6396-76-5

Basic information

• Product Name: 1-(2,6-DIMETHYLPHENYL)-2-THIOUREA
• Synonyms: 1-(2,6-DIMETHYLPHENYL)-2-THIOUREA;2,6-DIMETHYLPHENYLTHIOUREA;N-(2,6-DIMETHYLPHENYL)THIOUREA;1-(2,6-xylyl)thiourea;1-(2,6-Xylyl)-2-Thiourea
• CAS NO: 6396-76-5
• Molecular Formula: C₉H₁₂N₂S
• Molecular Weight: 180.27
• EINECS: 229-005-8
• Mol File: 6396-76-5.mol

Chemical Properties

• Melting Point: 195 °C
• Boiling Point: 284.4 °C at 760 mmHg
• Flash Point: 125.8 °C
• Appearance: /
• Density: 1.2 g/cm³
• Vapor Pressure: 0.00298mmHg at 25°C
• Refractive Index: 1.674
• PKA: 13.15±0.70(Predicted)
• BRN: 2209836
• CAS DataBase Reference: 1-(2,6-DIMETHYLPHENYL)-2-THIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,6-DIMETHYLPHENYL)-2-THIOUREA(6396-76-5)
• EPA Substance Registry System: 1-(2,6-DIMETHYLPHENYL)-2-THIOUREA(6396-76-5)

Safety Data

• Statements: 25
• Safety Statements: 22-36/37-45
• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 6396-76-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Reactions:
1-(2,6-DIMETHYLPHENYL)-2-THIOUREA is used as a hydrogen peroxide scavenger to neutralize hydrogen peroxide in various chemical processes, thereby preventing unwanted side reactions and ensuring the desired reaction proceeds efficiently.
Used in Medical and Pharmaceutical Industries:
1-(2,6-DIMETHYLPHENYL)-2-THIOUREA is used as an antioxidant and protective agent against oxidative stress, leveraging its potential to mitigate the harmful effects of reactive oxygen species in biological systems.
Used in Anticancer Research:
1-(2,6-DIMETHYLPHENYL)-2-THIOUREA is used in the study of its effects on inhibiting the growth of certain types of cancer cells, exploring its potential as a therapeutic agent in oncology.
Used in Safety Protocols:
1-(2,6-DIMETHYLPHENYL)-2-THIOUREA is used with caution in laboratory and industrial settings, as it may cause skin and eye irritation, requiring the use of proper protective equipment and ensuring that it is handled in well-ventilated areas.

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

Upstream product

• 6544-02-1 silicon tetraisothiocyanate 
• 87-62-7 2,6-dimethylaniline 
• 1147550-11-5 ammonium thiocyanate 
• 19241-16-8 2,6-dimethylphenylisothiocyanate 
• 87544-32-9 [3-Benzoyl-1-(2,6-dimethyl-phenyl)-thioureido]-acetic acid tert-butyl ester 
• 540-72-7 sodium thiocyanide 
• 25343-24-2 N-((2,6-dimethylphenyl)carbamothioyl)benzamide 
• 119072-54-7 2,6-dimethylphenyl isonitrile 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 

Downstream Products

• 54708-12-2 (2,6-dimethyl-phenyl)-thiazol-2-yl-amine 
• 27806-86-6 1-(2,6-Dimethyl-phenyl)-2-methyl-isothiourea; hydriodide 
• 159615-60-8 4,6-Diamino-1-(2,6-dimethyl-phenyl)-1H-pyrimidine-2-thione 
• 1187669-29-9 N-(2,6-dimethylphenyl)-4-(4-pyridinyl)-1,3-thiazol-2-amine 
• 27806-79-7 methyl N'-(2,6-dimethylphenyl)carbamimidothioate 
• 124111-95-1 C₉H₁₄N₄ 
• 1392735-23-7 (Z)-3-amino-2-(2,6-dimethylphenylimino)thiazolidin-4-one 
• 1392724-38-7 (Z)-2-(2,6-dimethylphenylimino)-3-((E)-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylideneamino)thiazolidin-4-one 
• 65070-10-2 N-(2,6-Dimethyl-phenyl)-pyrrolidine-1-carboxamidine; hydriodide 

