28989-50-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Thiophen-2-yl-thiazol-2-ylamine is used as a potential drug candidate for the treatment of cancer due to its ability to inhibit mitochondrial complex I and induce reactive oxygen species (ROS) production, leading to apoptosis in cancer cells.
Used in Photodynamic Therapy:
TTFA is used as a potential photosensitizer in photodynamic therapy, where it can be activated by light to produce a therapeutic effect, particularly in the treatment of cancer.
Used in Antimicrobial Applications:
4-Thiophen-2-yl-thiazol-2-ylamine is being studied for its antifungal and antibacterial properties, indicating its potential use as an antimicrobial agent in various medical applications.
Used in Drug Development Research:
TTFA is utilized in research for drug development, given its unique chemical structure and biological activities, which may lead to the discovery of new therapeutic agents for a range of diseases.

InChI:InChI=1/C7H6N2S2/c8-7-9-5(4-11-7)6-2-1-3-10-6/h1-4H,(H2,8,9)

Upstream product

• 88-15-3 2-Acetylthiophene 
• 17356-08-0 thiourea 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 10531-41-6 2-Bromoacetylthiophene 
• 55984-19-5 2-iodo-1-(thiophen-2-yl)ethanone 
• 81447-27-0 2-tosyloxy-1-(2-thiophenyl)ethanone 

Downstream Products

• 100728-78-7 4-(2-amino-4-[2]thienyl-thiazol-5-ylazo)-benzenesulfonic acid amide 
• 101102-03-8 N-acetyl-sulfanilic acid-(4-[2]thienyl-thiazol-2-ylamide) 
• 313549-81-4 N-[4-(2-Thienyl)thiazol-2-yl)-(2-chloro-5-nitrophenyl)carboxamide 
• 85242-87-1 5-Phenylazo-4-thiophen-2-yl-thiazol-2-ylamine 

Relevant academic research and scientific papers

Anticancer and antimicrobial activities of new thiazolyl-urea derivatives: gene expression, DNA damage, DNA fragmentation and SAR studies

The drug resistance became the major challenge in the antimicrobial and anticancer drugs therapy. Therefore, there is an urgent need to looking for new types of antimicrobial and anticancer agents. Herein we reported the synthesis and biological evaluatio

Design, synthesis, antibacterial activity evaluation and molecular modeling studies of new sulfonamides containing a sulfathiazole moiety

Sulfonamides represent the oldest synthetic antibacterial agents; however, their central position in controlling bacterial diseases has been seriously damaged by the development of widespread resistance. Herein, we revisited sulfathiazole, a commercial member of antibacterial sulfa drugs, intending to overcome sulfonamide resistance and identify new drug candidates through molecular modifications. We synthesized twelve sulfonamides (SA1-SA12) by replacing the amino group on the phenyl ring with various substituents and introducing a thiophene ring on the core scaffold of sulfathiazole. The obtained compounds and additionally two commercial sulfonamides, sulfathiazole and sulfadiazine, were extensively screened for their antimicrobial activities. The results indicated that new sulfonamides, unlike traditional ones, were selectively effective against various Staphylococcus aureus strains. Introducing a bulky lipophilic substituent at the para position of the phenyl ring significantly increased the antibacterial activities of the compounds against Staphylococcus aureus. The compounds demonstrating favourable selectivity indices were further evaluated for their membrane potential perturbation and DNA interaction properties. The obtained data showed that these are not supporting mechanisms for the antibacterial activities of the modified sulfathiazole derivatives. In order to rationalize the activity of the three most active compounds, SA7, SA11 and SA12, against S. aureus ATCC 25923, their binding hypotheses within the catalytic site of Staphylococcus aureus dihydropteroate synthase, the validated target enzyme of sulfonamides, were generated via molecular docking and further dissected using molecular dynamics simulations and dynamic 3D pharmacophores (dynophores).

Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas

Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(II) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity, providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance.

Novel green synthesis method for efficiently synthesizing aminothiazole derivatives through transition metal catalyzed carbene insertion/cyclization reaction

The invention relates to a novel green synthesis method for efficiently synthesizing aminothiazole derivatives through transition metal catalyzed carbene insertion/cyclization reaction. According to the method, sulfur ylide serves as a carbene donor, carbene is catalyzed by a transition metal to be subjected to an insertion/cyclization reaction, a C-S bond is efficiently formed, and the 2-aminothiazole derivative is constructed. Compared with the traditional method, the method has the advantages that the raw materials are easy to obtain, the steps are simple, the mild sulfur ylide reagent is used for replacing a halogenating reagent required in the traditional synthesis method, and the method is a mild, quick, simple, convenient, effective and environment-friendly method for preparing the2-aminothiazole and the derivative thereof and has a wide application prospect.

