17823-27-7

Basic information

• Product Name: 2-PHENYLAMINO-THIAZOL-4-ONE
• Synonyms: 2-Thiazolin-4-one,2-anilino- (8CI); 4-Thiazolidinone, 2-(phenylimino)- (6CI,7CI);2-(Phenylimino)-4-thiazolidinone; 2-Anilino-2-thiazolin-4-one;2-Anilinothiazolin-4-one; 2-Phenylpseudothiohydantoin
• CAS NO: 17823-27-7
• Molecular Formula: C₉H₈N₂OS
• Molecular Weight: 0
• Mol File: 17823-27-7.mol

Chemical Properties

• Boiling Point: 313.3°Cat760mmHg
• Flash Point: 143.3°C
• Appearance: /
• Density: 1.4g/cm³
• Vapor Pressure: 0.000307mmHg at 25°C
• Refractive Index: 1.682
• CAS DataBase Reference: 2-PHENYLAMINO-THIAZOL-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYLAMINO-THIAZOL-4-ONE(17823-27-7)
• EPA Substance Registry System: 2-PHENYLAMINO-THIAZOL-4-ONE(17823-27-7)

Safety Data

• Hazardous Substances Data: 17823-27-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-PHENYLAMINO-THIAZOL-4-ONE is used as a pharmaceutical drug candidate for its potential therapeutic properties. It is valued for its ability to be developed into new medications or serve as an intermediate in the synthesis of other bioactive compounds, contributing to the advancement of medical treatments.
Used in Chemical Synthesis:
In the field of organic chemistry, 2-PHENYLAMINO-THIAZOL-4-ONE is used as a building block for the synthesis of other organic compounds. Its unique structure allows for the creation of a variety of chemical entities, expanding the scope of chemical research and development.
Used as a Corrosion Inhibitor:
2-PHENYLAMINO-THIAZOL-4-ONE is utilized as a corrosion inhibitor in industrial applications. Its properties enable it to protect materials from degradation due to corrosive agents, thereby extending the lifespan of equipment and structures in various industries.
Used in Academic Research:
In academic settings, 2-PHENYLAMINO-THIAZOL-4-ONE serves as a subject of study for researchers exploring the properties and potential applications of thiazole compounds. Its role in academic research aids in the discovery of new chemical reactions and the development of innovative synthetic pathways.

InChI:InChI=1/C9H8N2OS/c12-8-6-13-9(11-8)10-7-4-2-1-3-5-7/h1-5H,6H2,(H,10,11,12)

Upstream product

• 141-84-4 2-thioxo-4-thiazolidinone 
• 62-53-3 aniline 
• 6966-55-8 2-imino-3-phenyl-4-thiazolidinone 
• 556-90-1 pseudothiohydantoin 
• 1132-44-1 1-acetyl-3-phenylthiourea 
• 102-15-8 phenylcarbamimidoylmercapto-acetic acid 
• 68-11-1 mercaptoacetic acid 
• 622-34-4 1-phenylcyanamide 
• 105-39-5 chloroacetic acid ethyl ester 
• 103-85-5 monophenylthiourea 
• 333-20-0 potassium thioacyanate 
• 587-65-5 N-chloroacetyl-aniline 
• 17356-08-0 thiourea 
• 79-11-8 chloroacetic acid 

Downstream Products

• 107524-04-9 (5Z)-5-(1,3-benzodioxol-5-ylmethylidene)-2-phenylamino-1,3-thiazol-4(5H)-one 
• 100881-05-8 4-(2-anilino-4-oxo-4,5-dihydro-thiazol-5-yl)-benzenesulfonic acid 
• 109963-64-6 [4-(2-anilino-4-oxo-4,5-dihydro-thiazol-5-yl)-phenyl]-arsonic acid 
• 109649-34-5 2-anilino-5-[(1,3-dimethyl-1,3-dihydro-benzimidazol-2-yliden)-ethylidene]-thiazol-4-one 
• 92796-71-9 2-anilino-5-(2-chloro-benzylidene)-thiazol-4-one 
• 34761-21-2 2-anilino-5-(3-nitro-benzylidene)-thiazolidin-4-one 
• 38771-64-1 2-anilino-5-benzylidene-thiazol-4-one 
• 94205-70-6 2-anilino-5-(4-hydroxy-benzylidene)-thiazol-4-one 
• 94205-71-7 2-anilino-5-salicylidene-thiazol-4-one 
• 2295-31-0 thiazoline-2,4-dione 
• 1010-53-3 3-phenyl-2,4-thiazolidinedione 
• 27472-71-5 2-anilino-5-(5-nitro-furan-2-ylmethylene)-thiazol-4-one 
• 93989-47-0 5-(4-chlorobenzylidene)-2-(phenylimino)thiazolidin-4-one 
• 92796-71-9 2-anilino-5-(2-chloro-benzylidene)-thiazol-4-one 

