thiourea and derivatives

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Design, Synthesis, and Docking Study of Acyl Thiourea Derivatives as Possible Histone Deacetylase Inhibitors with a Novel Zinc Binding Group

Design, Synthesis, and Docking Study of Acyl Thiourea Derivatives as Possible Histone Deacetylase Inhibitors with a Novel Zinc Binding Group

Abstract: Histone deacetylase inhibitors with zinc binding groups often exhibit drawbacks like non-selectivity or toxic effects. Thus, there are continuous efforts to modify the currently available inhibitors or to discover new derivatives to overcome these problems. One approach is to synthesize new compounds with novel zinc binding groups. The present study describes the utilization of acyl thiourea functionality, known to possess the ability to complex with metals, to be a novel zinc binding group incorporated into the designed histone deacetylase inhibitors. N-adipoyl monoanilide thiourea (4) and N-pimeloyl monoanilide thiourea (5) have been synthesized and characterized successfully. They showed inhibition of growth of human colon adenocarcinoma and mouse hepatoblastoma cells with low cytotoxic effect against normal human breast cells. Their binding mode to the active site of several histone deacetylases has been studied by docking and the results gave a preliminary indication that they could be successful histone deacetylase inhibitors.
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Design, Synthesis and Bioevaluation of New Urea/Thiourea Derivatives of 3,5 dichloro 4 hydroxy aniline

Design, Synthesis and Bioevaluation of New Urea/Thiourea Derivatives of 3,5 dichloro 4 hydroxy aniline

The antifungal strains, Aspergillus niger, Candida albicans and Fusarium oxysporum were used to investigate antifungal potency of the newly synthesized urea and thiourea derivatives 3(a-j) using the agar disc-diffusion method [35-38]. The fungal strains were maintained in Potato Dextrose Agar (PDA) medium (Hi-Media), a loopful of culture from the slant was inoculated in to the potato dextrose broth and incubated at 37°C for 48-72 h. Then 0.1 ml of the culture was spread on the potato dextrose agar plate and a sterile glass spreader was used for even distribution of the inoculum. All the compounds were dissolved in DMSO. Sterile discs of Whatman No.1 filter paper of about 6 mm diameter were impregnated on the surface of the media. Blank test showed that DMSO does not affect the growth of the test organisms. 100 μg/ml concentration of the test compounds were prepared and applied on the discs and incubated at 37°C for 48-72 h. The zone of inhibition around the disc was calculated as the edge to edge zone of the confluent growth in millimeters. All tests were repeated three times and the average data was taken as the final result. Nystatin was used as a reference drug and the inhibition zones of the test compounds were compared with controls (Table 6).
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Synthesis, docking study and biological evaluation of some new thiourea derivatives bearing benzenesulfonamide moiety

Synthesis, docking study and biological evaluation of some new thiourea derivatives bearing benzenesulfonamide moiety

The molecular model of the new thiourea derivatives was done using MOE software suite 10.2008. Follow- ing geometry optimization, a systematic conformational search was carried out to RMS gradient of 0.05 Å with energy minimization of the resultant conformations employing the ConfSearch module implemented in MOE. All molecular mechanics computations were per- formed with the Merck Force Field (MMFF94s). The crys- tallographic structure of M. tuberculosis enoyl reductase InhA in complex with N-{1-[(2-chloro-6-fluorophenyl) methyl]-1H-pyrazol-3-yl]-5-[(1S)-1-(3-methyl-1H-pyra- zol-1-yl)ethyl]-1,3,4-thiadiazol-2-amine (GSK 625) was obtained from the Protein Data Bank (PDB ID: 5JFO). Water molecules were ignored and hydrogen atoms were added to the enzyme and partial charges were calcu- lated. Validation followed by docking of the compounds into the active site were carried out, after removing the co-crystallized ligand. The target protein was kept rigid, while the ligands adopt 50 separate docking simulations using default parameters. The conformations were cho- sen based on their S score, and appropriate fitting with the relevant amino acids in the binding pocket.
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Corrosion Inhibition of Thiourea and Thiadiazole Derivatives : A Review

