57634-55-6

Usage

Uses

Used in Pharmaceutical Research:
4-(2-AMINO-THIAZOL-4-YL)-PHENOL is used as a building block for the synthesis of various drug compounds due to its unique structure and properties, which contribute to the development of new therapeutic agents.
Used in Antioxidant Applications:
4-(2-AMINO-THIAZOL-4-YL)-PHENOL is used as an antioxidant agent for its potential to combat oxidative stress, which is implicated in various diseases and aging processes.
Used in Antibacterial Applications:
4-(2-AMINO-THIAZOL-4-YL)-PHENOL is used as an antibacterial agent, leveraging its potential to inhibit bacterial growth, which can be beneficial in the development of new antimicrobial drugs.
Used in Drug Discovery and Development:
4-(2-AMINO-THIAZOL-4-YL)-PHENOL is used as a valuable tool in drug discovery and development, facilitating the identification and optimization of new therapeutic agents with improved efficacy and safety profiles.
Used in Treatment of Medical Conditions:
4-(2-AMINO-THIAZOL-4-YL)-PHENOL is used as a potential therapeutic agent for the treatment of certain medical conditions, based on its demonstrated promise in preliminary studies and investigations.

InChI:InChI=1/C9H8N2OS/c10-9-11-8(5-13-9)6-1-3-7(12)4-2-6/h1-5,12H,(H2,10,11)

Upstream product

• 17356-08-0 thiourea 
• 99-93-4 4-Hydroxyacetophenone 
• 1071-86-9 bis(formamidine)disulphide dihydrobromide 
• 99233-31-5 1-(4-hydroxyphenyl)-2-iodoethanone 
• 2491-38-5 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 2104-04-3 4-(4-methoxyphenyl)-1,3-thiazol-2-amine 
• 420-04-2 CYANAMID 
• 123-08-0 4-hydroxy-benzaldehyde 
• 2200-91-1 4-ethynylphenol 
• 7339-87-9 4-hydroxyphenylacetaldehyde 

Downstream Products

• 103155-06-2 7-{[4-(4-hydroxy-phenyl)-thiazol-2-ylamino]-methyl}-quinolin-8-ol 
• 103096-78-2 3-[4-(4-hydroxy-phenyl)-thiazol-2-ylamino]-1-phenyl-propan-1-one 
• 50728-79-5 3,5-dichloro-2-hydroxy-N-[4-(4-hydroxy-phenyl)-thiazol-2-yl]-benzamide 
• 74675-81-3 3,5-dibromo-2-hydroxy-N-[4-(4-hydroxy-phenyl)-thiazol-2-yl]-benzamide 
• 57634-48-7 4-(2-amino-5-chloro-thiazol-4-yl)-phenol 
• 79615-43-3 2-amino-4-<4-(2-thienylmethoxy)phenyl>thiazole 
• 79667-26-8 7-{[4-(4-Hydroxy-phenyl)-thiazol-2-ylamino]-phenyl-methyl}-quinolin-8-ol 
• 112635-04-8 2-hippurylamino-4-p-hydroxyphenylthiazole 
• 103726-76-7 4-[2-Amino-4-(4-hydroxy-phenyl)-thiazol-5-ylazo]-N-thiazol-2-yl-benzenesulfonamide 
• 103726-71-2 4-[2-Amino-4-(4-hydroxy-phenyl)-thiazol-5-ylazo]-N-pyrimidin-2-yl-benzenesulfonamide 
• 103726-72-3 4-[2-Amino-4-(4-hydroxy-phenyl)-thiazol-5-ylazo]-N-(2-methyl-pyrimidin-4-yl)-benzenesulfonamide 
• 103726-75-6 4-[2-Amino-4-(4-hydroxy-phenyl)-thiazol-5-ylazo]-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide 
• 103740-33-6 4-[2-Amino-4-(4-hydroxy-phenyl)-thiazol-5-ylazo]-N-(3,4-dimethyl-isoxazol-5-yl)-benzenesulfonamide 
• 103726-74-5 4-[2-Amino-4-(4-hydroxy-phenyl)-thiazol-5-ylazo]-N-(6-methoxy-pyridazin-3-yl)-benzenesulfonamide 

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.]

In vitro anticancer activity of thiazole based β-amino carbonyl derivatives against HCT116 and H1299 colon cancer cell lines; study of pharmacokinetics, physicochemical, medicinal properties and molecular docking analysis

The present study describes the synthesis and anticancer evaluation of certain substituted rac-(2S)-2-[(R)-[(4-substitutedphenyl){[4-(4-substitutedphenyl)-1,3-thiazol-2-yl]amino}methyl]cyclohexanone derivatives. The in vitro anticancer assay indicating su

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.

