electrophilic reagents such as (benzylidene-cyanothioacetamide derivatives, 2-cyano-2-cyclopentylethanethioamide, 2-cyano-2-cyclohexylethanethioamide and aromatic diazonium salts) to give compounds 23, 27a,b and 35 respectively. The newly synthesized heterocycles were characterized on the basis of their chemical properties and spectral data.
Development of S-Substituted Thioisothioureas as Efficient Hydropersulfide Precursors
Khodade, Vinayak S.,Toscano, John P.
, p. 17333 - 17337 (2018)
Because of their inherent instability, hydropersulfides (RSSH) must be generated in situ using precursors, but very few physiologically useful RSSH precursors have been developed to date. In this work, we report the design, synthesis, and evaluation of novel S-substituted thiosiothioureas as RSSH precursors. These water-soluble precursors show efficient and controllable release of RSSH under physiological conditions.
Grehn
, p. 267 (1977)
Synthesis of Novel Triazole Incorporated Thiazolone Motifs Having Promising Antityrosinase Activity through Green Nanocatalyst CuI-Fe3O4@SiO2 (TMS-EDTA)
Darroudi, Mahdieh,Ranjbar, Sara,Esfandiar, Mohammad,Khoshneviszadeh, Mahsima,Hamzehloueian, Mahshid,Khoshneviszadeh, Mehdi,Sarrafi, Yaghoub
, (2020)
In the present work, novel 5-((1-benzyl-1,2,3-triazol-4-yl)methoxybenzylidene)-2-(arylamino)thiazol-4-one thiazolone incorporated triazole derivatives have been designed as tyrosinase inhibitors. The compounds were synthesized through click reaction in good yield. Moreover, the antityrosinas activity of the synthesized derivatives was evaluated. In the search for establishing a click copper-catalyzed azide/alkyne cycloaddition (CuAAC) reaction under strict conditions, in terms of a novel air-stable, a recyclable and efficient magnetic catalyst was planned for new triazole derivatives as a well-organized copper iodide supported on the functionalized Fe3O4@SiO2 core-shell (CuI/Fe3O4@SiO2(TMS-EDTA) nanoparticles). The engineered nanocatalyst synthesized for the first time and characterized by different methods, including FT-IR spectroscopy, XRD, FESEM, EDX, TEM, TGA, and BET analysis. The excellent catalytic performance in ethanol with high surface area (351.7 m2g?1) and short reaction time for diverse functional groups (120–200 min), no use of toxic solvents, reusability of the catalyst, and using eco-friendly conditions are the advantageous of this work. Moreover,the nanocatalyst can be used at least five times without any significant decrease in the yield of the reaction. The thiazolidine-triazole derivatives 9a, 9c, 9e, and 9 g showed promising tyrosinase inhibitory activity with IC50 values in the range of 5.90–9.81 μM. The compounds were found to be considerably more potent tyrosinase inhibitors than the reference inhibitor kojic acid (IC50 = 18.36 μM).
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Fokin,A.V. et al.
, (1974)
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Design, synthesis, and antipoliferative activities of novel substituted imidazole-thione linked benzotriazole derivatives
El-Malah, Afaf,Khayyat, Ahdab N.,Malebari, Azizah M.,Mohamed, Khaled O.
, (2021/10/12)
A new series of benzotriazole moiety bearing substituted imidazol-2-thiones at N1 has been designed, synthesized and evaluated for in vitro anticancer activity against the different cancer cell lines MCF-7(breast cancer), HL-60 (Human promyelocytic leukemia), and HCT-116 (colon cancer). Most of the benzotriazole analogues exhibited promising antiproliferative activity against tested cancer cell lines. Among all the synthesized compounds, BI9 showed potent activity against the cancer cell lines such as MCF-7, HL-60 and HCT-116 with IC50 3.57, 0.40 and 2.63 μM, respectively. Compound BI9 was taken up for elaborate biological studies and the HL-60 cells in the cell cycle were arrested in G2/M phase. Compound BI9 showed remarkable inhibition of tubulin polymerization with the colchicine binding site of tubulin. In addition, compound BI9 promoted apoptosis by regulating the expression of pro-apoptotic protein BAX and anti-apoptotic proteins Bcl-2. These results provide guidance for further rational development of potent tubulin polymerization inhibitors for the treatment of cancer.
Eco-efficient one-pot tandem synthesis of 1-aryl-1H-tetrazol-5-amine by CAN via in situ generated 1-phenylthiourea and heterocumulene
Kondhare, Dasharath D.,Bhadke, Venkat V.,Deshmukh, Sushma S.,Wakhradkar, Mahesh G.,Totawar, Balaji B.
, (2021/07/28)
A simple, cost-effective, environmentally benign, and efficient one-pot tandem approach to the synthesis of pharmaceutically important 1-aryl-1H-tetrazole-5-amines 3a-k and 4a-k has been described. The reaction utilized 1-phenyl thiourea, which was generated in situ from aqueous ammonia and isocyanates 1a-k, for the formation of heterocumenes using sodium azide, triethylamine, and ceric ammonium nitrate (CAN) to obtain various aryl-substituted 1H-tetrazole-5-amines (3a-k) in good to excellent yields.
Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea
Bagherzadeh, Nastaran,Sardarian, Ali Reza,Inaloo, Iman Dindarloo
supporting information, p. 11852 - 11858 (2021/07/12)
An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.
