54001-07-9Relevant articles and documents
Phenylthiazoles with nitrogenous side chain: An approach to overcome molecular obesity
Elsebaei, Mohamed M.,Abutaleb, Nader S.,Mahgoub, Abdulrahman A.,Li, Daoyi,Hagras, Mohamed,Mohammad, Haroon,Seleem, Mohamed N.,Mayhoub, Abdelrahman S.
, (2019)
A novel series of phenylthiazoles bearing cyclic amines at the phenyl-4 position was prepared with the objective of decreasing lipophilicity and improving the overall physicochemical properties and pharmacokinetic profile of the compounds. Briefly, the pi
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.
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
, (2019/11/03)
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.
Synthesis, Characterization, and Antimicrobial Screening of 4″-methyl-2,2″-diaryl-4,2′:4′,5″-terthiazole Derivatives
Nalawade, Jitendra,Mhaske, Pravin C.,Shinde, Abhijit,Patil, Sachin V.,Choudhari, Prafulla B.,Bobade, Vivek D.
, p. 1366 - 1374 (2018/04/25)
A series of novel 4″-methyl-2,2″-diaryl-4,2′:4′,5″-terthiazole (8a-p) derivatives has been synthesized and screened for antibacterial activity against four pathogenic bacteria, Escherichia coli, Pseudomonas flurescence, Staphylococcus aureus, and Bacillus subtilis. Among them, compounds 8a and 8j exhibited excellent antibacterial activity with minimum inhibitory concentration range of 1.0 to 5.3?μg/mL and compounds 8m and 8p exhibited moderate to good antibacterial activity with minimum inhibitory concentration range of 16.9 to 29.7?μg/mL against all tested strains. All the synthesized compounds were screened for their in vitro antifungal activity against Cocinida candida. Most of the compounds reported moderate antifungal activity. This study provides valuable directions to our ongoing endeavor of rationally designing more potent antimicrobial agent.
Synthesis, antitubercular and antimicrobial potential of some new thiazole substituted thiosemicarbazide derivatives
Abhale, Yogita K.,Shinde, Abhijit,Deshmukh, Keshav K.,Nawale, Laxman,Sarkar, Dhiman,Mhaske, Pravin C.
, p. 2557 - 2567 (2017/10/06)
The increase in antibiotic resistance due to multiple factors has warranted the need for search of new compounds which are active against multidrug resistant pathogens. In this context a small focused library of thiosemicarbazide derivatives of 2-arylthiazole-4-carbaldehyde, 4-methyl-2-arylthiazole-5-carbaldehyde and 1-(4-methyl-2-arylthiazol-5-yl) ethanone, (5a–l) has been synthesized. The title compounds were screened for inhibitory activity against Mycobacterium tuberculosis H37Ra (ATCC 25177) and Mycobacterium bovis Bacille Calmette Guerin (ATCC 35743) strains. The synthesized compounds, 5a–l were further assayed for their cytotoxic activity against the two human cancer cell lines, HeLa and human colon carcinoma 116 cell lines and showed no significant cytotoxic activity against these two cell lines at the maximum concentration evaluated. Further, the synthesized compounds were found to have potential antibacterial activity against Gram-negative bacteria, Escherichia coli, Pseudomonas flurescence and Gram-positive bacteria, Staphylococcus aureus, Bacillus subtilis. Most of the synthesized compounds showed moderate activity against fungal strain Candida albicans. This study provides valuable directions to our ongoing endeavor of rationally designing more potent antimycobacterial agent.
Fused Heterocycles: Synthesis and Antitubercular Activity of Novel 6-Substituted-2-(4-methyl-2-substituted phenylthiazol-5-yl)H-imidazo[1,2-a]pyridine
Abhale, Yogita K.,Deshmukh, Keshav K.,Sasane, Amit V.,Chavan, Abhijit P.,Mhaske, Pravin C.
, p. 229 - 233 (2015/03/18)
(Chemical Equation Presented) A series of 6-substituted-2-(4-methyl-2-substituted phenylthiazol-5-yl)H-imidazo[1,2-a]pyridine derivatives 4a-4l is described. The antitubercular activity of the synthesized compounds was determined against Mycobacterium smegmatis MC2 155 strain. From the activity result, it was found that the phenyl or 4-fluorophenyl group at 2 position of thiazole nucleus and bromo substituent at 6 position of imidazo[1,2-a]pyridine showed good antitubercular activity.
Synthesis and biological screening of 2′-aryl/benzyl-2-aryl-4-methyl-4′,5-bithiazolyls as possible anti-tubercular and antimicrobial agents
Abhale, Yogita K.,Sasane, Amit V.,Chavan, Abhijit P.,Deshmukh, Keshav K.,Kotapalli, Sudha Sravanti,Ummanni, Ramesh,Sayyad, Sadikali F.,Mhaske, Pravin C.
, p. 340 - 347 (2015/03/18)
A series of 2′-aryl/benzyl-2-aryl-4-methyl-4′,5-bithiazolyl derivatives, 25-64 were synthesized and evaluated for inhibitory activity against Mycobacterium smegmatis MC2 155 strain and antimicrobial activities against four pathogenic bacteria Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Proteus vulgaris. Among them, compounds 40, 49, 50, and 54 exhibited moderate to good inhibition on the growth of the bacteria Mycobacterium smegmatis at the concentration of 30 μM. Compounds 26, 40, 44, 54 and 56 exhibited moderate to good antibacterial activity. Compound 5-(2′-(4-fluorobenzyl)thiazol-4′-yl)-2-(4-fluorophenyl)-4-methyl-thiazole (54) exhibited both antitubercular as well as antimicrobial activity against all tested strains.
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.
Design, synthesis, and biological evaluation of thiazoles targeting flavivirus envelope proteins
Mayhoub, Abdelrahman S.,Khaliq, Mansoora,Kuhn, Richard J.,Cushman, Mark
experimental part, p. 1704 - 1714 (2011/05/05)
A series of third-generation analogues of methyl 4-(dibromomethyl)-2-(4- chlorophenyl)thiazole-5-carboxylate (1), which had the most potent antiviral activity among the first- and second-generation compounds, have been synthesized and tested against yellow fever virus using a cell-based assay. The compounds were designed with the objectives of improving metabolic stability, therapeutic index, and antiviral potency. The biological effects of C4 and C5 substitution were examined. The methylthio ester and the dihydroxypropylamide analogues had the best antiviral potencies and improved therapeutic indices and metabolic stabilities relative to the parent compound 1.
