93209-95-1

Basic information

• Product Name: 4-(2-METHOXY-PHENYL)-THIAZOL-2-YLAMINE
• Synonyms: TIMTEC-BB SBB011148;ASINEX-REAG BAS 12365880;AKOS BBS-00008014;4-(2-METHOXY-PHENYL)-THIAZOL-2-YLAMINE;4-(2-Methoxyphenyl)thiazol-2-amine
• CAS NO: 93209-95-1
• Molecular Formula: C₁₀H₁₀N₂OS
• Molecular Weight: 206.26
• Mol File: 93209-95-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(2-METHOXY-PHENYL)-THIAZOL-2-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-METHOXY-PHENYL)-THIAZOL-2-YLAMINE(93209-95-1)
• EPA Substance Registry System: 4-(2-METHOXY-PHENYL)-THIAZOL-2-YLAMINE(93209-95-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 93209-95-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-Methoxy-phenyl)-thiazol-2-ylamine is used as a pharmaceutical candidate for its potential antimicrobial, antifungal, and anticancer properties. The presence of the thiazol-2-ylamine core and the 2-methoxyphenyl group may contribute to its effectiveness in treating various diseases and conditions.
Used in Antimicrobial Applications:
In the field of antimicrobial research, 4-(2-Methoxy-phenyl)-thiazol-2-ylamine is used as an agent to combat microbial infections. Its thiazole derivative nature suggests it may have broad-spectrum antimicrobial activity, which could be beneficial in treating a range of bacterial and fungal infections.
Used in Antifungal Applications:
4-(2-Methoxy-phenyl)-thiazol-2-ylamine is also used as an antifungal agent, leveraging its thiazole structure to target and inhibit fungal growth. This makes it a potential candidate for developing treatments for various fungal infections.
Used in Anticancer Applications:
As an anticancer agent, 4-(2-Methoxy-phenyl)-thiazol-2-ylamine is used to target and inhibit the growth of cancer cells. Its potential to interfere with cancer-related biological processes makes it a promising compound for further research and development in oncology.
Further research is necessary to fully understand the extent of 4-(2-Methoxy-phenyl)-thiazol-2-ylamine's potential applications and to optimize its use in various industries.

Upstream product

• 31949-21-0 bromomethyl 2-methoxyphenyl ketone 
• 333-20-0 potassium thioacyanate 
• 7169-17-7 2-diazo-1-(2-methoxyphenyl)ethanone 
• 17356-08-0 thiourea 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 579-74-8 2-Methoxyacetophenone 

Downstream Products

• 74604-38-9 N-[4-(2-Methoxy-phenyl)-thiazol-2-yl]-oxalamic acid ethyl ester 
• 1446148-29-3 C₁₈H₁₆N₂O₂S 
• 1446148-30-6 C₁₈H₁₆N₂O₂S 
• 1446148-31-7 C₁₈H₁₆N₂O₂S 
• 1446148-32-8 C₁₈H₁₆N₂O₃S 
• 1446148-33-9 C₁₇H₁₃BrN₂O₂S 
• 1446148-34-0 C₂₁H₁₆N₂O₂S 
• 1449016-05-0 N-[4-(o-methoxyphenyl)-1,3-thiazol-2-yl]-2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamide 

Relevant articles and documents

A 4-(o-methoxyphenyl)-2-aminothiazole: An anti-quorum sensing compound

The 4-(o-methoxyphenyl)-2 aminothiazole was synthesized by reacting o-methoxyacetophenone, iodine, and thiourea; and characterized by spectral UV-Visible, Infra-Red (IR), H1 nuclear magnetic resonance, C 13NMR, gas chromatography-mas

Structure-Based Design of N-(5-Phenylthiazol-2-yl)acrylamides as Novel and Potent Glutathione S-Transferase Omega 1 Inhibitors

Using reported glutathione S-transferase omega 1 (GSTO1-1) cocrystal structures, we designed and synthesized acrylamide-containing compounds that covalently bind to Cys32 on the catalytic site. Starting from a thiazole derivative 10 (GSTO1-1 IC50 = 0.6 μM), compound 18 was synthesized and cocrystallized with GSTO1. Modification on the amide moiety of hit compound 10 significantly increased the GSTO1-1 inhibitory potency. We solved the cocrystal structures of new derivatives, 37 and 44, bearing an amide side chain bound to GSTO1. These new structures showed a reorientation of the phenyl thiazole core of inhibitors, 37 and 44, when compared to 18. Guided by the cocrystal structure of GSTO1:44, analogue 49 was designed, resulting in the most potent GSTO1-1 inhibitor (IC50 = 0.22 ± 0.02 nM) known to date. We believe that our data will form the basis for future studies of developing GSTO1-1 as a new drug target for cancer therapy.

Novel 1,3,5-triazine derivatives exert potent anti-cervical cancer effects by modulating Bax, Bcl2 and Caspases expression

This study aimed to develop novel 1,3,5-triazine derivatives as potent anti-cervical cancer agents. The compounds were synthesized in short steps with an excellent yield and characterized via various spectroscopic and analytical methods. A structure–activity relationship study suggested that electron-withdrawing substituents showed greater anticancer activity than electron-donating groups. Compound 7p (p-fluoro) showed the highest activity against cervical cancer cells. In a nude mouse xenograft model inoculated with HeLa cells, 7p showed dose-dependent inhibition of cervical tumour growth. Histopathological examination of excised tumour-bearing tissues showed that 7p improved the microstructure in a dose-dependent manner. Compound 7p also increased the proportions of HeLa cells in G0/G1 and S-phase and significantly decreased that of G2/M-phase. The effects of 7p on C-caspase-3, C-caspase-9, Bcl-2 and Bax expression in HeLa cells were also determined.

