2104-09-8

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-NITRO-PHENYL)-THIAZOL-2-YLAMINE is used as a reagent for the preparation of 2-aminothiazole derivatives with biological properties. These derivatives are of interest due to their potential therapeutic applications, including the development of new drugs for various medical conditions.
Used in Chemical Research:
In the field of chemical research, 4-(4-NITRO-PHENYL)-THIAZOL-2-YLAMINE serves as a key intermediate for the synthesis of novel compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science. Its unique structure allows for further functionalization and exploration of its chemical properties.
Used in Material Science:
4-(4-NITRO-PHENYL)-THIAZOL-2-YLAMINE may also find applications in the development of new materials with specific properties, such as optical, electronic, or magnetic characteristics. Its incorporation into polymers or other materials could lead to the creation of advanced materials with tailored properties for various applications.

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

Upstream product

• 100-19-6 (4-nitrophenyl)ethanone 
• 4203-31-0 2-diazo-1-(4-nitrophenyl)ethanone 
• 17356-08-0 thiourea 
• 100-12-9 4-ethylnitrobenzene 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 420-04-2 CYANAMID 
• 100-13-0 4-nitrostyrene 
• 122-04-3 4-nitro-benzoyl chloride 
• 99-81-0 4-Nitrophenacyl bromide 
• 34006-49-0 2-chloro-1-(4-nitrophenyl)ethanone 
• 64-17-5 ethanol 

Downstream Products

• 37614-91-8 2-chloro-N-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]acetamide 
• 92537-75-2 3-(4-Nitro-phenyl)-7-oxo-7H-thiazolo[3,2-a]pyrimidine-5-carboxylic acid ethyl ester 
• 53101-19-2 N-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]acetamide 
• 301859-89-2 N-[4-(4-Nitrophenyl)thiazol-2-yl]-(2-chloro-5-nitrophenyl)carboxamide 
• 102300-80-1 5-nitro-4-(4-nitrophenyl)-1,3-thiazol-2-amine 

Relevant academic research and scientific papers

Novel benzothiazole derivatives with a broad antifungal spectrum: Design, synthesis and structure-activity relationships

N-Myristoyltransferase (NMT) is a new target for the development of novel antifungal agents. The benzothiazole derivative FR1335 is a highly potent NMT inhibitor with fungicidal activity. However, FTR1335 was only active against Candida albicans and its a

Design, synthesis and biological screening of new 4-thiazolidinone derivatives with promising COX-2 selectivity, anti-inflammatory activity and gastric safety profile

Two series of new thiazolidin-4-one derivatives 4a-c and 8a-e were designed and prepared. All the synthesized compounds were evaluated for their in vitro COX-2 selectivity and anti-inflammatory activity in vivo. Compounds 8c and 8d showed the best overall

Efficient L-Proline catalyzed synthesis of some new (4-substituted-phenyl)-1,5-dihydro-2H-pyrimido[4,5-d][1,3]thiazolo[3,2a]-pyrimidine-2,4(3H)-diones bearing thiazolopyrimidine derivatives and evaluation of their pharmacological activities

In the present study, a simple and efficient protocol has been developed to synthesize a series of new (4-substituted-phenyl)-1,5-dihydro-2H-pyrimido[4,5-d][1,3]thiazolo[3,2a]-pyrimidine-2,4(3H)-dione derivatives (4a-g) through L-proline-catalyzed reactio

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.

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.

Novel synthesis of 2-Aminothiazoles via Fe(III)-Iodine-catalyzed Hantzsch-type condensation

A novel iron-iodine catalyzed one pot synthesis of 2-aminothiazoles from methyl aryl ketones and thiourea is demonstrated. This protocol can be considered as a catalyzed version of the classical Hantzsch aminothiazole synthesis as it enables the in situ generation of α-iodoketones in the reaction medium using catalytic amount of iodine leading to Hantzsch condensation with thiourea. The supply of iodine for multiple catalytic cycles is ensured by using catalytic amounts of iron as it enables iodide to iodine oxidation. The generality of this protocol is also well established in this manuscript by synthesizing a variety of 2-aminothiazoles from different ketones and thiourea.

New hybrids derived from the natural compound (-)-β-pinene and amides or acylthioureas as antitumor agents

Background: Plant-derived natural compounds have a unique molecular structure and rich biological activity, hence, they are treated as important raw materials for the development of drugs. Methods: A natural compound (-)-β-pinene was used as a raw material, and twenty-six novel derivatives with amide or acylthiourea groups were synthesized based on the molecular hybridization method. In vitro antitumor activity of these derivatives on human breast cancer cell line MCF7 and human colon cancer cell line SW1116 were tested by MTT method. The effects of the synthesized derivatives on the morphology of MCF7 and SW1116 were observed by fluorescent inverted microscope. Results: The preliminary structure-activity relationship analysis demonstrates that the position and species of substituents on the aromatic ring of derivatives have an effect on the antitumor activity of derivatives. Observation of the cell morphology reveals that derivatives with antitumor activity can lead to rounding of the cell morphology, a decrease in cell volume and cell density, and ultimately inhibition of the proliferation of MCF7 and SW1116 cells. The antitumor activity evaluation results show that among these derivatives, compounds 5c, 5e, 5h, 7c, 7b and 7e exhibit good antitumor activity against MCF7, and compounds 5c, 5e, 5h and 7j exert moderate antitumor activity against SW1116. Conclusion: This study hopes to promote the high value-added utilization of natural compounds β-pinene and the development of novel antitumor drugs.

Synthesis and biological evaluation of 2,4-disubstituted thiazole amide derivatives as anticancer agent

A series of novel 2,4-disubstituted thiazole amide derivatives were synthesized, and their antiproliferative activities were tested. Some of these compounds displayed good antiproliferative activity, especially for HT29 cell. Among these compounds, compound 5b inhibits A549, HeLa, HT29 and Karpas299 cells with IC50 values of 8.64, 6.05, 0.63 and 13.87?μM, respectively. The western blot analysis and docking study provide important clues for further optimization of compound 5b as a potential c-Met inhibitor.

Synthesis and biological evaluation of 2-chloro-3-[(thiazol-2-yl)amino]-1,4-naphthoquinones

A series of novel, substituted 2-chloro-3-[(thiazol-2-yl)amino]-1,4-naphthoquinones have been prepared and shown to exhibit promising concentration-dependent activity against human SH-SY5Y cells, Plasmodium falciparum, Mycobacterium tuberculosis and P. aeruginosa. Substituent effects on observed bioactivity have been explored; the para-fluorophenyl derivative 3d exhibited activity across the range of the bioassays employed, indicating the potential of the 2-chloro-3-[(4-arylthiazol-2-yl)amino]-1,4-naphthoquinone scaffold in the development of novel, broad spectrum therapeutics.

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas

Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.