7520-94-7

Usage

Uses

Used in Pharmaceutical Research and Development:
1-(4-METHYL-2-PHENYL-1,3-THIAZOL-5-YL)ETHAN-1-ONE is used as a compound in pharmaceutical research and development for its demonstrated biological activities. 1-(4-METHYL-2-PHENYL-1,3-THIAZOL-5-YL)ETHAN-1-ONE's antimicrobial, antifungal, and antitumor properties make it a promising candidate for the creation of new drugs and therapies.
Used in Antimicrobial Applications:
In the field of antimicrobials, 1-(4-METHYL-2-PHENYL-1,3-THIAZOL-5-YL)ETHAN-1-ONE is used as an active ingredient to combat various types of bacteria and other microorganisms, potentially leading to the development of new antibiotics.
Used in Antifungal Applications:
1-(4-METHYL-2-PHENYL-1,3-THIAZOL-5-YL)ETHAN-1-ONE is utilized as an antifungal agent, targeting and inhibiting the growth of fungi, which can be applied in the treatment of various fungal infections.
Used in Antitumor Applications:
Within the context of antitumor applications, 1-(4-METHYL-2-PHENYL-1,3-THIAZOL-5-YL)ETHAN-1-ONE is used as a compound with potential antitumor properties, possibly contributing to the development of novel cancer treatments.
Used in Other Industries:
1-(4-METHYL-2-PHENYL-1,3-THIAZOL-5-YL)ETHAN-1-ONE may also be employed in various other industries that benefit from the use of thiazole derivatives, such as the chemical, material science, and agricultural sectors, for a range of applications including the development of new products and enhancement of existing ones.

InChI:InChI=1/C12H11NOS/c1-8-11(9(2)14)15-12(13-8)10-6-4-3-5-7-10/h3-7H,1-2H3

Upstream product

• 54001-24-0 2-diazo-1-(4-methyl-2-phenyl-thiazol-5-yl)-ethanone 
• 1694-29-7 3-chloropentane-2,4-dione 
• 2227-79-4 benzenecarbothioamide 
• 2227-79-4 phenylthioamide 
• 72997-31-0 HacacBr 
• 3043-28-5 3-bromopentane-2,4-dione 
• 100288-98-0 <1-Hydroxy-1-(4-methyl-2-phenyl-5-thiazolyl)ethyl>phosphonsaeure-diethylester 
• 98732-74-2 E-1-Methyl-3-oxo-1-butenylphosphonsaeurediethylester 
• 33763-20-1 4-methyl-2-(phenyl)-1,3-thiazol-5-carboxylic acid 
• 53715-64-3 4-methyl-2-phenyl-thiazole-5-carboxylic acid ethyl ester 
• 81447-35-0 2,4-dioxopentan-3-yl 4-methylbenzenesulfonate 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 55-21-0 benzamide 

Downstream Products

• 54001-08-0 1-[4-methyl-2-(4-nitro-phenyl)-thiazol-5-yl]-ethanone 
• 122229-20-3 2,2-Dimethoxy-2-(4-methyl-2-phenyl-thiazol-5-yl)-ethanol 
• 7520-95-8 2-bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone 
• 123888-44-8 Methyl 4-Bromomethyl-2-phenyl-5-thiazolyl Ketone 
• 80269-16-5 2-Phenyl-4-methyl-5-glyoxyloyl-thiazol 
• 243665-60-3 1-[2'-phenyl-4'-methylthiazol-5'-yl]-3-(4'-methoxyphenyl)-2-propen-1-one 
• 257862-98-9 3-(dimethylamino)-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)prop-2-ene-1-one 
• 1537168-34-5 2-[1-(4-methyl-2-phenylthiazol-5-yl)ethylidene]hydrazinecarboximidamide 
• 61108-35-8 4′-methyl-N,2′-diphenyl-4,5′-bisthiazol-2-amine 

Relevant academic research and scientific papers

Dependence on the Pyrimidine Biosynthetic Enzyme DHODH Is a Synthetic Lethal Vulnerability in Mutant KRAS-Driven Cancers

Activating KRAS mutations are major oncogenic drivers in multiple tumor types. Synthetic lethal screens have previously been used to identify targets critical for the survival of KRAS mutant cells, but their application to drug discovery has proven challenging, possibly due in part to a failure of monolayer cultures to model tumor biology. Here, we report the results of a high-throughput synthetic lethal screen for small molecules that selectively inhibit the growth of KRAS mutant cell lines in soft agar. Chemoproteomic profiling identifies the target of the most KRAS-selective chemical series as dihydroorotate dehydrogenase (DHODH). DHODH inhibition is shown to perturb multiple metabolic pathways. In vivo preclinical studies demonstrate strong antitumor activity upon DHODH inhibition in a pancreatic tumor xenograft model. Koundinya et al. show that inhibitors of the pyrimidine biosynthetic enzyme dihydroorotate dehydrogenase selectively inhibit the growth of KRAS mutant cell lines. Differential sensitivity of the mutant lines correlates with differential effects of the inhibitors on primary energy metabolism and glutamine levels, and the inhibitors synergize with some clinically used anticancer agents.

