57493-24-0

Usage

Uses

Used in Pharmaceutical Industry:
4-(3-Nitro-phenyl)-thiazol-2-ylamine is used as a building block for the synthesis of biologically active compounds due to its unique structural features and potential to impart specific properties to the resulting molecules.
Used in Antimicrobial Applications:
4-(3-Nitro-phenyl)-thiazol-2-ylamine is used as an intermediate in the development of antimicrobial agents, as thiazole derivatives have been studied for their potential in this area.
Used in Antiviral Applications:
4-(3-Nitro-phenyl)-thiazol-2-ylamine is used as an intermediate in the development of antiviral agents, given the interest in thiazole derivatives for their antiviral properties.
Used in Anticancer Applications:
4-(3-Nitro-phenyl)-thiazol-2-ylamine is used as an intermediate in the development of anticancer agents, as thiazole derivatives have shown potential in this field.
Used in Agrochemicals:
4-(3-Nitro-phenyl)-thiazol-2-ylamine may be used in the development of agrochemicals, given its structural features that could be beneficial in this industry.
Used in Material Science:
4-(3-Nitro-phenyl)-thiazol-2-ylamine may also find applications in material science, due to its unique chemical structure and potential for creating new materials with specific properties.

InChI:InChI=1/C9H7N3O2S/c10-9-11-8(5-15-9)6-2-1-3-7(4-6)12(13)14/h1-5H,(H2,10,11)

Upstream product

• 17356-08-0 thiourea 
• 2227-64-7 3'-nitro-2-bromoacetophenone 
• 121-89-1 3-Nitroacetophenone 
• 199915-38-3 9-fluorenylmethoxycarbonyl isothiocyanate 
• 99-61-6 3-nitro-benzaldehyde 
• 3034-94-4 3-nitrophenylacetylene 
• 586-39-0 1-nitro-3-vinyl-benzene 
• 333-20-0 potassium thioacyanate 
• 121231-58-1 1-(1-azidovinyl)-3-nitrobenzene 
• 81585-69-5 2-iodo-1-(3-nitrophenyl)ethanone 

Downstream Products

• 87198-72-9 4-(3-nitrophenyl)-2-thiazolesulfamoylic acid 
• 6125-33-3 2-chloro-N-(4-(3-nitrophenyl)thiazol-2-yl)acetamide 
• 79652-50-9 7-{[4-(3-Nitro-phenyl)-thiazol-2-ylamino]-phenyl-methyl}-quinolin-8-ol 
• 103122-69-6 1-(4-Chloro-phenyl)-3-[4-(3-nitro-phenyl)-thiazol-2-yl]-urea 
• 172848-52-1 2-bromoacetylamino-4-(3-nitrophenyl)thiazole 
• 199666-03-0 3,4-dimethoxy-N-[4-(3-nitrophenyl)-2-thiazolyl]benzenesulfonamide 
• 199602-13-6 N-{4-[4-(3-nitro-phenyl)-thiazol-2-ylsulphamoyl]-phenyl}-acetamide 
• 944457-76-5 octanedioic acid [4-(3-nitro-phenyl)thiazol-2-yl]amide methyl ester 
• 944457-63-0 octanedioic acid [4-(3-nitro-phenyl)thiazol-2-yl]amide 
• 376349-14-3 N-[4-(3-nitrophenyl)-1,3-thiazol-2-yl][1,1'-biphenyl]-4-sulfonamide 
• 372094-22-9 N-[4-(3-Nitrophenyl)thiazol-2-yl]-(2-chloro-5-nitrophenyl)carboxamide 
• 1182243-19-1 4-(3-nitrophenyl)-N-(2-hydroxybenzylidene)thiazol-2-amine 

Relevant academic research and scientific papers

Novel thienopyrimidine-aminothiazole hybrids: Design, synthesis, antimicrobial screening, anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis and VEGFR-2 inhibition

A series of novel hybrid compounds of hexahydrobenzo[4,5]thieno[2,3-d]pyrimidine with aminothiazole scaffolds were synthesized. The synthesized compounds were evaluated for their cytotoxic activity against the NCI-60 human tumor cell line panel. Compounds 7c, 7d and 7e exhibited significant antiproliferative activities at 10?5 M dose. Compound 7c exhibited excellent cytotoxic activity against CNS cancer cell lines including SNB-75 and SF-295 as well as renal cancer cell line CAKI-1 when compared with sorafenib as standard anticancer drug. In addition, compound 7d showed almost comparable anticancer activity to sorafenib against SNB-75 cell line and displayed moderate activity against SF-295 and CAKI-1 cell lines in comparison to sorafenib. Compound 7c inhibited the vascular endothelial growth factor receptor 2 (VEGFR-2) with IC50 of 62.48 ± 3.7 nM and decreased both total VEGFR-2 and phosphorylated VEGFR-2 in treated SNB-75 cells suggesting its ability to down regulate cell proliferation, growth, and survival. The flow cytometric analysis showed that 7c displayed its cytotoxic activity through the reduction of the cellular proliferation and induction of cell cycle arrest at the G2/M phase. Compound 7c clearly boosted the level of the apoptotic caspase-3. All the synthesized compounds were also screened for their antibacterial and antifungal activity against four pathogenic strains of both Gram-positive and Gram-negative as well as Candida albicans. Only compound 7d exhibited antifungal activity against Candida albicans compared to nystatin as the standard antifungal compound.

