16738-18-4

Basic information

• Product Name: N-(3,4-DIMETHYLPHENYL)THIOUREA
• Synonyms: N-(3,4-DIMETHYLPHENYL)THIOUREA;AKOS BBS-00000746;(3,4-DIMETHYL-PHENYL)-THIOUREA;1-(3,4-DIMETHYLPHENYL)-2-THIOUREA
• CAS NO: 16738-18-4
• Molecular Formula: C₉H₁₂N₂S
• Molecular Weight: 180.27
• Mol File: 16738-18-4.mol

Chemical Properties

• Melting Point: 141.5-142.5 °C
• Boiling Point: 300.7°Cat760mmHg
• Flash Point: 135.7°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 0.0011mmHg at 25°C
• Refractive Index: 1.674
• PKA: 13.40±0.70(Predicted)
• CAS DataBase Reference: N-(3,4-DIMETHYLPHENYL)THIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,4-DIMETHYLPHENYL)THIOUREA(16738-18-4)
• EPA Substance Registry System: N-(3,4-DIMETHYLPHENYL)THIOUREA(16738-18-4)

Safety Data

• Hazardous Substances Data: 16738-18-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-(3,4-Dimethylphenyl)thiourea is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Dye Industry:
In the dye industry, N-(3,4-Dimethylphenyl)thiourea is used as a precursor in the production of dyes. Its ability to form stable complexes with metal ions makes it a valuable component in the creation of dyes with specific color properties and stability.
Used in Rubber Industry:
N-(3,4-Dimethylphenyl)thiourea is utilized as a rubber accelerator, enhancing the rate of vulcanization and improving the overall properties of rubber products. Its use contributes to the production of rubber with better strength, elasticity, and durability.
Used in Analytical Chemistry:
N-(3,4-Dimethylphenyl)thiourea serves as a reagent in analytical chemistry for the determination of certain metal ions. Its ability to form complexes with these metal ions allows for accurate and sensitive detection and quantification in various analytical techniques.
Used in Antidabetic Research:
N-(3,4-Dimethylphenyl)thiourea has been studied for its potential antidiabetic properties. Research is ongoing to explore its ability to modulate glucose metabolism and insulin sensitivity, which could lead to the development of new treatments for diabetes.
Used in Anti-tumor Research:
N-(3,4-DIMETHYLPHENYL)THIOUREA has also been investigated for its potential anti-tumor activities. Studies are being conducted to understand its effects on tumor growth and progression, with the aim of identifying its potential as a therapeutic agent in cancer treatment.

InChI:InChI=1/C9H12N2S/c1-6-3-4-8(5-7(6)2)11-9(10)12/h3-5H,1-2H3,(H3,10,11,12)

Upstream product

• 58655-30-4 C₆H₁₅N*C₉H₁₁NS₂ 
• 19241-17-9 3,4-xylyl isothiocyanate 
• 95-64-7 4-amino-o-xylene 
• 1147550-11-5 ammonium thiocyanate 
• 532-55-8 Benzoyl isothiocyanate 
• 117174-78-4 N-benzoyl-N'-(3,4-dimethylphenyl)thiourea 
• 333-20-0 potassium thioacyanate 
• 7356-54-9 3,4-dimethylaniline hydrochloride 

Downstream Products

• 892249-97-7 N-(3,4-dimethylphenyl)-4-(4-pyridinyl)-1,3-thiazol-2-amine 
• 70590-11-3 (3,4-dimethylphenyl)cyanamide 
• 1246780-02-8 BrH*C₁₉H₁₅ClN₄OS 
• 57478-55-4 1-acetylamino-2-acetylsulfanyl-5,4-dimethyl-benzene 
• 5683-41-0 2,5,6-trimethyl-benzothiazole 
• 119155-52-1 N-(3,4-Dimethyl-phenyl)-morpholine-4-carboxamidine; hydriodide 
• 105125-74-4 2-{3-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-propyl}-6,7-dimethyl-4H-benzo[1,4]thiazin-3-one; hydrochloride 
• 105126-18-9 2-[3-[4-(4-fluorophenyl)-1-piperazinyl]propyl]-6,7-dimethyl-2H-1,4-benzothiazin-3(4H)-one 
• 100601-29-4 2-amino-4,5-dimethylbenzenethiol 
• 119125-52-9 1-(3,4-Dimethyl-phenyl)-2-methyl-isothiourea; hydriodide 
• 29927-08-0 2-amino-5,6-dimethylbenzothiazole 
• 854057-72-0 6,7-dimethyl-benzothiazol-2-ylamine 

Relevant articles and documents

Chemical screening of novel strigolactone agonists that specifically interact with DWARF14 protein

Strigolactones (SLs) are a class of plant hormones that regulate shoot branching as well as being known as root-derived signals for parasitic and symbiotic interactions. The physical interaction between SLs and the DWARF14 (D14) receptor family can be examined by differential scanning fluorimetry (DSF) that monitors the changes in protein melting temperature (Tm). The Tm of D14 is lowered by bioactive SLs in DSF analysis. In this report, we screened the compounds that lower the Tm of Arabidopsis D14 (AtD14) as potential candidates for SL agonists using DSF analysis. Subsequent physiological analyzes revealed that 113D10 acts as a novel SL agonist in a D14-dependent manner. Intriguingly, 113D10 has a chemical structure different from natural SLs in that it does not possess an enol ether bond that connects to a methylbutenolide moiety. Moreover, 113D10 does not stimulate seed germination of root parasitic plants. Accordingly, 113D10 can be a useful tool for SL studies and agricultural applications.

