2103-91-5

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-4-(P-TOLYL)THIAZOLE is used as a building block for the synthesis of various pharmaceuticals and drug compounds. Its unique structure allows it to be a key component in the development of new medications, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Production:
In the agrochemical sector, 2-AMINO-4-(P-TOLYL)THIAZOLE is utilized in the production of various agrochemicals. Its properties make it suitable for the creation of compounds that can be used in agricultural applications to protect crops and enhance yields.
Used as an Intermediate in Organic Synthesis:
2-AMINO-4-(P-TOLYL)THIAZOLE also serves as an intermediate in organic synthesis. Its reactivity and structural features make it a valuable precursor in the synthesis of a range of organic compounds, expanding its applications beyond the pharmaceutical and agrochemical realms.
Used in Medicinal Chemistry and Drug Discovery:
Due to its distinctive structure and properties, 2-AMINO-4-(P-TOLYL)THIAZOLE has potential applications in medicinal chemistry and drug discovery. Researchers can leverage its chemical characteristics to explore new avenues in the development of therapeutic agents and pharmaceutical interventions.

InChI:InChI=1/C10H10N2S/c1-7-2-4-8(5-3-7)9-6-13-10(11)12-9/h2-6H,1H3,(H2,11,12)

Upstream product

• 17356-08-0 thiourea 
• 122-00-9 para-methylacetophenone 
• 619-41-0 4-(bromoacetyl)toluene 
• 98475-04-8 1-(4-methylphenyl)-2-(p-tolylsulfonyloxy)ethanone 
• 17263-64-8 2-diazo-1-(4-methylphenyl)ethanone 
• 40805-62-7 2-iodo-1-(4-methylphenyl)ethanone 
• 13664-98-7 2,2-dibromo-1-(4-methylphenyl)ethanone 
• 766-97-2 4-n-methylphenylacetylene 
• 333-20-0 potassium thioacyanate 
• 89108-49-6 1-(1-azidovinyl)-4-methyl benzene 
• 874-60-2 4-methyl-benzoyl chloride 
• 100-19-6 (4-nitrophenyl)ethanone 
• 1147550-11-5 ammonium thiocyanate 
• 4209-24-9 p-methylphenacyl chloride 

Downstream Products

• 450-41-9 4-fluoro-benzenesulfonic acid-(4-p-tolyl-thiazol-2-ylamide) 
• 99973-40-7 4-(4-methylphenyl)-5-thiocyanato-2-aminothiazole 
• 103158-34-5 4,4'-di-p-tolyl-5,5'-benzylidene-bis-thiazol-2-ylamine 
• 109067-38-1 N-acetyl-sulfanilic acid-(4-p-tolyl-thiazol-2-ylamide) 
• 39564-97-1 3-p-tolyl-pyrido[2,3-d]thiazolo[3,2-a]pyrimidin-5-one 
• 2211-40-7 (1H-benzoimidazol-2-ylmethyl)-(4-p-tolyl-thiazol-2-yl)-amine 
• 74636-85-4 2-methyl-3-(4-p-tolyl-thiazol-2-yl)-3H-quinazolin-4-one 
• 92498-86-7 5-nitro-furan-2-carboxylic acid 4-p-tolyl-thiazol-2-ylamide 
• 69396-07-2 N-[(4-p-tolyl-thiazol-2-ylamino)-methyl]-phthalimide 
• 72307-67-6 acridin-9-yl-(4-p-tolyl-thiazol-2-yl)-amine 
• 79652-52-1 7-[Phenyl-(4-p-tolyl-thiazol-2-ylamino)-methyl]-quinolin-8-ol 
• 111249-33-3 N-<4-(4'-methylphenyl)thiazol-2-yl>thiosemicarbazide 
• 77203-57-7 2,4-Dibromo-6-{[(E)-4-p-tolyl-thiazol-2-ylimino]-methyl}-phenol 
• 100003-86-9 7-chloromethyl-3-(4-methylphenyl)-5H-thiazolo<3,2-a>pyrimidine-5-one 

Relevant academic research and scientific papers

1-Methylimidazolium ionic liquid supported on Ni@zeolite-Y: fabrication and performance as a novel multi-functional nanocatalyst for one-pot synthesis of 2-aminothiazoles and 2-aryl benzimidazoles

In the present study, 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride-supported Ni@zeolite-Y-based nanoporous materials (Ni@zeolite-Im-IL) were synthesized and their structures were confirmed using different characterization techniques such as FT-IR, FE-SEM, EDX, XRD, BET and TGA-DTG analyses. In order to synthesize this multi-functional nano-system, zeolite-NaY was modified first, with exchanged Ni2+ ions and 3-chloropropyltriethoxysilane (CPTES) as a coupling reagent and then functionalized to imidazolium chloride ionic liquid by N-methylimidazole. New multi-functional nano-material of Ni@zeolite-Im-IL demonstrated high activity in the catalytic synthesis of 2-aminothiazoles 3a–l by one-pot reaction of methylcarbonyls, thiourea and iodine at 80?°C in DMSO with good to excellent yields (85–98%). Also, the catalytic synthesis of 2-aryl benzimidazoles, 6a–m was performed by the condensational reaction of o-arylendiamine and aromatic aldehydes in EtOH at room temperature with excellent yields (90–98%). Advantages of this efficient synthetic strategy include higher purity and shorter reaction time, excellent yield, easy isolation of products, the good stability, activity and feasible reusability of the metallic ionic liquid nanocatalyst. These benefits have made this method more compatible with the principles of green chemistry. Graphical abstract: [Figure not available: see fulltext.]