Sodium alginate: Biopolymeric catalyst for the synthesis of 2-amino-4-arylthiazole derivatives in aqueous medium

Regarded as a naturally occurring macromolecule and without any post-modification, sodium alginate which possesses a granular form was found to be an efficient and recoverable bifunctional heterogeneous organocatalyst for the synthesis of 2-amino-4-arylthiazole derivatives was carried out by the reaction of substituted phenyl acetylene and thiourea in an eco-friendly condition in the presence of TBBDA (tetrabromobenzene-1,3-disulfonamide (tetrabromobenzene-1,3-disulfonamide). Mild reaction conditions, simple reaction procedure, easy purification, high yields of products, eco-friendly catalyst usage and convenient reusability are the highlighted points of this protocol.

Synthesis and evaluation of substituted aryl thiazoles with antioxidant potential as gastro-sparing anti-inflammatory agents

Background: NSAIDs are used as first-line drugs for the treatment of various inflammatory disorders. Chronic use of NSAIDs is known to be associated with gastrointestinal and renal toxicity. Local generation of reactive oxygen species finally resulting in cellular apoptosis is one of the accepted mechanisms for NSAID-induced toxicity. Objective: The objective of the present study was to design and synthesize a series of 2-methane sulfonamido substituted arylthiazole derivatives by including structural features of combined antiulcer and anti-inflammatory activity utilizing as the structural core, thiazole nucleus with potential for antioxidant effect. Methods: Compounds were designed based on three dimensional and field similarity studies. The synthesized compounds were evaluated for their anti-inflammatory activity in carrageenan-induced rat paw edema model. Rofecoxib and indomethacin were taken as standard drugs for comparison. The in vitro antioxidant activity was assessed in potassium ferricyanide reducing power (PFRAP) assay employing ascorbic acid as the standard drug. Results: The compounds 6 and 7 showed good anti-inflammatory activity comparable to the standard group and were also non ulcerogenic at the test doses. Compounds 1-7 displayed varying degrees of reducing power in the PFRAP) assay and the methanesulphonamido derivatives 4-7 showed the highest antioxidant activity (EC50 values 3.7-5.1 μmol/ml vs ascorbic acid 7.4 μmol/ml). Theoretical ADME profiling of the compounds based on selected physicochemical properties showed excellent compliance with Lipinski’s rule. Conclusion: A series of compounds have been designed and synthesized having dual antioxidant and anti-inflammatory activity with activities comparable to standard drugs.

Design, synthesis and molecular modelling studies of 1-methyl-3-(4-substituted phenyl-1,3thiazol-2-yl)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1h)-ones as potent anticancer agents

The present study involves the design, synthesis, characterization and molecular docking studies of biologically active quinazolin-4-ones, which were synthesized by condensing 2-amino-4-substituted phenylthiazole with N-methylbenzoxazin-4-one. The N-methylbenzoxazin-4-one and 2-amino-4-substituted phenylthiazole were synthesized from N-methylanthranilic acid and substituted ketones, respectively. The ADME properties determined the synthetic accessibility of quinazolin-4-ones by in silico Swiss ADME. The colorectal anticancer screening was done by using cell HT-29 human colorectal adenocarcinoma based on molecular docking studies on 3GC7-the structure of p38alpha in complex with dihydroquinazolinone. Finally, compounds 5Dh8, 5DF6, 5Db2 and 5Di9 exhibited better activity at a concentration 10 μg/mL when compared to 5-fluorouracil. The ADME properties revealed that all the compounds were within the range and docking studies showed the highest binding with glide score -7.19 and -7.027 Kcal/mol compared to the target protein -10.67 Kcal/mol.