An efficient, one-pot, regioselective synthesis of 2-aryl/hetaryl-4-methyl-5-acylthiazoles under solvent-free conditions

In this article, we present an efficient, one-pot regioselective approach towards the synthesis of 2-aryl/hetaryl-4-methyl-5-acylthiazoles obtained during the reaction of α-bromo-1,3-diketones generated in situ by triturating unsymmetrical 1,3-diketones with N-bromosuccinimide, with various thioamides under solvent-free conditions. This environmentally benign protocol showed large functional group tolerance, resulted in the exclusive formation of a single isomer, out of the two possible regioisomers in admirable yields. The structure of the isomeric thiazole was assigned unambiguously on the basis of multinuclear NMR [(1H-13C) HMBC, (1H-13C) HMQC, (1H-15N) HMBC] and X-ray crystallographic studies. The entire protocol is ecologically desirable as it employs no organic solvent.

Novel cyanothiouracil and cyanothiocytosine derivatives as concentration-dependent selective inhibitors of U87MG glioblastomas: Adenosine receptor binding and potent PDE4 inhibition

Thiouracil and thiocytosine are important heterocyclic pharmacophores having pharmacological diversity. Antitumor and antiviral activity is commonly associated with thiouracil and thiocytosine derivatives, which are well known fragments for adenosine receptor affinity with many associated pharmacological properties. In this respect, 33 novel compounds have been synthesized in two groups: 24 thiouracil derivatives (4a-x) and 9 thiocytosine derivatives (5a-i). Antitumor activity of all the compounds was determined in the U87 MG glioblastoma cell line. Compound 5e showed an anti-proliferative IC50 of 1.56 μM, which is slightly higher activity than cisplatin (1.67 μM). The 11 most active compounds showed no signficant binding to adenosine A1, A2A or A2B receptors at 1 μM. Brain tumors express high amounts of phosphodiesterases. Compounds were tested for PDE4 inhibition, and 5e and 5f showed the best potency (5e: 3.42 μM; 5f: 0.97 μM). Remakably, those compounds were also the most active against U87MG. However, the compounds lacked a cytotoxic effect on the HEK293 healthy cell line, which encourages further investigation.

Versatile approaches to a library of building blocks based on 5-acylthiazole skeleton

Thiazole derivatives represent an important class of azole heterocycles with a broad spectrum of biological activity and, therefore, the synthesis of these compounds is of remarkable concern. We present here practical and reliable protocol for synthesis of some 5-acylthiazoles and demonstrate their utility in the preparation of several new series of thiazole-containing building blocks through transformation of 5-acyl function. Specifically, thiazole-based alcohols, oximes, primary, and secondary amines were successively synthesized in good to excellent yields. The chemical structures of obtained compounds were confirmed by 1H and 13C NMR-spectroscopy, elemental analysis, and mass-spectrometry.

Potent ribonucleotide reductase inhibitors: Thiazole-containing thiosemicarbazone derivatives

The antioxidant, antimalarial, antibacterial, and antitumor activities of thiosemicarbazones have made this class of compounds important for medicinal chemists. In addition, thiosemicarbazones are among the most potent and well-known ribonucleotide reductase inhibitors. In this study, 24 new thiosemicarbazone derivatives were synthesized, and the structures and purity of the compounds were determined by IR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis. The IC50 values of these 24 compounds were determined with an assay for ribonucleotide reductase inhibition. Compounds 19, 20, and 24 inhibited ribonucleotide reductase enzyme activity at a higher level than metisazone as standard. The cytotoxic effects of these compounds were measured on the MCF7 (human breast adenocarcinoma) and HEK293 (human embryonic kidney) cell lines. Similarly, compounds 19, 20, and 24 had a selective effect on the MCF7 and HEK293 cell lines, killing more cancer cells than cisplatin as standard. The compounds (especially 19, 20, and 24 as the most active ones) were then subjected to docking experiments to identify the probable interactions between the ligands and the enzyme active site. The complex formation was shown qualitatively. The ADME (absorption, distribution, metabolism, and excretion) properties of the compounds were analyzed using in-silico techniques.

