3292-77-1

Usage

Uses

Used in Pharmaceutical Industry:
2-BROMO-1-(1,3-THIAZOL-2-YL)ETHANONE is used as a key intermediate in the synthesis of biologically active compounds, contributing to the development of new drugs. Its unique structure allows for the creation of molecules with potential therapeutic properties, making it an essential component in the advancement of pharmaceutical research and development.
Used in Agrochemical Industry:
In the agrochemical sector, 2-BROMO-1-(1,3-THIAZOL-2-YL)ETHANONE serves as a crucial intermediate for the synthesis of new pesticides. Its versatile nature enables the development of innovative molecules with enhanced pesticidal properties, addressing the evolving needs of agriculture and contributing to more effective pest control solutions.
Used in Chemical Research and Development:
2-BROMO-1-(1,3-THIAZOL-2-YL)ETHANONE is utilized as a significant compound in the field of chemical research and development. Its unique structure and functional groups make it an ideal candidate for exploring new chemical reactions and synthesizing novel compounds with potential applications in various industries.

InChI:InChI=1/C5H4BrNOS/c6-3-4(8)5-7-1-2-9-5/h1-2H,3H2

Upstream product

• 24295-03-2 2-Acetylthiazole 
• 3034-53-5 2-bromo-1,3-thiazole 
• 105-36-2 ethyl bromoacetate 
• 15679-09-1 2-ethylthiazole 
• 40982-30-7 (±)-1-(thiazol-2-yl)ethanol 
• 288-47-1 1,3-thiazole 
• 96-32-2 bromoacetic acid methyl ester 
• 79265-30-8 2-(trimethylsilyl)thiazole 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 136029-16-8 ((2-thiazolylcarbonyl)methyl)triphenylphosphonium bromide 
• 736176-82-2 1-(4-phenylthiazol-2-yl)-4-(thiophen-2-yl)-1H-imidazol-2-amine 
• 1352450-34-0 (3R)-3-(2-(benzo[b]thiophen-2-yl)-2-(phenylamino)-acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane 2,2,2-trifluoroacetate 
• 1352450-23-7 (R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)-acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide 
• 1352450-63-5 (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide 
• 1352450-08-8 (3R)-3-(2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane trifluoroacetate 
• 1070143-75-7 1-(4-phenylthiazol-2-yl)-4-(thiazol-2-yl)-1H-imidazol-2-amine 
• 136029-15-7 1-(thiazol-2-yl)-2-(triphenyl-λ ⁵-phosphanylidene)ethan-1-one 
• 1233329-05-9 (R)-3-[2-(methyl-phenyl-amino)-2-phenyl-acetoxy]-1-(2-oxo-2-thiazol-2-ylethyl)-1-azonia-bicyclo[2.2.2]octane bromide 
• 1233329-10-6 (R)-3-(2-benzylamino-2-phenyl-acetoxy)-1-(2-oxo-2-thiazol-2-yl-ethyl)-1-azonia-bicyclo[2.2.2]octane ditrifluoroacetate 

Relevant academic research and scientific papers

Discovery of novel purinylthiazolylethanone derivatives as anti-Candida albicans agents through possible multifaceted mechanisms

An unprecedented amount of fungal and fungal-like infections has recently brought about some of the most severe die-offs and extinctions due to fungal drug resistance. Aimed to alleviate the situation, new effort was made to develop novel purinylthiazolylethanone derivatives, which were expected to combat the fungal drug resistance. Some prepared purinylthiazolylethanone derivatives possessed satisfactory inhibitory action towards the tested fungi, among which compound 8c gave a MIC value of 1 μg/mL against C. albicans. The active molecule 8c was able to kill C. albicans with undetectable resistance as well as low hematotoxicity and cytotoxicity. Furthermore, it could hinder the growth of C. albicans biofilm, thus avoiding the occurrence of drug resistance. Mechanism research manifested that purinylthiazolylethanone derivative 8c led to damage of cell wall and membrane disruption, so protein leakage and the cytoplasmic membrane depolarization were observed. On this account, the activity of fungal lactate dehydrogenase was reduced and metabolism was impeded. Meanwhile, the increased levels of reactive oxygen species (ROS) and reactive nitrogen species (RNS) disordered redox equilibrium, giving rise to oxidative damage to fungal cells and fungicidal effect.

Membrane active 7-thiazoxime quinolones as novel DNA binding agents to decrease the genes expression and exert potent anti-methicillin-resistant Staphylococcus aureus activity

A novel class of 7-thiazoxime quinolones was developed as potential antimicrobial agents for the sake of bypassing resistance of quinolones. Biological assays revealed that some constructed 7-thiazoxime quinolones possessed effective antibacterial efficiency. Methyl acetate oxime derivative 6l exhibited 32-fold more active than ciprofloxacin against MRSA, which also possessed rapidly bactericidal ability and low toxicity towards mammalian cells. The combination use of 7-thiazoxime quinolone 6l and ciprofloxacin was able to improve antibacterial potency and effectively alleviate bacterial resistance. The preliminarily mechanism exploration revealed that compound 6l could destroy the cell membrane and insert into MRSA DNA to bind with DNA gyrase, then decrease the expression of gyrB and femB genes. The above results strongly suggested that methyl acetate oxime derivative 6l held a promise for combating MRSA infection.