Effect of N-1 arylation of monastrol on kinesin Eg5 inhibition in glioma cell lines

An original and focused library of two sets of dihydropyrimidin-2-thiones (DHPMs) substituted with N-1 aryl groups derived from monastrol was designed and synthesized in order to discover a more effective Eg5 ligand than the template. Based on molecular docking studies, four ligands were selected to perform pharmacological investigations against two glioma cell lines. The results led to the discovery of two original compounds, called 20h and 20e, with an anti-proliferative effects, achieving IC50 values of about half that of the IC50 of monastrol in both cell lines. As with monastrol, flow cytometry analyses showed that the 20e and 20h compounds induced cell cycle arrest in the G2/M phase, and immunocytochemistry essays revealed the formation of monopolar spindles due to Eg5 inhibition without any toxicity to Caenorhabditis elegans.

Synthesis and bioevaluation of N,4-diaryl-1,3-thiazole-2-amines as tubulin inhibitors with potent antiproliferative activity

A series of N,4-diaryl-1,3-thiazole-2-amines containing three aromatic rings with an amino linker were designed and synthesized as tubulin inhibitors and evaluated for their antiproliferative activity in three human cancer cell lines. Most of the target compounds displayed moderate antiproliferative activity, and N-(2,4-dimethoxyphenyl)-4-(4-methoxyphenyl)-1,3-thiazol-2-amine (10s) was determined to be the most potent compound. Tubulin polymerization and immunostaining experiments revealed that 10s potently inhibited tubulin polymerization and disrupted tubulin microtubule dynamics in a manner similar to CA-4. Moreover, 10s effectively induced SGC-7901 cell cycle arrest at the G2/M phase in both concentrationand time-dependent manners. The molecular docking results revealed that 10s could bind to the colchicine binding site of tubulin.

Synthesis of monosubstituted thioureas by vapour digestion and mechanochemical amination of thiocarbamoyl benzotriazoles

Thiocarbamoyl benzotriazoles, as safe and easy-to-handle isothiocyanate equivalents, were quantitatively converted to N-monosubstituted thioureas by vapour digestion synthesis under an ammonia atmosphere. This simple, but timely process provided a synthetic platform that enabled the "slow" amination reaction to be successfully transformed into a rapid one aided by mechanochemical milling. The ammonium chloride/sodium carbonate equimolar mixture allowed in situ formation of ammonia under ball-milling conditions. This novel and green approach yielded aromatic and aliphatic primary thioureas in near-quantitative isolated yields with workup entirely based on using only water. In addition, the molecular and crystal structures of selected polyaromatic primary thioureas were determined from the synchrotron powder diffraction data.

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.

Design, synthesis, X-ray crystallographic analysis, and biological evaluation of thiazole derivatives as potent and selective inhibitors of human dihydroorotate dehydrogenase

Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.

Synthesis and Cytotoxicity in Vitro of N-Aryl-4-(Tert-butyl)-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine

A series of novel N-aryl-4-(tert-butyl)-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amines were synthesized in a green way. H2O2-NaBr Brominating circulatory system was used in the synthesis of the key intermediate in a mild condition. All of the target compounds were confirmed by1H NMR and elemental analysis and tested for their cytotoxicity against two different human cancer cell lines. The cytotoxicity assay revealed that some of the title compounds showed moderate to strong cytotoxic activities. Compound 2i was the most potent compound with the IC50 values of 9 μMagainst Hela cells and 15 μMagainst Bel-7402 cells, respectively.

Environmentally benign one-pot synthesis of cyanamides from dithiocarbamates using I2 and H2O2

An environmentally benign reaction is devised for the synthesis of cyanamides from dithiocarbamate salts using iodine and H2O 2. Taylor & Francis Group, LLC.

4-Pyridylanilinothiazoles that selectively target von Hippel - Lindau deficient renal cell carcinoma cells by inducing autophagic cell death

Renal cell carcinomas (RCC) are refractory to standard therapy with advanced RCC having a poor prognosis; consequently treatment of advanced RCC represents an unmet clinical need. The von Hippel-Lindau (VHL) tumor suppressor gene is mutated or inactivated in a majority of RCCs. We recently identified a 4-pyridyl-2-anilinothiazole (PAT) with selective cytotoxicity against VHL-deficient renal cells mediated by induction of autophagy and increased acidification of autolysosomes. We report exploration of structure-activity relationships (SAR) around this PAT lead. Analogues with substituents on each of the three rings, and various linkers between rings, were synthesized and tested in vitro using paired RCC4 cell lines. A contour map describing the relative spatial contributions of different chemical features to potency illustrates a region, adjacent to the pyridyl ring, with potential for further development. Examples probing this domain validated this approach and may provide the opportunity to develop this novel chemotype as a targeted approach to the treatment of RCC. 2009 American Chemical Society.

HETEROARYL COMPOUNDS, COMPOSITIONS, AND METHODS OF USE IN CANCER TREATMENT

Provided herein are novel heteroaryl compounds, compositions comprising the compounds, and methods of treatment or prevention comprising administration of the compounds. The compounds are effective in the targeting of cells defective in the von Hippel-Lindau gene and in inducing autophagic cell death. The methods are directed to treating or preventing diseases such as cancer, and in particular cancers resulting from von Hippel-Lindau disease. The compounds of the invention may be administered in combination with another therapeutic agent.