Novel 4-(piperazin-1-yl)quinolin-2(1H)-one bearing thiazoles with antiproliferative activity through VEGFR-2-TK inhibition

A new series of 2-(4-(2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide derivatives were synthesized and evaluated for anticancer activity. All target compounds showed anticancer activity higher than that of their 2-oxo-4-piperazinyl-1,2-dihydroquinolin-2(1H)-one precursors. Multidose testing of target compounds was performed against breast cancer T-47D cell line. Five compounds showed higher cytotoxic activity than Staurosporine. The dihalogenated derivative showed the best cytotoxic activity with IC50 2.73 ± 0.16 μM. In addition, the VEGFR-2 inhibitory activity of all synthetic compounds was evaluated. Two compounds of 6-fluoro-4-(piperazin-1-yl)quinolin-2(1H)-ones showed inhibitory activity comparable to sorafenib with IC50 46.83 ± 2.4, 51.09 ± 2.6 and 51.41 ± 2.3 nM, respectively. The cell cycle analysis of two compounds namely, 2-(4-(6-fluoro-2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide and N-(4-(4-chlorophenyl)thiazol-2-yl)-2-(4-(2-oxo-1-phenyl-1,2-dihydroquinolin-4-yl)piperazin-1-yl)acetamide revealed that the arrest of cell cycle occurred at S phase. In apoptosis assay, the same two compounds were able to induce significant levels of early and late apoptosis. In a similar manner to Sorafenib, docking of target compounds with VEGFR-2 protein 4ASD showed HB with Cys919 in hinge region of enzyme and HB with both Glu885 and Asp1046 in gate area. Using SwissADME, all target compounds were predicted to be highly absorbed from gastrointestinal tract with no BBB permeability. It is clear that the two compounds are promising antiproliferative candidates that require further optimization.

Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors

A novel series of phenoxymethybenzoimidazole derivatives (9a-n) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC50 values in the range of 6.31 to 49.89?μM compared to standard drug acarbose (IC50 = 750.0 ± 10.0?μM). Enzyme kinetic studies on 9c, 9g, and 9m as the most potent compounds revealed that these compounds were uncompetitive inhibitors into α-glycosidase. Docking studies confirmed the important role of benzoimidazole and triazole rings of the synthesized compounds to fit properly into the α-glycosidase active site. This study showed that this scaffold can be considered as a highly potent α-glycosidase inhibitor.

Synthesis, characterization and evaluation of new thiazole derivatives as anthelmintic agents

A series of 2-amino substituted 4-phenyl thiazole derivatives has been synthesized by the conventional method. The thiazole derivatives have been synthesized by three steps. The obtained five derivatives have been purified by recrystallization process by using methanol as solvent and column chromatography [IVd Compound] and have been characterized by melting point, TLC, FTIR, 1H NMR and mass spectral data. All the five derivatives have been evaluated using in silico studies by using different softwares (Lipinski's Rule of 5, OSIRIS molecular property explorer, Molsoft molecular property explorer, PASS and docking studies). These compounds have then been evaluated for anthelmintic activity against Indian adult earth worms (Pheretima postuma). All the compounds show significant anthelmintic activity. The compound IVc and IVe are shown to be potent compounds when compared with the standard drug (Mebendazole). Molecular docking studies have guided and prove the biological activity of the sythesised compounds against beta tubulin protein (1OJ0).

Solid state thiazole-based fluorophores: Promising materials for white organic light emitting devices

A facile and more efficient solvent-free mechanochemical synthetic route has been developed for the synthesis of a series of solid state white light emissive thiazole-based donor-acceptor (D-A) type fluorophores, 2-(3-pyridyl)/2-aminothiazoles from ω-bromomethylketones and pyridine-3-carbothioamide/thiourea in the presence of silica-supported HClO4 as a reusable solid Br?nsted acid catalyst at RT. The photophysical and electrochemical properties of these compounds have been derived. Most of the studied D-A type solid thiazole-based fluorophores emitted white light and it can be tuned from warm - ideal - cold white light by introduction of a variety of substituents at 4th position of 2-(3-pyridyl)/2-aminothiazoles. Further, HOMO and LUMO energy levels of the titled compounds are found to be in the range ?5.52 eV to ?5.72 eV and ?1.84 eV to ?2.45 eV, respectively. The lifetimes of these levels of thiazole-based fluorophores have been determined through luminescence decay curves and are found to be in the range of 7.7–11 μs. The photophysical and electrochemical properties of the synthesized thiazole-based fluorophores indicate that the compounds could be promising materials for white organic light emitting devices.