Relevant articles and documents

Structure-Activity Relationship in the Leucettine Family of Kinase Inhibitors

The protein kinase DYRK1A is involved in Alzheimer's disease, Down syndrome, diabetes, viral infections, and leukemia. Leucettines, a family of 2-aminoimidazolin-4-ones derived from the marine sponge alkaloid Leucettamine B, have been developed as pharmacological inhibitors of DYRKs (dual specificity, tyrosine phosphorylation regulated kinases) and CLKs (cdc2-like kinases). We report here on the synthesis and structure-activity relationship (SAR) of 68 Leucettines. Leucettines were tested on 11 purified kinases and in 5 cellular assays: (1) CLK1 pre-mRNA splicing, (2) Threonine-212-Tau phosphorylation, (3) glutamate-induced cell death, (4) autophagy and (5) antagonism of ligand-activated cannabinoid receptor CB1. The Leucettine SAR observed for DYRK1A is essentially identical for CLK1, CLK4, DYRK1B, and DYRK2. DYRK3 and CLK3 are less sensitive to Leucettines. In contrast, the cellular SAR highlights correlations between inhibition of specific kinase targets and some but not all cellular effects. Leucettines deserve further development as potential therapeutics against various diseases on the basis of their molecular targets and cellular effects.

Synthesis and exploration of configurational dynamics in equilibrating E/Z 2-aryliminothiazolidin-4-ones using NMR and estimation of thermodynamic parameters

In the present study, 2-aryliminothiazolidin-4-ones (3 and 5) were utilized as dynamic chemical systems, whose different states are modulated in a reversible fashion through specific chemical stimuli. The in-depth NMR investigation revealed that the magnitude of rotational energy barrier (ΔG?) is affected markedly by (1) the solvent polarity; (2) the electronic nature of the ring system present on the exocyclic CQN bond and (3) the temperature of the system. The derivatives of 5-(3-arylallylidene)-2-(arylimino)thiazolidin-4-one exist in two isomeric forms at room temperature in DMSO-d6: (2E,5Z,7E) ? (2Z,5Z,7E). The stereodynamics of the synthesized derivatives (5a-5t) has been investigated using variable temperature dynamic 1H-NMR (VT DNMR). The ΔG? values (≈15 kcal mol?1) estimated for the dynamic process depict a significant barrier between two forms in solution at ambient temperature. To go a step further, line shape analysis was also performed to get a clear understanding of the equilibration mechanism.

SO2F2-Mediated N-Alkylation of Imino-Thiazolidinones

The N-alkylation of ambident and weakly nucleophilic imino-thiazolidinones has been developed via substitution with alkyl fluorosulfonates. These reactive electrophiles are obtained through the transformation of nontoxic, economic, and commercially availa

Design and microwave synthesis of new (5z) 5-arylidene-2-thioxo-1,3-thiazolinidin-4-one and (5z) 2-amino-5-arylidene-1,3-thiazol-4(5h)-one as new inhibitors of protein kinase dyrk1a

Here, we report on the synthesis of libraries of new 5-arylidene-2-thioxo-1,3-thiazolidin-4-ones 3 (twenty-two compounds) and new 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones 5 (twenty-four compounds) with stereo controlled Z-geometry under microwave irradi

Synthesis of Novel Triazole Incorporated Thiazolone Motifs Having Promising Antityrosinase Activity through Green Nanocatalyst CuI-Fe3O4@SiO2 (TMS-EDTA)

In the present work, novel 5-((1-benzyl-1,2,3-triazol-4-yl)methoxybenzylidene)-2-(arylamino)thiazol-4-one thiazolone incorporated triazole derivatives have been designed as tyrosinase inhibitors. The compounds were synthesized through click reaction in good yield. Moreover, the antityrosinas activity of the synthesized derivatives was evaluated. In the search for establishing a click copper-catalyzed azide/alkyne cycloaddition (CuAAC) reaction under strict conditions, in terms of a novel air-stable, a recyclable and efficient magnetic catalyst was planned for new triazole derivatives as a well-organized copper iodide supported on the functionalized Fe3O4@SiO2 core-shell (CuI/Fe3O4@SiO2(TMS-EDTA) nanoparticles). The engineered nanocatalyst synthesized for the first time and characterized by different methods, including FT-IR spectroscopy, XRD, FESEM, EDX, TEM, TGA, and BET analysis. The excellent catalytic performance in ethanol with high surface area (351.7 m2g?1) and short reaction time for diverse functional groups (120–200 min), no use of toxic solvents, reusability of the catalyst, and using eco-friendly conditions are the advantageous of this work. Moreover,the nanocatalyst can be used at least five times without any significant decrease in the yield of the reaction. The thiazolidine-triazole derivatives 9a, 9c, 9e, and 9 g showed promising tyrosinase inhibitory activity with IC50 values in the range of 5.90–9.81 μM. The compounds were found to be considerably more potent tyrosinase inhibitors than the reference inhibitor kojic acid (IC50 = 18.36 μM).