SUBSTITUTED AMINOTHIAZOLES AS INHIBITORS OF NUCLEASES

The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3, R4, R5, R6 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.

Preparation of 3,4-Substituted-5-Aminopyrazoles and 4-Substituted-2-Aminothiazoles

3,4-Substituted-5-aminopyrazoles and 4-substituted-2-aminothiazoles are frequently used intermediates in medicinal chemistry and drug discovery projects. We report an expedient flexible synthesis of 3,4-substituted-5-aminopyrazoles (35 examples), based on palladium-mediated α-arylation of β-ketonitriles with aryl bromides. A library of 4-substituted-2-aminothiazoles (21 examples) was assembled by a sequence employing Suzuki coupling of newly prepared, properly protected pinacol ester and MIDA ester of 4-boronic acid-2-aminothiazole with (hetero)aryl halides.

Citric Acid-catalyzed Synthesis of 2,4-Disubstituted Thiazoles from Ketones via C–Br, C–S, and C–N Bond Formations in One Pot: A Green Approach

An improved and greener protocol has been developed for the synthesis of 2,4-disubstituted thiazoles via C–Br, C–S, and, C–N bond formations in a single step from readily available ketones, N-bromosuccinimide (NBS), and thiourea catalyzed by citric acid in a mixture of ethanol and water (3:1) under reflux conditions. This method has the advantages of freedom from the isolation of lachrymatory α-bromoketones, ease of carrying out, cleaner reaction profile, broad substrate scope, freedom from chromatographic purification, and suitability for large-scale synthesis.

Synthesis and evaluation of 5,6-disubstituted thiopyrimidine aryl aminothiazoles as inhibitors of the calcium-activated chloride channel TMEM16A/Ano1

Transmembrane protein 16A (TMEM16A), also called Ano1, is a Ca2+ activated Cl? channel expressed widely in mammalian epithelia, as well as in vascular smooth muscle and some tumors and electrically excitable cells. TMEM16A inhibitors have potential utility for treatment of disorders of epithelial fluid and mucus secretion, hypertension, some cancers and other diseases. 4-Aryl-2-amino thiazole T16Ainh-01 was previously identified by high-throughput screening. Here, a library of 47 compounds were prepared that explored the 5,6-disubstituted pyrimidine scaffold found in T16Ainh-01. TMEM16A inhibition activity was measured using fluorescence plate reader and short-circuit current assays. We found that very little structural variation of T16Ainh-01 was tolerated, with most compounds showing no activity at 10 μM. The most potent compound in the series, 9bo, which substitutes 4-methoxyphenyl in T16Ainh-01 with 2-thiophene, had IC50 ～1 μM for inhibition of TMEM16A chloride conductance.

Ionic liquid phase synthesis (IoLiPS) of 2-aminothiazoles and imidazo[1,2-a]pyridines

An efficient and practical ionic liquid phase synthesis (IoLiPS) of aza-heterocycles has been developed through a 'catch-and-release' strategy using an ionic liquid-supported hypervalent iodine reagent. The hypervalent iodine played a dual role as a reagent and as a soluble support. This strategy provided a combinatorial approach for the synthesis of 2-aminothiazoles and imidazo[1,2-a]pyridines directly from substituted acetophenones in good to excellent yields. The use of an ionic liquid supported reagent offered better isolation of the products by simple extraction with organic solvents. This journal is

Convenient and simple synthesis of 2-aminothiazoles by the reaction of α-halo ketone carbonyls with ammonium thiocyanate in the presence of N-methylimidazole

Substituted 2-aminothiazole derivatives were obtained as a result of N-methylimidazole catalyzed cyclization of α-halo ketone carbonyls with ammonium thiocyanate in water-alcoholic media. The generality of the method has been demonstrated by screening a series of aromatic/heteroaromatic/aliphatic α-halo ketones, α-halo β-diketones, and α-halo β-ketoesters. The developed method is simple, mild, and general route for the preparation of diversely functionalized 2-aminothiazoles in good to moderate yields from readily available starting materials.