Biological evaluation and synthesis of thiazole schiff base derivatives

In this study, we report the synthesis of thiazole Schiff base derivatives (Z1-Z16) and their tyrosinase inhibitory activity, anti-oxidant activities. Mushroom tyrosinase inhibitory assay showed compound Z8 (IC50 = 2.78 ± 0.08 μM) inhibited tyrosinase more than kojic acid (49.39 ± 0.17 μM), and docking study indicated compound Z8 (-7.32 kcal/mol) had stronger binding affinities for tyrosinase than kojic acid (-5.7 kcal/mol). Phenolic hydroxyl group on 4-position (R2) of compound Z8 can form Metal - Acceptor with Cu401. The results of inhibition kinetics studies demonstrated that compound Z8 was mixed type inhibitor. The anti-browning effects manifested compound Z8 expressed satisfactory effects in anti-browning of fresh-cut apples and fresh-cut potato. All the results indicated that thiazole Schiff base derivatives might be promising leading compounds as tyrosinase inhibitors and anti-oxidant agents.

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.

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.

Structure-Based Design of N-(5-Phenylthiazol-2-yl)acrylamides as Novel and Potent Glutathione S-Transferase Omega 1 Inhibitors

Using reported glutathione S-transferase omega 1 (GSTO1-1) cocrystal structures, we designed and synthesized acrylamide-containing compounds that covalently bind to Cys32 on the catalytic site. Starting from a thiazole derivative 10 (GSTO1-1 IC50 = 0.6 μM), compound 18 was synthesized and cocrystallized with GSTO1. Modification on the amide moiety of hit compound 10 significantly increased the GSTO1-1 inhibitory potency. We solved the cocrystal structures of new derivatives, 37 and 44, bearing an amide side chain bound to GSTO1. These new structures showed a reorientation of the phenyl thiazole core of inhibitors, 37 and 44, when compared to 18. Guided by the cocrystal structure of GSTO1:44, analogue 49 was designed, resulting in the most potent GSTO1-1 inhibitor (IC50 = 0.22 ± 0.02 nM) known to date. We believe that our data will form the basis for future studies of developing GSTO1-1 as a new drug target for cancer therapy.

Asparagine functionalized Al2O3 nanoparticle as a superior heterogeneous organocatalyst in the synthesis of 2-aminothiazoles

Asparagine functionalized aluminum oxide nanoparticles (Asp-Al2O3) have been prepared by a two-step procedure involving the grafting of Al2O3 with 3-chloropropyltrimethoxysilane (CPTMS) and subsequent organofunctionalization using asparagine amino acid. It is shown that Asp-Al2O3 exhibits as an active nanocatalyst for the preparation of 2-aminothiazoles is achieved by one-pot reaction of methylcarbonyls, thiourea and iodine. The structure of Asp-Al2O3 was characterized by fourier transform infrared radiation (FT-TR), thermal gravimetric analysis (TGA), X-ray diffraction (XRD), scanning electron microscopic (SEM), and energy-dispersive analysis of X-ray (EDAX) analyses. Advantages of this modified methodology include higher purity and excellent yield of products, greener and cleaner conditions, easy isolation of products and convenient manipulation. Moreover, immobilization of organocatalysts on the Al2O3 surface are stable under the catalytic reaction conditions resulting their efficient reuse.

Thiazole drug molecule with bactericidal activity and preparation method thereof

The invention discloses a thiazole drug molecule with bactericidal activity and a preparation method thereof, and belongs to the technical field of synthesis of antibacterial drugs. The thiazole drugmolecule is technically characterized in that the thiazole drug molecule has a structure, wherein R represents methyl, hydroxyl or nitro. According to the thiazole drug molecule, 4-methylacetophenoneis used as an initial raw material, 4-(4-methylbenzene)-thiazole-2-amine is obtained through primary cyclization at first, 3-(4-methylbenzene)-5H-thiazole[3,2-a]pyrimidin-5-ketone is obtained throughsecondary cyclization, 6-hydroxymethyl-3-(4-methylbenzene)-5H-thiazole[3,2-a]pyrimidin-5-ketone is obtained through a reaction with paraformaldehyde, and finally, a target compound is obtained throughtwo-step oxidation, one-step acylation and other processes. An antibacterial activity test is carried out through an Oxford cup agar diffusion method, and it is found that the target compound has a good inhibition effect on escherichia coli and bacillus subtilis.

MNPs@SiO2-Pr-AP: A new catalyst for the synthesis of 2-amino-4-aryl thiazole derivatives

A simple and efficient synthesis of 2-amino-4-aryl thiazole derivatives was carried out through the reaction of substituted acetophenones and thiourea using three different types of catalytic systems including N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N,N′-dibromo-N-ethylbenzene-1,3-disulfonamide) [PBBS] and a combination of TBBDA and nano-magnetic catalyst supported with functionalized 4-amino-pyridine silica (MNPs@SiO2-Pr-AP). The results showed that the use of TBBDA along with the MNPs@SiO2-Pr-AP gains the highest yields of the products in the shortest reaction time.