Novel chalcone-conjugated, multi-flexible end-group coumarin thiazole hybrids as potential antibacterial repressors against methicillin-resistant Staphylococcus aureus

The increasing resistance of methicillin-resistant Staphylococcus aureus (MRSA) to antibiotics has led to a growing effort to design and synthesize novel structural candidates of chalcone-conjugated, multi-flexible end-group coumarin thiazole hybrids with

Synthesis and Biological Evaluation of Quinazolonethiazoles as New Potential Conquerors towards Pseudomonas Aeruginosa

Novel quinazolonthiazoles were designed and synthesized as new potential antimicrobial agents by facile multi-step procedure from o-aminobenzoic acids and 2-acetylthiazole. A series of biological evaluation showed that compound 7d was the most effective quinazolonethiazole with superior activity to reference drugs chloramphenicol and norfloxacin. This active molecule displayed unobvious bacterial resistance against P. aeruginosa, the low toxicity to normal hepatocytes, suitable pharmacokinetics and drug-likeness. The preliminary biological interaction suggested that quinazolonethiazole 7d might induce bacterial death by disturbing the membrane permeability, whilst preventing bacteria from growth by integrating into DNA and binding with topoisomerase IV. These findings provided significant background for the further development of quinazolonethiazoles as new potential drugs in combating drug-resistant pathogens.

Identification of Unique Quinazolone Thiazoles as Novel Structural Scaffolds for Potential Gram-Negative Bacterial Conquerors

A class of quinazolone thiazoles was identified as new structural scaffolds for potential antibacterial conquerors to tackle dreadful resistance. Some prepared compounds exhibited favorable bacteriostatic efficiencies on tested bacteria, and the most representative 5j featuring the 4-trifluoromethylphenyl group possessed superior performances against Escherichia coli and Pseudomonas aeruginosa to norfloxacin. Further studies revealed that 5j with inappreciable hemolysis could hinder the formation of bacterial biofilms and trigger reactive oxygen species generation, which could take responsibility for emerging low resistance. Subsequent paralleled exploration discovered that 5j not only disintegrated outer and inner membranes to induce leakage of cytoplasmic contents but also broke the metabolism by suppressing dehydrogenase. Meanwhile, derivative 5j could intercalate into DNA to exert powerful antibacterial properties. Moreover, compound 5j gave synergistic effects against some Gram-negative bacteria in combination with norfloxacin. These findings indicated that this novel structural type of quinazolone thiazoles showed therapeutic foreground in struggling with Gram-negative bacterial infections.

Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents

(+)-Usnic acid, a product of secondary metabolism in lichens, has displayed a broad range of biological properties such as antitumor, antimicrobial, antiviral, anti-inflammatory, and insecticidal activities. Interested by these pharmacological activities and to tap into its potential, we herein present the synthesis and biological evaluation of new usnic acid enaminone-conjugated 1,2,3-triazoles 10-44 as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone 8 with a terminal ethynyl moiety. It was further reacted with various azides A1-A35 under copper catalysis to give triazoles 10-44 in good yields. Among the synthesized compounds, saccharin derivative 36 proved to be the most active analogue, inhibiting Mycobacterium tuberculosis (Mtb) at an MIC value of 2.5 μM. Analogues 16 and 27, with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on Bacillus subtilis, with compounds 18 [3-(trifluoromethyl)phenacyl] and 29 (N-acylmorpholinyl) showing inhibitory concentrations of 41 and 90.7 μM, respectively, while they were inactive on the other tested bacterial strains. Overall, the study presented here is useful for converting natural (+)-usnic acid into antitubercular and antibacterial agents via incorporation of enaminone and 1,2,3-triazole functionalities.

COMPOSITIONS AND METHODS OF MODULATING SHORT-CHAIN DEHYDROGENASE ACTIVITY

Compounds and methods of modulating 15-PGDH activity, modulating tissue prostaglandin levels, treating disease, diseases disorders, or conditions in which it is desired to modulate 15-PGDH activity and/or prostaglandin levels include 15-PGDH inhibitors described herein.

Ethoxy bridged thiazole coumarin compounds and preparation method and application thereof

The invention relates to ethoxy bridged thiazole coumarin compounds and a preparation method and application thereof, and belongs to the technical field of chemical synthesis. The general formula of the ethoxy bridged thiazole coumarin compounds is as sho

Quinazolone thiazole compounds, and preparation method and application thereof

The invention relates to quinazolone thiazole compounds, and a preparation method and an application thereof, and belongs to the technical field of chemical synthesis. The quinazolone thiazole compounds are represented by general formula I to IV. The compounds have a certain inhibitory activity to one or more of Gram-positive bacteria, Gram-negative bacteria and fungi, and can be used to prepare antibacterial and/or antifungal drugs in order to provide efficient and safe drug candidate drugs for clinical ant-microbial treatment and contribute to solve clinical treatment problems such as increasing drug resistance, stubborn pathogenic microorganisms and emerging harmful microorganisms.

Quinolone thiazoyloxime compounds, and preparation method and application thereof

The invention relates to quinolone thiazoyloxim compounds, and a preparation method and an application thereof, and belongs to the technical field of chemical synthesis. The quinolone thiazoyloxim compounds are represented by general formula I. The compou