24045-15-6

Usage

Properties

1. Molecular Formula: \textC9\textH8\textN2\textO2\textS
2. Chemical Structure: Thiazole compound with a thiazole ring and an amino group attached to a phenyl ring.
3. Functional Groups:
Thiazole ring
Amino group (NH2)
Hydroxyphenyl group (phenyl ring with a hydroxy group)

Specific Content

1. Chemical Name: 2-[(4-Hydroxyphenyl)amino]-1,3-thiazol-4(5H)-one
2. Functional Description:
Thiazolone ring (1,3-thiazol-4(5H)-one)
Amino group attached to the phenyl ring (4-Hydroxyphenylamino)
Hydroxyphenyl compound due to the presence of a hydroxy group on the phenyl ring
3. Potential Applications:
Pharmaceuticals: Possible inhibitor of certain enzymes, building block for synthesizing other compounds.
Agrochemicals: Potential bioactive properties that could be beneficial.
4. Biological Activities:
Antioxidant: Potential antioxidant properties.
Antimicrobial: Possible antimicrobial effects.
5. Research Needs:
Further research is required to fully understand its range of potential uses and effects.

2-[(4-HYDROXYPHENYL)AMINO]-1,3-THIAZOL-4(5H)-ONE's unique structure and functional groups make it promising for various applications in pharmaceuticals, agrochemicals, and potentially other fields. However, detailed research and testing are necessary to explore its full potential and effects.

Upstream product

• 123-30-8 4-amino-phenol 
• 51126-34-2 ethyl 2-(4-oxo-4,5-dihydrothiazol-2-ylthio)acetate 
• 1520-27-0 1-(4-hydroxyphenyl)thiourea 
• 79-11-8 chloroacetic acid 
• 105-39-5 chloroacetic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of 5-arylidene-2-amino-4-azolones and evaluation of their anticancer activity

Series of novel 5-arylidene-2-arylaminothiazol-4(5H)-ones and 2-aryl(benzyl)amino-1H-imidazol-4(5H)-ones were synthesized from appropriate 2-alkylthioazol-4-ones using nucleophilic substitution in position 2 by various anilines and benzylamines and Knoeve

Design, synthesis, cytoselective toxicity, structure-activity relationships, and pharmacophore of thiazolidinone derivatives targeting drug-resistant lung cancer cells

Ten cytoselective compounds have been identified from 372 thiazolidinone analogues by applying iterative library approaches. These compounds selectively killed both non-small cell lung cancer cell line H460 and its paclitaxel-resistant variant H460taxR at an IC50 between 0.21 and 2.93 μM while showing much less toxicity to normal human fibroblasts at concentrations up to 195 μM. Structure-activity relationship studies revealed that (1) the nitrogen atom on the 4-thiazolidinone ring (ring B in Figure 1) cannot be substituted, (2) several substitutions on ring A are tolerated at various positions, and (3) the substitution on ring C is restricted to the -NMe2 group at the 4-position. A pharmacophore derived from active molecules suggested that two hydrogen bond acceptors and three hydrophobic regions were common features. Activities against P-gp-overexpressing and paclitaxel-resistant cell line H460taxR and modeling using a previously validated P-gp substrate pharmacophore suggested that active compounds were not likely P-gp substrates.

Synthesis and antiinflammatory activity of some 2-arylamino-2-thiazoline-4-ones

A mild and efficient method of synthesis of 2-arylamino-2-thiazoline-4-ones was established using 2-carboethoxymethylthio-2-thiazolin-4-one (II) as a key intermediate. Reaction of 2-carboethoxymethylthio-2-thiazolin-4-one with m- or p-aminophenole afforded 2-(3-or4-oxyphenylamino)-2-thiazoline-4-ones (V, XV). Condensation of V, XV with aromatic aldehydes, according to the Knoevenagel, gives respective 5-arylidene derivatives V-XIII, XVI-XXIX, which were obtained alternatively using m- or p-oxyarylthioureas. 5-Carboxymethylderivatives XIV, XXX were synthesized by condensation of arylthioureas and maleic anhydride in acetic acid. Quantum-chemical calculations were made to confirm the possibility of dynamic amino-imino tautomerism of synthesized compounds. Structure and tautomerism of the obtained substances were confirmed by UV, IR, MS and NMR spectra. Biological activity prediction using the computer program PASS C&T has been made. According to these prediction results, some compounds were tested in vivo for their antiinflammatory activity. 5-[2-Chloro-3-(4-nitrophenyl)-2-propenilidene] -2-(3-hydroxyanilino)-2-thiazoline-4-one (XII) possess significant antiinflammatory effect in comparison with diclofenac sodium, aspirin, acetaminofen and phenylbutazone.