621-40-9

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-METHYLPHENYL)-2-THIOUREA is used as a pharmaceutical intermediate for its potential antitumor and antifungal activities. Its unique chemical structure allows it to interact with biological targets, making it a promising candidate for the development of new drugs to combat cancer and fungal infections.
Used in Organic Synthesis:
1-(3-METHYLPHENYL)-2-THIOUREA is used as a building block in the synthesis of various organic compounds. Its versatile chemical properties enable it to participate in a range of reactions, contributing to the formation of complex organic molecules with diverse applications.
Used as a Reagent in Chemical Reactions:
In the field of chemistry, 1-(3-METHYLPHENYL)-2-THIOUREA is employed as a reagent to facilitate specific chemical transformations. Its ability to participate in reactions such as condensation, substitution, and rearrangement makes it a valuable tool for chemists in their pursuit of novel compounds and materials.
Overall, 1-(3-METHYLPHENYL)-2-THIOUREA's diverse applications across different industries highlight its significance as a versatile chemical compound with potential for further exploration and development in various scientific and industrial fields.

InChI:InChI=1/C8H10N2S/c1-6-3-2-4-7(5-6)10-8(9)11/h2-5H,1H3,(H3,9,10,11)

Upstream product

• 333-20-0 potassium thioacyanate 
• 108-44-1 1-amino-3-methylbenzene 
• 621-30-7 3-methylphenyl isothiocyanate 
• 4949-87-5 N-benzoyl-N′-(3-methylphenyl)thiourea 
• 60-29-7 diethyl ether 
• 7664-41-7 ammonia 
• 620-51-9 N,N'-di(3-methylphenyl)thiourea 
• 540-72-7 sodium thiocyanide 
• 1147550-11-5 ammonium thiocyanate 
• 638-03-9 m-toluidine hydrochloride 
• 17356-08-0 thiourea 

Downstream Products

• 14779-17-0 2-amino-5-methylbenzothiazole 
• 14779-18-1 7-methyl-1,3-benzothiazol-2-amine 
• 55591-33-8 3-methylphenylcyanamide 
• 27052-16-0 2-(3-tolylimino)-1,3-thiazol-4-one 
• 37394-96-0 m-tolylcarbamimidoylmercapto-acetic acid 
• 61108-40-5 (4'-methyl-2'-phenyl-[4,5']bithiazolyl-2-yl)-m-tolyl-amine 
• 61108-54-1 [2'-(4-chloro-phenyl)-4'-methyl-[4,5']bithiazolyl-2-yl]-m-tolyl-amine 
• 104510-10-3 5-ethyl-2-(3-methyl-anilino)-thiazol-4-one 
• 23993-30-8 4-amino-2-imino-3-m-tolyl-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 21017-99-2 [4-methyl-2-(3-methyl-anilino)-thiazol-5-yl]-acetic acid ethyl ester 
• 108667-96-5 5-benzyl-2-(3-methyl-anilino)-thiazol-4-one 
• 95942-28-2 4-amino-5-phenyl-3-m-tolyl-3H-thiazol-2-ylideneamine 
• 27052-16-0 2-(3-methyl-anilino)-thiazol-4-one 
• 18792-27-3 5-methyl-2-(3-methyl-anilino)-thiazol-4-one 

Relevant academic research and scientific papers

Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea

An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.

Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles

[Figure not available: see fulltext.] The synthesis of cyanamides and tetrazoles from isothiocyanates through tandem reaction using cobalt catalyst has been demonstrated. In the case of tetrazole preparation, the reaction involved addition/desulfurization/nucleophilic addition/electrocyclization, whereas aromatic cyanamides were constructed from isothiocyanates through addition/desulfurization. Cheap cobalt sulfate was used for the synthesis of various cyanamides and tetrazoles. In addition, cobalt catalyst was found to be desulfurization reagent that has not been previously reported. The final products have been obtained from starting precursors in good to high yield.

Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against: Klebsiella pneumoniae

A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712). Some of the synthesized compounds exhibited synergistic activity. When 4 μg ml-1 compound B1 was combined with PB, it showed potent antibacterial activity, achieving 64-fold reduction of the MIC of PB. Furthermore, compound B1 showed prominent synergistic efficacy in both concentration gradient and time-kill curves in vitro. In addition, B1 combined with PB also exhibited synergistic and partial synergistic effect against E. coli (ATCC25922 and its clinical isolates), Acinetobacter baumannii (ATCC19606 and its clinical isolates), and Pseudomonas aeruginosa (Pae-1399).

Synthesis and antitumor evaluation of 5-(benzo[: D] [1,3]dioxol-5-ylmethyl)-4-(tert -butyl)- N -arylthiazol-2-amines

A series of novel N-aryl-5-(benzo[d][1,3]dioxol-5-ylmethyl)-4-(tert-butyl)thiazol-2-amines (C1-C31) were synthesized and evaluated for their antitumor activities against HeLa, A549 and MCF-7 cell lines. Some tested compounds showed potent growth inhibition properties with IC50 values generally below 5 μM against the three human cancer cells lines. Compound C27 showed potent activities against HeLa and A549 cell lines with IC50 values of 2.07 ± 0.88 μM and 3.52 ± 0.49 μM, respectively. Compound C7 (IC50 = 2.06 ± 0.09 μM) was the most active compound against A549 cell line, while compound C16 (IC50 = 2.55 ± 0.34 μM) showed the best inhibitory activity against the MCF-7 cell line. The preliminary mechanism of the inhibitory effect was investigated via further experiments, such as morphological analysis by dual AO/EB staining and Hoechst 33342 staining, and cell apoptosis and cycle assessment by FACS analysis. The results illustrated that compound C27 could induce apoptosis and cause both S-phase and G2/M-phase arrests in HeLa cell line. Therefore, compound C27 could be developed as a potential antitumor agent.