Synthesis and Molecular Docking Studies of Some 1,2-Dimethyl-3(4-substituted phenyl-1,3-thiazol-2-yl)2,3-dihydroquinazolin-4(1H)-ones as Anticancer Agents

Synthesis of 1, 2-dimethyl-3(4-substituted phenyl-1,3-thiazol-2-yl)2,3-dihydro quinazolin-4(1H)-ones (5Aa1-5Ak11) derivatives was effected by refluxing 1,2-dimethylbenzoxazine-4-one with different 4-substituted phenyl-1,3-thiazol-2-amines. Synthesized compounds were characterized through elemental analysis, infrared, proton nuclear magnetic resonance, and Carbon-13 nuclear magnetic resonance. Molecular docking studies were carried out using Schr?dinger Glide (version 2020_1) which was docked into selective P38alpha and Activin A Receptor Type 1 (ACVR1) Activin receptor-like kinase-2 (ALK2) kinase with Protein Data Bank (PDB) code 3GC7, 6GI6. Based on the docking score of synthesized quinazolin-4-one derivatives, co-crystallized ligands interaction was evaluated with 5-fluorouracil (5-FU) as a reference drug. Compounds 5Ae5, 5Aa1, 5Ai9, and 5Ab2 with P38alpha, 5Af6, 5Ae5, 5Ad4, and 5Ab2 with ACVR1 (ALK2) kinase score were -7.265, -7.078, -7.058, and -6.836; -8.929, -8.749, -8.735, and -8.464 Kcal/mol against enzymes responsible for cancer treatment. The results indicated that quinazolin-4-one derivatives had scored better than ligand and 5-FU.

4-Phenylthiazole-2-amine derivative containing urea structure, and preparation method and application thereof

The invention discloses a 4-phenylthiazole-2-amine derivative containing a urea structure, and a preparation method and application thereof. The 4-phenylthiazole-2-amine derivative containing the ureastructure has a structure shown in a formula (I) below:

Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury

Myeloid differentiation primary response protein 88 (MyD88), an essential adapter protein used by toll-like receptors (TLR), is a promising target molecule for the treatment of respiratory inflammatory diseases. Previous studies explored the activities of novel 2-amino-4-phenylthiazole analogue (6) in inflammation-induced cancer, and identified the analogue as an inhibitor of MyD88 toll/interleukin-1 receptor (TIR) homology domain dimerization. Here, we describe the synthesis of 47 new analogues by modifying different sites on this lead compound and assessed their anti-inflammatory activities in lipopolysaccharide-induced mouse primary peritoneal macrophages (MPMs). The most promising compound, 15d, was found to effectively interact with MyD88 protein and prevented formation of the MyD88 homodimeric complex. Furthermore, 15d showed in vivo anti-inflammatory activity in LPS-caused model of acute lung injury. This work provides new candidates as MyD88 inhibitors to combat inflammation diseases.

Efficient thiazole-based polyimines as selective and reversible chemical absorbents for CO2 capture and separation: Synthesis, characterization and application

A new series of polyimines (PIMs-1-9) including ortho-linked thiazole units and flexible thioether linkages were synthesized from diamine monomers (DA-1-3) and some commercially available aromatic dialdehydes (terephthalaldehyde, isophthalaldehyde and 2,5

Design, synthesis, and anticancer activities of novel 2-amino-4-phenylthiazole scaffold containing amide moieties

Appropriately substituted 2-amino-4-phenylthiazole derivatives were designed and synthesized according to the structural characteristics of crizotinib. The obtained compounds were characterized using 1H NMR, 13C NMR, and HRMS. The ta

Β - secretase enzyme has the function of inhibiting compound, the preparation of the compounds and use thereof

The invention discloses a compound capable of inhibiting beta-secretase, and a preparation method and application thereof. The structure of the compound is shown in a formula I, formula II or formula III as described in the specification. In the formula I, X is S or NH; R1 is selected from hydrogen and nitro group; R2 and R4 are same or different and independently selected from the group consisting of hydrogen, halogen, nitro group and substituted aryl group; R3 is selected from the group consisting of hydrogen, nitro group, straight-chain and branched-chain alkyl and substituted alkyl groups with a carbon number of 1 to 4, alkylamino or alkyloxy group with a carbon number of 1 to 4 and alkylamido group with a carbon number of 1 to 4; R is located at position 2, 3 or 4 of a benzene ring and selected from the group consisting of hydrogen, straight-chain and branched-chain alkyl and substituted alkyl groups with a carbon number of 1 to 4, alkylamino or alkyloxy group with a carbon number of 1 to 4 and alkylamido group with a carbon number of 1 to 4. In the formula II, R is selected from different substituted aryl groups. In the formula III, R is selected from hydrogen or cyano group. Experiments prove that the compound provided by the invention has good beta-secretase inhibitory activity and has wide application values as a beta-secretase inhibitor.