Gramine-based structure optimization to enhance anti-gastric cancer activity

Gramine is a natural indole alkaloid with a wide range of biological activities, but its anti-gastric cancer activity is poor. Herein, a pharmacophore fusion strategy was adopted to design and synthesize a new series of indole-azole hybrids on the structural basis of gramine. Based on our previous studies, different nitrogen-containing five-membered heterocyclic rings and terminal alkyne group were introduced into the indole-based scaffold to investigate their effect on improving the anti-gastric cancer activity of gramine derivatives. Structure-activity relationship (SAR) studies highlighted the role played by terminal alkyne in enhancing the inhibitory effect, and compound 16h displayed the best antiproliferative activity against gastric cancer MGC803 cells with IC50 value of 3.74 μM. Further investigations displayed compound 16h could induce mitochondria-mediated apoptosis, and caused cell cycle arrest at G2/M phase. Besides, compound 16h could inhibit the metastasis ability of MGC803 cells. Our studies may provide a new strategy for structural optimization of gramine to enhance anti-gastric cancer activity, and provide a potential candidate for the treatment of gastric cancer.

Molecular properties prediction, synthesis, and antimicrobial activity of bis(azolyl)sulfonamidoacetamides

A library of bis(azolyl)sulfonamidoacetamides was prepared by the reaction of azolylsulfonylamines with azolylchloroacetamides in the presence of pyridine/4-(dimethylamino)pyridine (DMAP) under ultrasonication. The reaction proceeded well with DMAP, resulting in a higher yield of the products. The antimicrobial activity of the compounds indicated that N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl)amino}-2-oxoethyl)sulfamoyl]-4-phenylthiazol-2-yl}benzamide (22a), N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl]amino}-2-oxoethyl)sulfamoyl]-4-(4-chlorophenyl)thiazol-2-yl}benzamide (22c), and N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl]amino}-2-oxoethyl)sulfamoyl]-4-(4-chloro-phenyl)-1H-imidazol-2-yl}benzamide (24c) exhibited a low minimal inhibitory concentration (MIC) against Bacillus subtilis, equal to the standard drug, chloramphenicol. Compounds 22c and 24c also showed low MICs against Aspergillus niger, equal to the standard drug, ketoconazole. The molecular properties of the synthesized molecules were studied to identify druglikeness properties of the target compounds. On the basis of molecular properties prediction, 19a, 19b, 20b, 20c, 21a–c, 22b, 22c, and 23a–c can be treated as drug candidates.

Synthesis of 6-membered-ring fused thiazine-dicarboxylates and thiazole-pyrimidines via one-pot three-component reactions

A facile and efficient one-pot three-component reaction method for the synthesis of thiazine-dicarboxylates is reported. Reaction of an isocyanide and dialkyl acetylenedicarboxylate with 2-amino-4H-1,3-thiazin-4-one derivatives containing both an acidic proton and an internal nucleophile gave the products in good yields of 76–85%. The reactivity of dialkyl acetylenedicarboxylates was further tested in the synthesis of thiazole-pyrimidines where a two-component reaction of 2-aminothiazole with dialkyl acetylenedicarboxylates was successfully converted to a more efficient three-component reaction of a thiourea, α-haloketone and dialkyl acetylenedicarboxylate (DMAD/DEtAD) to give thiazole-pyrimidines in good yields of 70–91%.

Aiding the versatility of simple ammonium ionic liquids by the synthesis of bioactive 1,2,3,4-tetrahydropyrimidine, 2-aminothiazole and quinazolinone derivatives

Simple ammonium ionic liquids [ILs] are efficient, green, environmentally friendly catalysts in promoting the Biginelli condensation reaction, Hantzsch reaction and Niementowski reaction to afford 1,2,3,4-tetrahydropyrimidine, 2-aminothiazole and quinazolinone derivatives respectively by eliminating the need for harmful volatile organic solvents. These [ILs] are air and water stable, easy to prepare and cost-effective. The effects of the anions and cations present in [IL] on reactions were investigated. The results clearly indicated that the Biginelli condensation reaction, Hantzsch reaction and Niementowski reaction were heavily influenced by the acidity of [IL], and among various ammonium ionic liquids, [Et3NH][HSO4] showed the best catalytic activity. Furthermore, [IL] could be easily separated and reused with a slight loss of its activity. This technique provided a good alternative way for the industrial synthesis of 1,2,3,4-tetrahydropyrimidinones, 2-aminothiazoles and quinazolinones. The present processes are eco-friendly methods for the synthesis of these derivatives authenticated by several green parameters, namely,E-factor, process mass intensity, reaction mass efficiency, atom economy, and carbon efficiency.

A one-pot synthesis of 2-aminothiazoles via the coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system

A series of 2-aminothiazoles is prepared in moderate-to-good yields by the direct coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system. This method avoids the preparation of lachrymatory and toxic α-haloketones and the use of an acid-binding agent, thus providing a more convenient approach to 2-aminothiazoles compared to the Hantzsch reaction.