Corrosion Inhibition of Thiourea and Thiadiazole Derivatives : A Review

The continuous search for better corrosion inhibitors, due to vast differences in the media encountered in industry remains a focal point in corrosion control. The use of organic compounds to inhibit corrosion has assumed great significance due to their application in preventing corrosion under various corrosive environments. These compounds have great potential to inhibit aqueous corrosion due to film formation by adsorption on the metal surface. This paper reviews the inhibitive effect of thiourea and thiadiazole derivatives. This group of organosulphur and heterocyclic compounds and derivatives has important theoretical and practical applications, but their inhibition mechanism is not fully understood, despite extensive study. The effect of these compounds on the corrosion of metallic alloys was evaluated through assessment of various journals and experimental techniques. The corrosion rate was found to be a function of different variables. Due attention was paid to the systematic study of inhibitor action of derivatives with much emphasis on the functional groups of the molecular structure. From the comprehensive discourse presented, it is concluded that the derivatives fulfill the basic requirements for consideration as an efficient corrosion inhibitor.
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OXONE AND IODOBENZENE ARE USEFUL REACTION SYSTEM FOR SYNTHESIS OF 2 AMINOTHIAZOLE DERIVATIVES FROM EASILY AVAILABLE THIOUREA AND ALKYL / ARYL KETONES

OXONE AND IODOBENZENE ARE USEFUL REACTION SYSTEM FOR SYNTHESIS OF 2 AMINOTHIAZOLE DERIVATIVES FROM EASILY AVAILABLE THIOUREA AND ALKYL / ARYL KETONES

General Experimental Procedure for Synthesis of 2-aminothiazole Derivatives: Mixture of Oxone (614 mg, 2 mmol) and Iodobenzene (408 mg, 2 mmol) in aqueous acetonitrile stirred at room temperature for 10 min, followed by addition of catalytic amount of KBr (59 mg) under stirring at room temperature followed by addition of Acetophenone (1 mmol) and thiourea (2 mmol) under stirring at room temperature. The resultant reaction mixture was stirred at room temperature until the starting material was completely consumed (TLC). The reaction mixture was diluted with CH 2 Cl and washed successively with 10%
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SYNTHESIS AND ANTIOXIDANT ACTIVITY OF UREA AND THIOUREA DERIVATIVES OF GLY/PRO CONJUGATED 2, 3  DICHLOROPHENYL PIPERAZINE

SYNTHESIS AND ANTIOXIDANT ACTIVITY OF UREA AND THIOUREA DERIVATIVES OF GLY/PRO CONJUGATED 2, 3 DICHLOROPHENYL PIPERAZINE

Urea and thiourea are important functional groups in numerous natural products and drug intermediates, and are used as neutral receptor for various anions (anion complexation), 20 and building blocks for various heterocycles. Urea and thiourea derivatives possess many promising biological activities, such as herbicidal, [21] antimicrobial, [22] antioxidant, [23] antiviral, [24] anti-HIV [25] and antitumor activity, [26] while urea derivatives exhibit anti- inflammatory [27] , antimalarial [28] and antidiabetic activities. [29] These compounds could also be used for the detoxification of super antigens from body fluids and for the treatment of hemoglobinopathies in the cases of sickle cell anemia and Beta (β) thalassemia, [30]
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Synthesis and Preliminary Inhibition Study of Carbonyl Thiourea Derivatives on Corrosion of Mild Steel in Acidic Media

Synthesis and Preliminary Inhibition Study of Carbonyl Thiourea Derivatives on Corrosion of Mild Steel in Acidic Media

Three new thiourea derivatives namely N- benzoyl-N’-propylthiourea (TU1), N-butanoyl-N’-(4- flurophenyl)thiourea (TU2) and N-4-chlorobenzoyl- N’-(4-flurophenyl)thiourea (TU3), were successfully synthesized and characterized using spectroscopic methods. From the anticorrosion study, the synthesized thiourea derivatives (TU1, TU2 and TU3) have been found to display corrosion inhibition properties on mild steel in 1 M HCl. It is believed that these inhibitors form a protective layer on the metal surface and reduce further corrosion attack. The highest inhibition efficiency achieved was 96.08 % found at concentration of 0.0004 M in TU3. Meanwhile, the highest inhibition efficiency of 93.45 % and 88.71 % at the concentration of 0.0004 M were found in TU2 and TU1, respectively. As the concentration of the inhibitors increase, the corrosion inhibition efficiency also increased. TU3 is suggested to be the most efficient inhibitor compared to TU2 and TU1, due to the presence of two benzene rings in the molecule structure. As a conclusion, the corrosion inhibition efficiency of the compound depends on the several factors, such as the presence of electron donating group and pi-electron rich benzene ring in the molecular structure.
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Green synthesis of saccharin substituted urea and thiourea derivatives and their antimicrobial evaluation Rashmi Singh and Komal Jakhar*

Green synthesis of saccharin substituted urea and thiourea derivatives and their antimicrobial evaluation Rashmi Singh and Komal Jakhar*

