24827-38-1

Basic information

• Product Name: 4,5-BIS-(4-METHOXY-PHENYL)-THIAZOL-2-YLAMINE
• Synonyms: bis(4-Methoxyphenyl)-1,3-thiazol-2-aMine
• CAS NO: 24827-38-1
• Molecular Formula: C₁₇H₁₆N₂O₂S
• Molecular Weight: 312.3861
• Mol File: 24827-38-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 482.1 °C at 760mmHg
• Flash Point: 245.3 °C
• Appearance: /
• Density: 1.234 g/cm³
• Vapor Pressure: 1.89E-09mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: 4,5-BIS-(4-METHOXY-PHENYL)-THIAZOL-2-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-BIS-(4-METHOXY-PHENYL)-THIAZOL-2-YLAMINE(24827-38-1)
• EPA Substance Registry System: 4,5-BIS-(4-METHOXY-PHENYL)-THIAZOL-2-YLAMINE(24827-38-1)

Safety Data

• Hazardous Substances Data: 24827-38-1(Hazardous Substances Data)

Usage

General Description

4,5-BIS-(4-METHOXY-PHENYL)-THIAZOL-2-YLAMINE is a chemical compound with a molecular formula of C18H16N2O2S and a molecular weight of 324.4 g/mol. It is a thiazole derivative with two 4-methoxy-phenyl groups attached to the thiazole ring. 4,5-BIS-(4-METHOXY-PHENYL)-THIAZOL-2-YLAMINE is used in research and development as a building block for the synthesis of various other organic compounds. Its chemical structure and properties make it a useful intermediate in the production of pharmaceuticals and agrochemicals. Additionally, its thiazole ring structure suggests potential biological activity, and it may have applications in the development of new drugs or as a potential lead compound in drug discovery.

InChI:InChI=1/C17H16N2O2S/c1-20-13-7-3-11(4-8-13)15-16(22-17(18)19-15)12-5-9-14(21-2)10-6-12/h3-10H,1-2H3,(H2,18,19)

Upstream product

• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 
• 17356-08-0 thiourea 
• 123-11-5 4-methoxy-benzaldehyde 
• 119-52-8 4,4'-dimethoxybenzoin 
• 71193-36-7 (α-chloro-4-methoxybenzyl)-(4-methoxyphenyl)-ketone 
• 27895-95-0 2-bromo-1,2-bis(4-methoxyphenyl)ethanone 

Downstream Products

• 105197-04-4 [4,5-Bis-(4-methoxy-phenyl)-thiazol-2-yl]-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amine 
• 105197-03-3 2-{[(E)-4,5-Bis-(4-methoxy-phenyl)-thiazol-2-ylimino]-methyl}-phenol 

Relevant articles and documents

Design and synthesis of imidazo[2,1-b]thiazole-chalcone conjugates: Microtubule-destabilizing agents

A series of chalcone conjugates featuring the imidazo[2,1- b]thiazole scaffold was designed, synthesized, and evaluated for their cytotoxic activity against five human cancer cell lines (MCF-7, A549, HeLa, DU-145 and HT-29). These new hybrid molecules have shown promising cytotoxic activity with IC50 values ranging from 0.64 to 30.9 mm. Among them, (E)-3-(6-(4- fluorophenyl)-2,3-bis(4-methoxyphenyl)imidazo[2,1-b]thiazol-5- yl)-1-(pyridin-2-yl)prop-2-en-1-one (11 x) showed potent antiproliferative activity with IC50 values ranging from 0.64 to 1.44 mm in all tested cell lines. To investigate the mechanism of action, the detailed biological aspects of this promising conjugate (11x) were carried out on the A549 lung cancer cell line. The tubulin polymerization assay and immunofluoresence analysis results suggest that this conjugate effectively inhibits microtubule assembly in A549 cells. Flow cytometric analysis revealed that this conjugate induces cell-cycle arrest in the G2/M phase and leads to apoptotic cell death. This was further confirmed by Hoechst staining, activation of caspase-3, DNA fragmentation analysis, and Annexin V-FITC assay. Moreover, molecular docking studies indicated that this conjugate (11 x) interacts and binds efficiently with the tubulin protein.

Design, synthesis and analgesic/anti-inflammatory evaluation of novel diarylthiazole and diarylimidazole derivatives towards selective COX-1 inhibitors with better gastric profile

The inhibition of gastric cyclooxygenase 1 (COX-1) enzyme was believed to be the major cause of non-steroidal anti-inflammatory drugs (NSAIDs)-induced gastric ulcer. Recent studies disproved this belief and showed that the gastric tissues vulnerability is not solely connected to COX-1 inhibition. This work aimed at exploring and rationalizing the differential analgesic and anti-inflammatory activities of novel selective COX-1 inhibitors with improved gastric profile. Two novel series of 4,5-diarylthiazole and diarylimidazole were designed, synthesized in analogy to selective COX-1 inhibitors (mofezolac and FR122047) which lack gastric damaging effects. The new compounds were evaluated in vitro for their COXs inhibitory activity and in vivo for their anti-inflammatory and analgesic potentials. Four compounds; diphenylthiazole glycine derivatives (15a, 15b) and diphenylimidazolo acetic acid derivatives (19a, 19b), which possess carboxylic acid group exhibited significant activity and selectivity against COX-1 over COX-2. Of these compounds, (4,5-bis(4-methoxyphenyl)thiazol-2-yl)glycine 15b was the most potent compound against COX-1 with an inhibitory half maximal concentration (IC50) of 0.32 μM and a selectivity index (COX-2 IC50/COX-1 IC50) of 28.84. Furthermore, an ulcerogenicity study was performed where the tested compounds demonstrated a significant gastric tolerance. Interestingly, the most selective COX-1 inhibitor showed higher analgesic activity in vivo as expected compared to their moderate anti-inflammatory activity. This study underscores the need for further design and development of novel analgesic agents with low tendency to cause gastric damage based on improving their COX-1 affinity and selectivity profile.

Synthesis of some Thiazole Schiff Bases and Their Derivatives

Synthesis of some Schiff bases derived from 4,5-diaryl-2-aminothiazoles have been described.Cycloaddition of the Schiff bases with thioglycolic acid gave the corresponding thiazolidone derivatives.Reaction with cyclohexanone gave the secondary amines.The compounds have been characterised by ir and mass spectra, and screened for antifungal activity.