66090-34-4Relevant articles and documents
Bioactivity of new ferrocene incorporated N,N′-disubstituted ureas: Synthesis, structural elucidation and DFT study
Asghar, Faiza,Badshah, Amin,Lal, Bhajan,Butler, Ian S.,Tabassum, Saira,Tahir, Muhammad Nawaz
, p. 82 - 91 (2016)
We report here the synthesis, structural characterization and biological assessment of three new ferrocene incorporated ureas (1-3). The synthesis of these complexes was accomplished by the deprotection of ferrocene-based thioureas to the corresponding oxo analogues using NaOH(aq) and mercuric chloride. The new ferrocenyl ureas were characterized by FT-IR, multinuclear (1H and 13C) NMR, AAS and elemental analysis. Furthermore, the single-crystal X-ray structure of compound 2 was also determined. The DNA binding potency of these ureas was evaluated by UV-Vis spectroscopy and cyclic voltammetry (CV). The three complexes interact electrostatically with DNA and have impressive binding constants ranging from 3.42 × 104 to 8.15 × 104 M-1. The diffusion coefficients of the drug-DNA adducts are lower than is that for the free drug indicating the formation of a high molecular weight complex that diffuses slowly towards the electrode. The small binding site size of 0.509 (1), 0.528 (2) and 0.473 (3) base pairs is also indicative of an electrostatic mode of interaction. The DFT calculated HOMO and LUMO energies correlate well with the experimentally determined redox potential values. The synthesized ureas (1-3) were screened for their antibacterial, antifungal and protein kinase inhibition potency. These compounds play a significant role in arresting microbial growth and are potent protein kinase inhibitors.
Synthesis, kinetics and biological assay of some novel aryl bis-thioureas: A potential drug candidates for Alzheimer's disease
Abbas, Qamar,Abd-Rabboh, Hisham S. M.,Bahadur, Ali,Channar, Kashif Ali,Channar, Pervaiz Ali,Hassan, Mubashir,Iqbal, Shahid,Khan, Bilal Ahmad,Kim, Jung Min,Lal, Bhajan,Mahesar, Parvez Ali,Nawaz, Muhammad,Rajoka, Muhammad Shahid Riaz,Rashid, S. G.,Raza, Hussain,Saeed, Aamer,Shah, Mazloom,Siyal, Ali Nawaz,Ujan, Rabail
, (2021/08/03)
A new series of bis-thioureas (4a-4j) was synthesized and characterized through spectroscopic and elemental analysis. The synthesized compounds 4a-4j were subjected to acetylcholinesterase enzyme (AChE) inhibition activity and free radical scavenging activity. The results of AChE inhibition assay were found to be active in inhibiting the target enzyme with different IC50 values. Among all derivatives, the 4 g showed highly potent inhibition potential against AChE enzyme with IC50 value of 0.1761±0.00768 μM, which is several times better than the reference inhibitor neostigmine methylsulfate IC50 2.469±0.069 μM. The initial structure-activity relationship (SAR) of 4 g revealed dual hydrogen bonding ability (donor and acceptor). Moreover, the electronic environment around the aromatic ring also greatly influenced the enzyme inhibition of AChE. To further explore the newly synthesized AChE inhibitors, kinetic studies were carried out to determine the mode of inhibition and it was found to be competitive inhibition. Pharmacokinetic predictions (ADMET parameters) were also evaluated and compounds showed good lead-like potential with little hepatotoxic and no skin-sensitive effects. The molecular docking studies delineated the binding affinity of the ligands with target protein and showed docking scores in the range of -10.3 to -7.6 kcal/mol.
Benzoylthioureas: Design, synthesis and antimycobacterial evaluation
Abreu, Lethícia O.,Bispo, Marcelle L. F.,Brito, Tiago O.,Gomes, Karen M.,Louren?o, Maria C. S.,Macedo, Fernando,Pereira, Patricia M. L.,Tisher, Cesar A.,Yamada-Ogatta, Sueli F.,de Fátima, ?ngelo
, p. 93 - 103 (2020/02/04)
Background: New drugs and strategies to treat tuberculosis (TB) are urgently needed. In this context, thiourea derivatives have a wide range of biological activities, including anti-TB. This fact can be illustrated with the structure of isoxyl, an old anti-TB drug, which has a thiourea as a pharmacophore group. Objective: The aim of this study is to describe the synthesis and the antimycobacterial activity of fifty-nine benzoylthioureas derivatives. Methods: Benzoylthiourea derivatives have been synthesized and evaluated for their activity against Mycobacterium tuberculosis using the MABA assay. After that, a structure-activity relationship study of this series of compounds has been performed. Results and Discussion: Nineteen compounds exhibited antimycobacterial activity between 423.1 and 9.6 μM. In general, we observed that the presence of bromine, chlorine and t-Bu group at the para-position in benzene ring plays an important role in the antitubercular activity of Series A. These substituents were fixed at this position in benzene ring and other groups such as Cl, Br, NO2 and OMe were introduced in the benzoyl ring, leading to the derivatives of Series B. In general, Series B was less cytotoxic than Series A, which indicates that the presence of a substituent at benzoyl ring contributes to an improvement in both antimycobacterial activity and toxicity profiles. Conclusion: Compound 4c could be considered a good prototype to be submitted to further structural modifications in the search for new anti-TB drugs, since it is 1.8 times more active than the first line anti-TB drug ethambutol and 0.65 times less active than isoxyl.
Synthesis, characterization and biological activity of some dithiourea derivatives
Frost, Carminita,Hoppe, Heinrich,Hosten, Eric,Isaacs, Michelle,Khanye, Setshaba D.,Krause, Jason,Lobb, Kevin,Odame, Felix,Sayed, Yasien,Tshentu, Zenixole
, p. 764 - 777 (2020/10/02)
Novel dithiourea derivatives have been designed as HIV-1 protease inhibitors using Autodock 4.2, synthesized and characterized by spectroscopic methods and microanalysis. 1-(3-Bromobenzoyl)-3-[2-({[(3-bromophenyl)formami-do]methanethioyl}amino)phenyl]thio