A series of saccharin substituted urea and thiourea derivatives has been synthesized by reaction of differently substituted ureas and thioureas with saccharin under microwave irradiations using water as a non-toxic, non- flammable green solvent. The structure of the synthesized compounds has been confirmed by IR, 1 H NMR, mass and elemental analysis. The synthesized compounds have been evaluated for their antimicrobial activity against different bacterial and fungal strains using micro broth dilution assay. The compounds are further screened for drug likeliness and In silico ADMET analysis.
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 SYNTHESIS, PHARMACOLOGICAL EVALUATION AND LIGAND-PROTEIN INTERACTION STUDY OF HYBRID UREA AND THIOUREA DERIVATIVES AS ANTIHYPERGLYCEMIC AGENTS

 SYNTHESIS, PHARMACOLOGICAL EVALUATION AND LIGAND-PROTEIN INTERACTION STUDY OF HYBRID UREA AND THIOUREA DERIVATIVES AS ANTIHYPERGLYCEMIC AGENTS

compound 5d showed significant improvement of the body weight, blood glucose level, serum enzyme parameter, lipid profile as well as tissue antioxidant parameters. Further, molecular docking studies showed that these urea/thiourea derivatives were binding to the active site of α-glucosidase enzyme with the hydrophobic interactions, noncovalent and hydrogen bond interactions. The docking studies are in good agreement with the invitro and invivo studies. Hence, this study identified a new structural type of α-glucosidase inhibitors which could be used as the lead molecules for further research and development of potent α-glucosidase inhibitors for the treatment of diabetes.
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Synthesis and Antibacterial Activity of Urea and Thiourea Derivatives of Anacardic Acid Mixture Isolated from A Natural Product Cashew Nut Shell Liquid (CNSL)

Synthesis and Antibacterial Activity of Urea and Thiourea Derivatives of Anacardic Acid Mixture Isolated from A Natural Product Cashew Nut Shell Liquid (CNSL)

Synthesis and antibacterial activity of some novel urea and thiourea derivatives (8a - 8k, 9a - 9f) of anacardic acid pre- pared from commercially available anacardic acid which is obtained from natural product Cashew Nut Shell Liquid (CNSL). Compounds (8a - 8k, 9a - 9f) were tested for Gram positive and Gram negative bacterial cultures. Most of the compounds were showed active compared with standard drug ampicilline.

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Synthesis, Identification, Theoretical and Experimental Studies for Carbon Steel Corrosion Inhibition in Sea Water for New Urea and Thiourea Derivatives linkage to 5-Nitro Isatin Moiety

Synthesis, Identification, Theoretical and Experimental Studies for Carbon Steel Corrosion Inhibition in Sea Water for New Urea and Thiourea Derivatives linkage to 5-Nitro Isatin Moiety

This research includes synthesis of some new heterocyclic derivatives of 5-Nitroisatin namely 5-Nitro-3- (Ethyl imino acetate)-2-oxo indole (1), 5-Nitro-3-[(imino Aceto) urea]-2-oxo indole (2), 5-Nitro-3-[(imino Aceto)thiourea]-2-oxo indole (3), and 5-Nitro-3-[(imino Aceto) phenylthiourea]-2-oxo indole (4), and characterized by FTIR, 1 H-NMR and some physical properties. Theoretically, the inhibition efficiency

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Synthesis, Identification, Theoretical And Experimental Studies For Carbon Steel Corrosion Inhibition in Sea Water for New Urea and Thiourea Derivatives linkage to 5 Nitro Isatin Moiety

Synthesis, Identification, Theoretical And Experimental Studies For Carbon Steel Corrosion Inhibition in Sea Water for New Urea and Thiourea Derivatives linkage to 5 Nitro Isatin Moiety

This research includes synthesis of some new heterocyclic derivatives of 5-Nitroisatin namely 5-Nitro-3-(Ethyl imino acetate)-2-oxo indole (1), 5-Nitro-3-[(imino Aceto) urea]-2-oxo indole (2), 5-Nitro-3-[(imino Aceto)thiourea]-2-oxo indole (3), and 5-Nitro-3-[(imino Aceto) phenylthiourea]-2-oxo indole (4), and characterized by Fourier-transform infrared (FTIR) spectroscopy, Proton nuclear magnetic resonance ( 1 H-NMR) and some physical properties. Theoretically, the inhibition efficiency parameters with physical properties were calculated to ensure for possibility using these compounds as inhibitors. Experimentally, studying the chosen compound of the corrosion inhibition efficiency for carbon steel in 3.5% NaCl solution by isatin derivative is chosen theoretically as the best inhibitor using potentiodynamic polarization.
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Synthesis and antimicrobial evaluation of urea and thiourea derivatives of sulfonic acid

