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

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

Downstream Products

• 301859-89-2 N-[4-(4-Nitrophenyl)thiazol-2-yl]-(2-chloro-5-nitrophenyl)carboxamide 
• 3673-53-8 2-amino-4-(4-amino-phenyl)-thiazole 
• 83758-18-3 ethyl N-(4-p-nitrophenyl-2-thiazolyl)carbamate 
• 1223515-82-9 C₁₄H₈N₄O₃S₂ 
• 53101-19-2 N-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]acetamide 

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

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.

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.

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.

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.

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.

Chemical synthesis, molecular modeling and pharmacophore mapping of new pyrrole derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth

Abstract: Substituted phenylthiazolyl benzamide and pyrrolyl benzamide derivatives were developed using molecular hybridization technique to create novel lead antimycobacterial molecules used to fight against Mycobacteriumtuberculosis. The newly synthesized molecules have inhibited InhA, the enoyl-ACP reductase enzyme from the mycobacterial type II fatty acid biosynthetic pathway. Of these, compound 3b showed H-bonding interactions with Tyr158 and co-factor NAD+ that binds the active site of InhA. All the molecules were screened for in vitro antitubercular activity against M. tuberculosis H37Rv, as well as some representative molecules as the inhibitors of InhA. Thirteen compounds exhibited good anti-TB activities (MIC = 1.6 μg/mL), but only few representative molecules showed the moderate InhA enzyme inhibition activity. [Figure not available: see fulltext.].