Relevant articles and documents

Chromatography-Free Multicomponent Synthesis of Thioureas Enabled by Aqueous Solution of Elemental Sulfur

The development of a new three-component chromatography-free reaction of isocyanides, amines and elemental sulfur allowed us the straightforward synthesis of thioureas in water. Considering a large pool of organic and inorganic bases, we first optimized the preparation of aqueous polysulfide solution from elemental sulfur. Using polysulfide solution, we were able to omit the otherwise mandatory chromatography, and to isolate the crystalline products directly from the reaction mixture by a simple filtration, retaining the sulfur in the solution phase. A wide range of thioureas synthesized in this way confirmed the reasonable substrate and functional group tolerance of our protocol.

Convenient Multicomponent One-Pot Synthesis of 2-Iminothiazolines and 2-Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions

Herein, we present a novel one-pot aqueous reaction for the synthesis of 2-iminothiazolines and 2-aminothiazoles using isocyanides, amines, sulfur, and 2′-bromoacetophenones. The three-component preparation of thioureas is followed by the one-pot cyclization leading to the heterocyclic product. This efficient and mild procedure features excellent step- and atom-economy and enables the chromatography-free preparation of diversely substituted 2-iminothiazoline and 2-aminothiazole derivatives.

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.

A COLORANT COMPOUND, AND A COLORANT MATERIAL COMPRISING THE SAME

A disclosure of the present invention includes novel colorant compounds based on triarylmethane structure, methods for preparing the same, and colorant materials comprising the same.

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 poised fragment library enables rapid synthetic expansion yielding the first reported inhibitors of PHIP(2), an atypical bromodomain

Research into the chemical biology of bromodomains has been driven by the development of acetyl-lysine mimetics. The ligands are typically anchored by binding to a highly conserved asparagine residue. Atypical bromodomains, for which the asparagine is mutated, have thus far proven elusive targets, including PHIP(2) whose parent protein, PHIP, has been linked to disease progression in diabetes and cancers. The PHIP(2) binding site contains a threonine in place of asparagine, and solution screening have yielded no convincing hits. We have overcome this hurdle by combining the sensitivity of X-ray crystallography, used as the primary fragment screen, with a strategy for rapid follow-up synthesis using a chemically-poised fragment library, which allows hits to be readily modified by parallel chemistry both peripherally and in the core. Our approach yielded the first reported hit compounds of PHIP(2) with measurable IC50 values by an AlphaScreen competition assay. The follow-up libraries of four poised fragment hits improved potency into the sub-mM range while showing good ligand efficiency and detailed structural data.

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.

Structure-activity relationship of semicarbazone EGA furnishes photoaffinity inhibitors of anthrax toxin cellular entry

EGA, 1, prevents the entry of multiple viruses and bacterial toxins into mammalian cells by inhibiting vesicular trafficking. The cellular target of 1 is unknown, and a structure-activity relationship study was conducted in order to develop a strategy for target identification. A compound with midnanomolar potency was identified (2), and three photoaffinity labels were synthesized (3-5). For this series, the expected photochemistry of the phenyl azide moiety is a more important factor than the IC50 of the photoprobe in obtaining a successful photolabeling event. While 3 was the most effective reversible inhibitor of the series, it provided no protection to cells against anthrax lethal toxin (LT) following UV irradiation. Conversely, 5, which possessed weak bioactivity in the standard assay, conferred robust irreversible protection vs LT to cells upon UV photolysis.

PROTECTIVE MOLECULES AGAINST ANTHRAX TOXIN

Disclosed herein inter alia are compositions and methods useful in the treatment of infectious diseases and exposure to toxins.

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.