Synthesis, Characterization, and Antimicrobial Screening of 4″-methyl-2,2″-diaryl-4,2′:4′,5″-terthiazole Derivatives

A series of novel 4″-methyl-2,2″-diaryl-4,2′:4′,5″-terthiazole (8a-p) derivatives has been synthesized and screened for antibacterial activity against four pathogenic bacteria, Escherichia coli, Pseudomonas flurescence, Staphylococcus aureus, and Bacillus subtilis. Among them, compounds 8a and 8j exhibited excellent antibacterial activity with minimum inhibitory concentration range of 1.0 to 5.3?μg/mL and compounds 8m and 8p exhibited moderate to good antibacterial activity with minimum inhibitory concentration range of 16.9 to 29.7?μg/mL against all tested strains. All the synthesized compounds were screened for their in vitro antifungal activity against Cocinida candida. Most of the compounds reported moderate antifungal activity. This study provides valuable directions to our ongoing endeavor of rationally designing more potent antimicrobial agent.

Synthesis, antitubercular and antimicrobial potential of some new thiazole substituted thiosemicarbazide derivatives

The increase in antibiotic resistance due to multiple factors has warranted the need for search of new compounds which are active against multidrug resistant pathogens. In this context a small focused library of thiosemicarbazide derivatives of 2-arylthiazole-4-carbaldehyde, 4-methyl-2-arylthiazole-5-carbaldehyde and 1-(4-methyl-2-arylthiazol-5-yl) ethanone, (5a–l) has been synthesized. The title compounds were screened for inhibitory activity against Mycobacterium tuberculosis H37Ra (ATCC 25177) and Mycobacterium bovis Bacille Calmette Guerin (ATCC 35743) strains. The synthesized compounds, 5a–l were further assayed for their cytotoxic activity against the two human cancer cell lines, HeLa and human colon carcinoma 116 cell lines and showed no significant cytotoxic activity against these two cell lines at the maximum concentration evaluated. Further, the synthesized compounds were found to have potential antibacterial activity against Gram-negative bacteria, Escherichia coli, Pseudomonas flurescence and Gram-positive bacteria, Staphylococcus aureus, Bacillus subtilis. Most of the synthesized compounds showed moderate activity against fungal strain Candida albicans. This study provides valuable directions to our ongoing endeavor of rationally designing more potent antimycobacterial agent.

Fused Heterocycles: Synthesis and Antitubercular Activity of Novel 6-Substituted-2-(4-methyl-2-substituted phenylthiazol-5-yl)H-imidazo[1,2-a]pyridine

(Chemical Equation Presented) A series of 6-substituted-2-(4-methyl-2-substituted phenylthiazol-5-yl)H-imidazo[1,2-a]pyridine derivatives 4a-4l is described. The antitubercular activity of the synthesized compounds was determined against Mycobacterium smegmatis MC2 155 strain. From the activity result, it was found that the phenyl or 4-fluorophenyl group at 2 position of thiazole nucleus and bromo substituent at 6 position of imidazo[1,2-a]pyridine showed good antitubercular activity.

Synthesis and biological screening of 2′-aryl/benzyl-2-aryl-4-methyl-4′,5-bithiazolyls as possible anti-tubercular and antimicrobial agents

A series of 2′-aryl/benzyl-2-aryl-4-methyl-4′,5-bithiazolyl derivatives, 25-64 were synthesized and evaluated for inhibitory activity against Mycobacterium smegmatis MC2 155 strain and antimicrobial activities against four pathogenic bacteria Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Proteus vulgaris. Among them, compounds 40, 49, 50, and 54 exhibited moderate to good inhibition on the growth of the bacteria Mycobacterium smegmatis at the concentration of 30 μM. Compounds 26, 40, 44, 54 and 56 exhibited moderate to good antibacterial activity. Compound 5-(2′-(4-fluorobenzyl)thiazol-4′-yl)-2-(4-fluorophenyl)-4-methyl-thiazole (54) exhibited both antitubercular as well as antimicrobial activity against all tested strains.

Synthesis and Antimicrobial Evaluation of Some New 4,5′-Bisthiazoles

Thiazole and bisthiazole derivatives represent a prevalent scaffold in the antimicrobial drug discovery. Therefore, we have decided to synthesize some new series of 4,5′-bisthiazoles. A total of 17 compounds were synthesized, their structural elucidation