Synthesis and antimicrobial evaluation of urea and thiourea derivatives of sulfonic acid

Ureas and thioureas are significant organic compounds having a number of applications in industries, laboratories, automobiles, medicines, fertilizers, herbicides, insecticides, plant growth regulators and urinetharapy. Different urea and thiourea derivatives are known to posses various pharmacodynamic applications as antibacterial [21], antifungal [22], anticancer [23], antiinflammatory [24], antiviral [25], potent inhibitors of influenza virus neuraminidase [26], antihyperglycaemic [27], anti-melanoma [28], antitubercular [29] peptidomimetics [30], diuretics [31], antagonists of human vanilloid VR1 receptors [32], cytokinin analogous [33], and inhibitors of Murine receptor A and Murine receptor B [34].
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Synthesis and Characterization of Some New Derivatives of Thiourea and Study of Their Biological Activity

Synthesis and Characterization of Some New Derivatives of Thiourea and Study of Their Biological Activity

Thiourea is an organic compound that consists of carbon, nitrogen, sulfur, and hydrogen atoms obtained from ammonium thiocyanate. The main reactive group is –CONHCSNH–. All the biological activities of this class of compounds are because of thiourea functionality [1]. Thiourea, having a considerably wide range of applications .The properties of urea and thiourea differ significantly because of the difference in electronegativity between sulfur and oxygen. Thus, thiourea is a versatile reagent in organic synthesis. The main application of thiourea is in textile processing. In addition, thiourea is commonly employed as a source of sulfide, e.g. for converting alkyl halides to thiols [2]. Thioureas are also used as building blocks for pyrimidine derivatives. Thus, thioureas condense with β-dicarbonyl compounds. The amino group on the thiourea initially condenses with a carbonyl, followed by cyclization and tautomerization. Thioureamoiety has become intensely synthesized due to its ability to undergo structural modifications [3]. The existing of two units of reactive primary amine groups has made thiourea a suitable precursor for a synthesis of many new compounds [4]. Thiourea derivatives are well known to display a broad spectrum of applications in pharmaceutical industry due to their biological properties such as antiparasitic [5], anticancer [6], antioxidant [7], antibacterial [8], antifungal [9], and anti-HIV [10].
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QSAR Studies of Thiourea, Thiazolidinedione and Thioparabanic Acid Derivatives of 4-Aminoquinoline as Antimalarial Agents

QSAR Studies of Thiourea, Thiazolidinedione and Thioparabanic Acid Derivatives of 4-Aminoquinoline as Antimalarial Agents

All QSAR studies were performed in V-Life MDS software Version 3.520. A series of 24 thiourea, thiazolidinedione and thioparabanic acid derivatives of 4-aminoquinoline tested for their anti-malarial activity was selected for QSAR Studies (Table 1). Selection of molecules in the training set and test is a key and important feature of any QSAR model. Therefore the care was taken in such a way that biological activities of all compounds in test set lie within the maximum and minimum value range of biological activities of training set of compounds. A Uni-Column statistics for training set and test set were generated to check correctness of selection criteria for trainings and test set molecules (Table 4).
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Design, Synthesis and Evaluation of Some Novel 1-phenyl-3-(5-phenyl-1H-imidazol-1-yl) Thiourea Derivatives as Anti-HIV Agents

Design, Synthesis and Evaluation of Some Novel 1-phenyl-3-(5-phenyl-1H-imidazol-1-yl) Thiourea Derivatives as Anti-HIV Agents

Objective: In the present study, a series of nineteen compound of 1-phenyl-3-(5-phenyl- 1H-imidazol-1-yl) thiourea derivatives (5a-9b) were designed, synthesized, characterized by physicochemical and spectral data (IR, 1H NMR, and mass spectroscopy) and evaluated for their Anti-HIV activity with the aim to develop novel substituted imidazole derivatives with broad-spectrum chemotherapeutic properties. Methods: Compounds (5a-9b) were designed by using Glide 5.0 to carry out binding mode analysis of N-substituted imidazoles against reverse transcriptase enzyme of wild type as well as resistant strains of HIV-1 virus with PDB ID: 1RT2, synthesized by reacting various substituted anilines and substituted phenacyl bromides in four steps and evaluated their anti HIV activity as well as cytotoxicity assay through MTT colorimetric measure. Results: Compounds 6a, 6b, 6c, 6d, 7c, 9a and 9b being the most active exhibited therapeutic index that were >22.4, 31.1, 30.5, 51.5, 34.6, 30.5 and 85.6 compared to Zidovudine (AZT) having therapeutic index (TI) 514342.6. Compound 9b showed the highest docking score -12.47 in the active site of the HIV protein of 1RT2 as well better in vitro anti-HIV activity.
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Corrosion Inhibitive Effect of Synthesized Thiourea Derivatives on Mild Steel in a 15% HCl Solution