A thiazolidine compound of ketones, and its preparation for treating iron disorder related disease application of the medicament (by machine translation)

The invention discloses a thiazolidone compound, wherein a chemical structure of the thiazolidone compound is shown in a general form (I). The invention also discloses application of the thiazolidone compound in preparation of a medicine used for treating thalassemia. Experiments prove that the thiazolidone compound can be used for effectively stimulating expression of hepcidin in cells under the condition that concentration is 10mu M, can be still used for effectively inducing expression of hepcidin in liver when being exposed for 6 hours, 24 hours and 48 hours respectively at a dosage of 30mg/kg in animal level and can be also used for effectively reducing level of serum iron, so that the thiazolidone compound can take hepcidin as a target, can be used for reducing iron level in serum, is hopeful to be a potential medicine used for treating and alleviating iron disorder-related diseases and has a broad clinical application prospect and a great economic development value.

Probing the ATP-Binding Pocket of Protein Kinase DYRK1A with Benzothiazole Fragment Molecules

DYRK1A has emerged as a potential target for therapies of Alzheimer's disease using small molecules. On the basis of the observation of selective DYRK1A inhibition by firefly d-luciferin, we have explored static and dynamic structural properties of fragment sized variants of the benzothiazole scaffold with respect to DYRK1A using X-ray crystallography and NMR techniques. The compounds have excellent ligand efficiencies and show a remarkable diversity of binding modes in dynamic equilibrium. Binding geometries are determined in part by interactions often considered "weak", including "orthogonal multipolar" types represented by, for example, F-CO, sulfur-aromatic, and halogen-aromatic interactions, together with hydrogen bonds that are modulated by variation of electron withdrawing groups. These studies show how the benzothiazole scaffold is highly promising for the development of therapeutic DYRK1A inhibitors. In addition, the subtleties of the binding interactions, including dynamics, show how full structural studies are required to fully interpret the essential physical determinants of binding.

C-S bond-forming reactions of barbiturylbromide with isothiocarbamides in aqueous media

The C-S cross coupling of pharmaceutically active barbituric acid derivatives has been achieved by the interaction of selective monobromobarbituric acid with thioureas in an aqueous medium. This method is applicable for simple thiourea as well as monosubstituted thioureas, and corresponding products are obtained in good yield. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Design, synthesis and investigation on the structure-activity relationships of N-substituted 2-aminothiazole derivatives as antitubercular agents

Tuberculosis (TB) is one of the deadliest infectious diseases of all times, and its recent resurgence is a supreme matter of concern. Co-infection with HIV and, in particular, the continuous isolation of new resistant strains, makes the discovery of novel anti-TB agents a strategic priority. The research of novel agents should be driven by the accessibility of the synthetic procedure and, in particular, by the lack of cross-resistance with the drugs already marketed. Moreover, in order to shorten the duration of the therapy, and therefore decrease the rate of resistance, these molecules should be active also against the nonreplicating persistent form (NRP-TB) of the infection. The availability of an in-house small library of compounds prompted us to investigate their anti-TB activity. Two compounds, embodying a 2-aminothiazole scaffold, were found to possess a certain inhibitory activity toward Mycobacterium tuberculosis H37Rv, and therefore a medicinal chemistry campaign was initiated in order to increase the activity of the hit compounds and, especially, construct a plausible body of structure-activity relationships. The potency of the hit compound was successfully improved, and, much more importantly, some of the molecules synthesized were found to be active toward the persistent phenotype, and, also, toward a panel of resistant strains. These findings encourage further investigations around this interesting antitubercular chemotype.

Structure-activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis

A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl) -1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 μM or 0.008 μg/mL in 7H9 media and therapeutic index of nearly ～300. However, 55 is rapidly metabolized by human liver microsomes (t1/2 = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of ～10-5.

Design and synthesis of N-Aryl isothioureas as a novel class of gastric H+/K+-ATPase inhibitors

To find new H+/K+-ATPase inhibitors for the treatment of peptic ulcer disease, a series of novel N-aryl isothiourea derivatives were synthesized and their structures were identified by 1H NMR and GC-MS. The effects of these compounds on inhibiting gastric acid secretion were evaluated by the guinea pig stomach mucous membrane study with pantoprazole magnesium as a positive control. The results showed that, of the 37 N-aryl isothiourea compounds synthesized, 20 compounds have comparable or stronger gastric acid inhibitory activities than that of pantoprazole magnesium. The quantitative structure-activity relationships (QSARs) of the N-aryl isothiourea compounds were also studied by comparative molecular field analysis (CoMFA) computation, and the model structure that was supposed to give more powerful bioactivities was finally predicted. A series of novel N-aryl isothiourea derivatives were synthesized and evaluated for their effects of inhibiting gastric acid secretion using the guinea pig stomach mucous membrane study with pantoprazole magnesium as a positive control. Compounds 2c, 2e, and 2k have higher bioactivity. The quantitative structure-activity relationships also defined these structural requirements.