31979-23-4Relevant academic research and scientific papers
Promising bio-active complexes of platinum(II) and palladium(II) derived from heterocyclic thiourea: Synthesis, characterization, DFT, molecular docking, and anti-cancer studies
Al-Janabi, Ahmed S.,Al-Jibori, Subhi A.,Alqahtani, Ali S.,Faihan, Ahmed S.,Hatshan, Mohammad R.,Kadhim, Mustafa M.,Nasr, Fahd A.,Saleh, Abdulrahman M.
, (2021/12/30)
Four Platinum(II) and Palladium(II) heterocyclic thiourea complexes have been prepared; [Pt(CPPT)2](1), [Pd(CPPT)2](2), [Pt(MPPT)2](3), and [Pd(MPPT)2](4) (Where HCPPT=1-(5-chloropyridin-2-yl)-3-phenylthiourea,
Design and synthesis of thiourea-based derivatives as Mycobacterium tuberculosis growth and enoyl acyl carrier protein reductase (InhA) inhibitors
Krishna, Vagolu Siva,Lherbet, Christian,Sriram, Dharmarajan,Do?an, ?engül Dilem,Do?an, Hilal,Gündüz, Miyase G?zde
, (2020/05/18)
Tuberculosis remains the most deadly infectious disease worldwide due to the emergence of drug-resistant strains of Mycobacterium tuberculosis. Hence, there is a great need for more efficient treatment regimens. Herein, we carried out rational molecular modifications on the chemical structure of the urea-based co-crystallized ligand of enoyl acyl carrier protein reductase (InhA) (PDB code: 5OIL). Although this compound fulfills all structural requirements to interact with InhA, it does not inhibit the enzyme effectively. With the aim of improving the inhibition value, we synthesized thiourea-based derivatives by one-pot reaction of the amines with corresponding isothiocyanates. After the structural characterization using 1H NMR, 13C NMR, FTIR and HRMS, the obtained compounds were initially tested for their abilities to inhibit Mycobacterium tuberculosis growth. The results revealed that some compounds exhibited promising antitubercular activity, MIC values at 0.78 and 1.56 μg/mL, combined with low cytotoxicity. Moreover, the most active compounds were tested against latent as well as dormant forms of the bacteria utilizing nutrient starvation model and Mycobacterium tuberculosis infected macrophage assay. Enzyme inhibition assay against enoyl-acyl carrier protein reductase identified InhA as the important target of some compounds. Molecular docking studies were performed to correlate InhA inhibition data with in silico results. Finally, theoretical calculations were established to predict the physicochemical properties of the most active compounds.
Synthesis and in vitro urease inhibitory activity of N,N′- disubstituted thioureas
Khan, Khalid Mohammed,Naz, Farzana,Taha, Muhammad,Khan, Ajmal,Perveen, Shahnaz,Choudhary,Voelter, Wolfgang
, p. 314 - 323 (2014/02/14)
Thiourea derivatives (1-38) were synthesized and evaluated for their urease inhibition potential. The synthetic compounds showed a varying degree of in vitro urease inhibition with IC50 values 5.53 ± 0.02-91.50 ± 0.08 μM, most of which are superior to the standard thiourea (IC50 = 21.00 ± 0.11 μM). In order to ensure the mode of inhibition of these compounds, the kinetic study of the most active compounds has been carried out. Most of these inhibitors were found to be mixed-type of inhibitors, except compounds 13 and 30 which were competitive, while compound 19 was identified as non-competitive inhibitor with Ki values between 8.6 and 19.29 μM.
2-aminothiazoles as therapeutic leads for prion diseases
Gallardo-Godoy, Alejandra,Gever, Joel,Fife, Kimberly L.,Silber, B. Michael,Prusiner, Stanley B.,Renslo, Adam R.
experimental part, p. 1010 - 1021 (2011/04/25)
2-Aminothiazoles are a new class of small molecules with antiprion activity in prion-infected neuroblastoma cell lines (J. Virol. 2010, 84, 3408). We report here structure-activity studies undertaken to improve the potency and physiochemical properties of 2-aminothiazoles, with a particular emphasis on achieving and sustaining high drug concentrations in the brain. The results of this effort include the generation of informative structure-activity relationships (SAR) and the identification of lead compounds that are orally absorbed and achieve high brain concentrations in animals. The new aminothiazole analogue (5-methylpyridin-2-yl)-[4-(3-phenylisoxazol-5-yl)-thiazol-2-yl]-amine (27), for example, exhibited an EC50 of 0.94 μM in prion-infected neuroblastoma cells (ScN2a-cl3) and reached a concentration of ～25 μM in the brains of mice following three days of oral administration in a rodent liquid diet. The studies described herein suggest 2-aminothiazoles as promising new leads in the search for effective therapeutics for prion diseases.
Fused polycyclic nitrogen-containing heterocycles : 1117. 4-Hydroxy-3-phenyl-2-(2-pyridylimino)-and 4-hydroxy-2-phenyl-3-(2-pyridyl) thiazolidines and related thiazolo[3,4-a]quinoxalines
Mamedov,Zhukova,Beschastnova,Levin,Gubaidullin,Litvinov
, p. 2308 - 2314 (2008/09/18)
The condensation of methyl phenylchloropyruvate with 1-phenyl-3-(2-pyridyl) thiourea and its 3-and 4-picolyl homologs affords the corresponding 4-hydroxythiazolidines, which react with o-phenylenediamine to give one of two possible thiazolo[3,4-a]quinoxalines containing the pyridyl-or picolylimine substituents at position 1. 3a-Hydroxy-3-phenylimino-1-(2-pyridyl)thiazolo[3,4- a]quinoxalin-4-(3H,5H)-one, which is a covalent hydrate of the final product, was isolated as an intermediate in this reaction.
Structural, spectral and thermal studies of substituted N-(2-pyridyl)-N′-phenylthioureas
Valdés-Martínez, Jesús,Hernández-Ortega, Simón,Espinosa-Pérez, Georgina,Presto, Carmina A,Hermetet, Anne K,Haslow, Kristin D,Ackerman, Lily J,Szczepura, Lisa F,Goldberg, Karen I,Kaminsky, Werner,West, Douglas X
, p. 77 - 87 (2007/10/03)
N-2-(3-picolyl)-N′-phenylthiourea, 3PicTuPh, monoclinic, P21/n, a = 7.617(2) b = 7.197(5), c = 22.889(5) ?, β = 94.63(4)°, V = 1250.7(1) ?3 and Z = 4; N-2-(4-picolyl)-N′-phenylthiourea, 4PicTuPh, triclinic, P-1, a = 7.3960(5), b = 7.
Molecular Conformation of N,N'-Diarylthioureas: an Assessment by 1H NMR and Infrared Spectroscopy
Sudha, L. V.,Manogaran, S.,Sathyanarayana, D. N.
, p. 591 - 596 (2007/10/02)
Several N,N'-dipyridyl- and N-phenyl-N'-pyridyl-thioureas were examined in different solvents at various temperatures by 1H NMR in order to study their conformational properties.The influence of concentration and the methyl substituent in the pyridine ring on the chemical shifts of the NH and pyridine groups was investigated.The observed chemical shifts are analysed in terms of the conformational properties of the molecules.Free energy barriers to the internal rotation about the C-N bonds have been determined.Infrared spectra have been measured to supplement the NMR studies.Intramolecular hydrogen bonding played a major role in the preferred conformation of pyridylthioureas.The data further revealed an interesting dynamic exchange phenomenon occuring in symmetric N,N'-dipyridylthioureas between two intramolecularly hydrogen bonded conformers.