An efficient PEG-400 mediated catalyst free green synthesis of 2-amino-thiazoles from α-diazoketones and thiourea

A simple and efficient method has been developed for the synthesis of 2-aminothiazoles from α-diazoketones using PEG-400 solvent system. This novel synthetic approach involves the reaction between thiourea and α-diazoketones in PEG-400 at 100 °C to yield the corresponding 2-aminothiazoles in good yields. The method is simple, rapid and generates thiazole derivatives in excellent yields without the use of any catalysts. This green protocol can be utilized for fast synthesis of various 2-aminothiazoles in good yields. [Figure not available: see fulltext.]

Identification of novel 2-aminothiazole conjugated nitrofuran as antitubercular and antibacterial agents

The emergence of antibiotic resistant pathogens is an ongoing main problem in the therapy of bacterial infections. In order to develop promising antitubercular and antibacterial lead compounds, we designed and synthesized a new series of derivatives of 2-aminothiazole conjugated nitrofuran with activities against both Mycobacterium tuberculosis and Staphylococcus aureus. Eight compounds 12e, 12k, 12l, 12m, 18a, 18d, 18e, and 18j emerged as promising antitubercular agents. Structure–activity relationships (SARs) were discussed and showed that the derivatives substituted at the position-3 of benzene of 5-nitro-N-(4-phenylthiazol-2-yl)furan-2-carboxamide exhibited superior potency. The most potent compound 18e, substituted with benzamide at this position, displayed minimum inhibitory concentrations (MICs) of 0.27 μg/mL against Mtb H37Ra and 1.36 μg/mL against S. aureus. Furthermore, compound 18e had no obvious cytotoxicity to normal Vero cells (IC50= 50.2 μM). The results suggest that the novel scaffolds of aminothiazole conjugated nitrofuran would be a promising class of potent antitubercular and antimicrobial agents.

Carbon tetrabromide mediated oxidative cyclocondensation of ketones and thioureas: An easy access to 2-aminothiazoles

A simple, mild, and efficient one-pot method for the synthesis of substituted 2-aminothiazoles has been reported. The reaction involves the formation of sulfenyl bromide as an umpolung intermediate of nucleophilic sulfur, which is responsible for C-S bond formation leading to oxidative cyclization of ketones and thioureas to furnish the desired products. Carbon tetrabromide was used as a convenient and mild brominating reagent under basic condition at room temperature to give 2-aminothiazoles in good to excellent yields.

Synthesis and biological evaluation of N-(4-phenylthiazol-2-yl)cinnamamide derivatives as novel potential anti-tumor agents

In this study, a series of novel N-(4-phenylthiazol-2-yl)cinnamamide derivatives (7a-8n) were synthesized and evaluated for their anti-proliferative activities in vitro by MTT assay and a possible antitumor mechanism was also explored. SAR analysis showed that steric effects played an important role on the anti-tumor activity. The most potent analogue 8f showed excellent inhibitions on the K562, Bel7402, A549 and Jurkat cells ranging from sub-micromolar to nanomolar concentration. Compound 8f inhibited Jurkat cells with an IC50 value of 0.035 μM with no apparent toxicity in different non-cancerous cells. Furthermore, it was suggested that the possible mechanism of 8f might be associated with inducing cancer cell apoptosis following flow cytometer analysis and Hoechst 33358 staining assays.

Synthesis and anticancer evaluation of 3-aryl-6-phenylimidazo[2,1-b]thiazoles

A series of new 3,6-diphenylimidazo[2,1-b]thiazole derivatives (4a-l) are synthesized and evaluated for their anticancer activity. Some of the synthesized compounds have shown potent anti-proliferative activity against HeLa, MDA-MB-231, A549 and THP1 huma

Novel 2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamides as antioxidant and/or anti-inflammatory compounds

A series of novel N-(4-aryl-1,3-thiazol-2-yl)-2-(2,4-dioxo-1,3-thiazolidin- 5-yl)acetamides (4a-k) and N-(1,3-benzothiazol-2-yl)-2-(2,4-dioxo-1,3- thiazolidin-5-yl)acetamide derivatives (4l-o) are synthesized and evaluated for their anti-inflammatory and antioxidant activity (DPPH radical scavenging, superoxide anion scavenging, lipid peroxide inhibition, erythrocyte hemolytic inhibition). Compounds 4k and 4l have exhibited good antioxidant activity in four assays, while compounds 4c, 4d , 4m, 4n and 4o have shown good DPPH radical scavenging efficacy. Compounds 4a, 4h , 4i, 4k, 4m and 4n have possessed excellent anti-inflammatory activity. N-[4-(o-methoxyphenyl)-1,3-thiazol-2-yl]- 2-(2,4-dioxo-1,3-thiazolidin-5-yl) acetamide (4k) and N-(6-nitro-/methoxy-1,3- benzothiazol-2-yl)-2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamide (4m and 4n) have exhibited both antioxidant and anti-inflammatory activities.

First example of the coupling of α-diazoketones with thiourea: a novel route for the synthesis of 2-aminothiazoles

α-Diazoketones undergo smooth coupling with thiourea in the presence of 10 mol % of copper(II) triflate to produce the corresponding 2-aminothiazoles in excellent yields with high selectivity. The use of copper(II) triflate makes this method simple, convenient and practical. This method works well with both aryl and alkyl diazoketones to furnish a wide range of 2-aminothiazoles.