Corrosion Inhibitive Effect of Synthesized Thiourea Derivatives on Mild Steel in a 15% HCl Solution

In this study, the inhibitive performance of two synthesized thiourea derivatives, namely, 1-(3- mercapto-5-(pyridin-4-yl)-4H-1,2,4-triazol-4-yl)-3-phenylthiourea (MPTP), 1-(3-mercapto-5-(pyridin- 4-yl)-4H-1,2,4-triazol-4-yl)-3-(4-methoxyphenyl) thiourea (MPTMP) were studied for mild steel corrosion in a 15% HCl solution using weight loss measurements, potentiodynamic polarization, and electrochemical impedance spectroscopy (EIS) techniques. The inhibition efficiency of both the inhibitors increased with an increase in the concentration of inhibitor. The inhibitors MPTP and MPTMP show a corrosion inhibition efficiency of 94.3% and 96.8% respectively, in 50 ppm concentrations at 303 K. Polarization studies showed that both inhibitors studied were of a mixed type in nature. The adsorption of inhibitors on the mild steel surface obey the Langmuir adsorption isotherm. Scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), UV- Visible spectroscopy, and atomic force microscopy (AFM) were performed for a surface study of uninhibited and inhibited mild steel samples. The semi-empirical AM1 method was employed for theoretical calculations.
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Antimicrobial and anticancer activity of some novel fluorinated thiourea derivatives carrying sulfonamide moieties: synthesis, biological evaluation and molecular docking

Antimicrobial and anticancer activity of some novel fluorinated thiourea derivatives carrying sulfonamide moieties: synthesis, biological evaluation and molecular docking

The nucleophilic attack of the amino group of the aro- matic amine on thiocarbonyl group of isothiocyanate leads to formation of an intermediate (A). During the consecutive steps, deprotonation and protonation of the intermediate results in the formation of the final product thiourea. Under similar reaction conditions, treatment of isothiocyanate 2 with fluorinated heterocyclic amines such as 2-amino-2,3,5,6-tetrafluoropyridine, 2-amino- 6-fluorobenzothiazole, 2-amino-5-(trifluoromethyl)-1,3,4- thiadiazole and 7-amino-4-(trifluoromethyl)-coumarine afforded the corresponding fluorinated heterocyclic thio- ureas 4a–d, (Scheme 3). The composition and structure of products 4a–d were confirmed by the results of elemental analysis and data of IR and NMR spectra. The infrared of structure 4 displayed absorption band assignable for NH, thiocarbonyl (CS) and SO 2 groups. The infrared of 4c
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TREATMENT OF THYROTOXICOSIS IN CHILDREN WITH THIOUREA DERIVATIVES

TREATMENT OF THYROTOXICOSIS IN CHILDREN WITH THIOUREA DERIVATIVES

obvious reason. She was then given methylthiouracil, 300 mg. In spite of the large doses thyrotoxicosis persisted. Furthermore, the thyroid had increased in size. Methylthiouracil was di[r]

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Synthesis and application of thiourea S,S dioxide derivatives

Synthesis and application of thiourea S,S dioxide derivatives

When Murray’s procedure was followed, the condensation of a yellow solution of DMDO 69 in acetone was not observed. The isolation of DMDO in acetone was thought to be highly sensitive to the temperature and pressure of the generator. Numerous attempts at following Murray’s procedure, where two equivalents of DMDO were bubbled through a solution of the thiourea in dry acetone, were unsuccessful. It is known from our work that N,N’-diisopropylthiourea dioxide is insoluble in acetone. However, the precipitation of the dioxide did not occur. Instead, peroxides were detected qualitatively with iodine- starch strips and with sodium iodide/acetone/acetic acid solution in the thiourea solution flask. The thiourea flask was found to contain N,N’-diisopropylurea 47 as shown from TLC and NMR spectroscopic analyses. The scrubber had also changed into a yellow solution and, on titration with sodium thiosulfate, was found to have scrubbed two equivalents (to thiourea) of DMDO. Therefore, it was thought that a theoretical quantity of oxidant had bypassed the thiourea solution.
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