54001-06-8Relevant academic research and scientific papers
Potent ribonucleotide reductase inhibitors: Thiazole-containing thiosemicarbazone derivatives
Ertas, Merve,Sahin, Zafer,Bulbul, Emre F.,Bender, Ceysu,Biltekin, Sevde N.,Berk, Barkin,Yurttas, Leyla,Nalbur, Aysu M.,Celik, Hayati,Demirayak, ?eref
, (2019)
The antioxidant, antimalarial, antibacterial, and antitumor activities of thiosemicarbazones have made this class of compounds important for medicinal chemists. In addition, thiosemicarbazones are among the most potent and well-known ribonucleotide reductase inhibitors. In this study, 24 new thiosemicarbazone derivatives were synthesized, and the structures and purity of the compounds were determined by IR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis. The IC50 values of these 24 compounds were determined with an assay for ribonucleotide reductase inhibition. Compounds 19, 20, and 24 inhibited ribonucleotide reductase enzyme activity at a higher level than metisazone as standard. The cytotoxic effects of these compounds were measured on the MCF7 (human breast adenocarcinoma) and HEK293 (human embryonic kidney) cell lines. Similarly, compounds 19, 20, and 24 had a selective effect on the MCF7 and HEK293 cell lines, killing more cancer cells than cisplatin as standard. The compounds (especially 19, 20, and 24 as the most active ones) were then subjected to docking experiments to identify the probable interactions between the ligands and the enzyme active site. The complex formation was shown qualitatively. The ADME (absorption, distribution, metabolism, and excretion) properties of the compounds were analyzed using in-silico techniques.
Novel cyanothiouracil and cyanothiocytosine derivatives as concentration-dependent selective inhibitors of U87MG glioblastomas: Adenosine receptor binding and potent PDE4 inhibition
Sahin, Zafer,Biltekin, Sevde Nur,Yurttas, Leyla,Berk, Barkin,?zhan, Ya?mur,Sipahi, Hande,Gao, Zhan-Guo,Jacobson, Kenneth A.,Demirayak, ?eref
, (2021/01/12)
Thiouracil and thiocytosine are important heterocyclic pharmacophores having pharmacological diversity. Antitumor and antiviral activity is commonly associated with thiouracil and thiocytosine derivatives, which are well known fragments for adenosine receptor affinity with many associated pharmacological properties. In this respect, 33 novel compounds have been synthesized in two groups: 24 thiouracil derivatives (4a-x) and 9 thiocytosine derivatives (5a-i). Antitumor activity of all the compounds was determined in the U87 MG glioblastoma cell line. Compound 5e showed an anti-proliferative IC50 of 1.56 μM, which is slightly higher activity than cisplatin (1.67 μM). The 11 most active compounds showed no signficant binding to adenosine A1, A2A or A2B receptors at 1 μM. Brain tumors express high amounts of phosphodiesterases. Compounds were tested for PDE4 inhibition, and 5e and 5f showed the best potency (5e: 3.42 μM; 5f: 0.97 μM). Remakably, those compounds were also the most active against U87MG. However, the compounds lacked a cytotoxic effect on the HEK293 healthy cell line, which encourages further investigation.
Versatile approaches to a library of building blocks based on 5-acylthiazole skeleton
Kulyk, Olesia G.,Biloborodov, Dmytro A.,Cherevatenko, Maksim A.,Shyriakin, Yevhen Y.,Lyapunov, Alexander Yu.,Mazepa, Alexander V.,Vashchenko, Valerii V.,Orlov, Valeriy D.,Kolosov, Maksim A.
supporting information, p. 3616 - 3628 (2020/09/07)
Thiazole derivatives represent an important class of azole heterocycles with a broad spectrum of biological activity and, therefore, the synthesis of these compounds is of remarkable concern. We present here practical and reliable protocol for synthesis of some 5-acylthiazoles and demonstrate their utility in the preparation of several new series of thiazole-containing building blocks through transformation of 5-acyl function. Specifically, thiazole-based alcohols, oximes, primary, and secondary amines were successively synthesized in good to excellent yields. The chemical structures of obtained compounds were confirmed by 1H and 13C NMR-spectroscopy, elemental analysis, and mass-spectrometry.
A facile and eco-friendly synthesis of diarylthiazoles and diarylimidazoles in water
Kumar, Dalip,Kumar, N. Maruthi,Patel, Gautam,Gupta, Sudeep,Varma, Rajender S.
experimental part, p. 1983 - 1986 (2011/04/25)
A simple, efficient and high yielding greener protocol for the synthesis of substituted thiazoles and imidazoles is described that utilizes the reaction of readily available α-tosyloxy ketones with variety of thioamides/amidines in water.
Synthesis and microbial activity of new thiazolyl 1,4-benzothiazines
Dengle,Ingle,Bondge,Mane
, p. 390 - 393 (2007/10/03)
5-Acyl-2-aryl-4-methyl thiazoles 1 have been converted to 1-(2'-aryl- 4'-methylthiazol-5'-yl)-3-aryl-2-propen-1-ones 2 by Claisen-Schmidt condensation. The chalcones 2 are brominated to give their bromo derivatives 3 which on hydrolysis yield 1-(2'-aryl-4
Solid state synthesis of 2-aroylbenzo[b]furans, 1,3-thiazoles and 3-aryl-5,6-dihydroimidazo[2,1-b][1,3]thiazoles from α-tosyloxyketones using microwave irradiation
Varma, Rajender S.,Kumar, Dalip,Liesen, Per J.
, p. 4093 - 4096 (2007/10/03)
The expeditious solventless syntheses of 2-aroylbenzo[e]furans, 1,3-thiazoles and 3-aryl-5,6-dihydroimidazo[2,1-b]-[1,3]thiazoles are described from readily accessible α-tosyloxyketones and mineral oxides in processes that are accelerated by exposure to m