Rhodium complex containing ortho-position carborane Schiff base ligand as well as preparation method and application thereof

The invention relates to a rhodium complex containing an ortho-position carborane Schiff base ligand as well as a preparation method and application thereof. The rhodium complex is prepared by the following steps: reacting ortho-position carborane diforma

New thiazolidine-2,4-dione derivatives combined with organometallic ferrocene: Synthesis, structure and antiparasitic activity

Favourable physicochemical properties of an organometallic ferrocene and antiplasmodial potency of compounds containing the thiazolidine-2,4-dione framework (TZD-4) prompted us to explore compounds containing both the thiazolidine-2,4-dione core and the ferrocenyl unit with the primary aim of identifying compounds with promising antiprotozoal activities. Thus, a new series of rationally designed ferrocene-based thiazolidine-2,4-dione derivatives, containing a selection of secondary cyclic amines, was synthesised and fully characterised using standard spectroscopic techniques. The resulting compounds were screened for their antiplasmodial and antitrypanosomal activities against both the chloroquine-resistant (Dd2) strain of Plasmodium falciparum and the Nagana Trypanosoma brucei brucei 427. The general trend that emerged indicated that the target compounds were more selective towards T. b. brucei compared to the P. falciparum parasite. Moreover, the analogues bearing methylpiperazine (8a) and piperidine (8b) rings were more active against T. b. brucei compared to hit compound TZD-4. Except compound 8b, which appeared promising, none of the synthesised compounds showed better activity than TZD-4 against the P. falciparum parasite. All the synthesised compounds were non-toxic and often showed >90% viability of the HeLa cell line screened.

Design, synthesis and molecular docking studies of some thiazole clubbed heterocyclic compounds as possible anti-infective agents

The present work describes synthesis of a series of 5-((1-(4-(4-chlorophenyl)thiazol-2-yl)-3- aryl-1H-pyrazol-4-yl)methylene)-2-(arylimino)thiazolidin-4-one derivatives and their molecular docking and biological evaluation as possible antimalarial, anthelmintic and antimicrobial agents. The synthesis of compounds has been accomplished by adopting suitable synthetic methods. Structures of newly synthesized compounds were characterized and authenticated by spectral methods such as IR, 1H-NMR and mass spectra. Synthesized compounds were screened for their in vitro antimicrobial activity against selected bacterial strains and fungal strains viz. B. subtilis, S. aureus, E. coli, P. fluorescens, C. albicans, C. glabrata and antimalarial studies against P. falciparum. Titled compounds were also tested against Pheretima posthuma (earthworm) for their anthelmintic activity. Molecular docking was done to study the binding modes of the potent compounds against Escherichia coli (PDB ID: 1AB4) and Candida P450DM (PDB ID: 1EA1) enzymes. The results revealed that all the compounds exhibited moderate to significant antimicrobial activities. Antimalarial activity screening revealed that one compound 8i showed significant antimalarial activity with of IC50; 0.59 μg/mL as compared to standard drugs chloroquine (IC50= 0.020 μg/mL) and quinine (IC50; 0.268 μg/mL). The most active compound exhibited the mean paralysis time of 19.2 ± 0.9 min and mean death time of 31.7 ± 2.5 min. It can be concluded that some of the synthesized compounds have remarkable antiinfective, antimalarial and anthelmintic activity and are suitable candidates for further scientific exploration.

Synthesis of thiazolone derivatives as novel soybean 15-LOX inhibitors

Background: Thiazole derivatives are known as important sulfur containing heterocycles which are present in a wide range of biologically active natural products. Methods: A series of thiazolone derivatives were synthesized and evaluated for their soybean 15-LOX inhibitory activity. The title compounds were prepared by the reaction of 2-arylthiazol-4(5H)-ones and different aromatic aldehydes. All compounds were characterized and evaluated against soybean 15-LOX. Results: Among the synthesized thiazolone derivatives, 5-(4-methoxybenzylidene)-2-((2-methoxyphenyl) amino)thiazol-4(5H)-one (3l) was found to be the most active compound comparing with quercetin as the reference drug. Conclusion: It seems that prepared thiazolones having methoxy groups both on aryl and aminoaryl moieties can be considered for further drug discovery research.

A 5 - (1 H - indole - 3 - methylene) - 1, 3 - thiazolidine - 4 - ketone derivative and its synthetic method and application

The invention relates to 5-(1H-indolyl-3-methylene)-1,3-thiazolidinyl-4-one derivatives, and a synthesis method and application thereof. By using ethanol and/or water as a solvent, substituted 2-substituted-imino-1,3-thiazolidinyl-4-one and 1H-indolyl-3-formaldehyde are subjected to reflux reaction under the catalytic condition of piperidine through intermolecular dehydration condensation reaction to form methylene linking group, thereby obtaining the 5-(1H-indolyl-3-methylene)-1,3-thiazolidinyl-4-one derivatives. The intermediate 2-substituted-iminothiazolidinyl-4-one is prepared by carrying out cyclization reaction on various monosubstituted ethyl thiocarbamide chloroacetates or chloroacetic acids in a low-boiling solvent under reflux conditions, and the intermediate 2-substituted-imino-3-substituted-1,3-thiazolidinyl-4-one is prepared by carrying out a green environment-friendly synthesis technique on various disubstituted symmetric thiocarbamides and chloroacetic acids. The bioactivity preliminary screening experiment result of all the target compounds on the enzyme molecular level indicates that the target products have certain inhibition activity on PTP1B and CDC25B to different degrees.