299953-06-3

Basic information

• Product Name: 5-(4-methoxybenzyl)thiazol-2-amine
• Synonyms: 5-(4-methoxybenzyl)thiazol-2-amine;5-[(4-methoxyphenyl)methyl]-1,3-thiazol-2-amine
• CAS NO: 299953-06-3
• Molecular Formula: C₁₁H₁₂N₂OS
• Molecular Weight: 220
• Mol File: 299953-06-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 133-134 °C(Solv: chloroform (67-66-3); carbon tetrachloride (56-23-5))
• Boiling Point: 389.1±22.0 °C(Predicted)
• Appearance: /
• Density: 1.238±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 5.11±0.10(Predicted)
• CAS DataBase Reference: 5-(4-methoxybenzyl)thiazol-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-methoxybenzyl)thiazol-2-amine(299953-06-3)
• EPA Substance Registry System: 5-(4-methoxybenzyl)thiazol-2-amine(299953-06-3)

Safety Data

• Hazardous Substances Data: 299953-06-3(Hazardous Substances Data)

Usage

Description

5-(4-methoxybenzyl)thiazol-2-amine, also known as 5-[(4-Methoxyphenyl)methyl]-2-thiazolamine, is an organic compound with a thiazol-2-amine core structure. It is characterized by the presence of a 4-methoxybenzyl group attached to the 5th position of the thiazol ring. 5-(4-methoxybenzyl)thiazol-2-amine is of interest in the field of medicinal chemistry due to its potential applications in the development of therapeutic agents.

Uses

Used in Pharmaceutical Industry:
5-(4-methoxybenzyl)thiazol-2-amine is used as a reagent for the synthesis of 2-Amino-5-arylmethyl-1,3-thiazole derivatives. These derivatives have shown potential as therapeutic agents, particularly in the treatment of prostate cancer. 5-(4-methoxybenzyl)thiazol-2-amine plays a crucial role in the development of novel drugs that target specific pathways involved in cancer progression, making it a valuable asset in the fight against prostate cancer.

Upstream product

• 17356-08-0 thiourea 
• 807667-27-2 2-chloro-3-(4-methoxyphenyl)propanal 
• 4346-59-2 para-methoxyphenyldiazonium chloride 
• 100-66-3 methoxybenzene 
• 131184-73-1 (2-amino-1,3-thiazol-5-yl)methanol 
• 20401-88-1 3-(4-methoxyphenyl)propional 
• 915278-14-7 2-bromo-3-(4-methoxyphenyl)propanal 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 304895-28-1 N-[5-(4-methoxybenzyl)-1,3-thiazol-2-yl]heptanamide 
• 919018-21-6 N-[5-(4-methoxybenzyl)-1,3-thiazol-2-yl]chromane-3-carboxamide 
• 1384183-50-9 N-[5-(4-methoxy-benzyl)-thiazol-2-yl]-3-phenyl-propionamide 
• 304895-22-5 2-chloro-N-[5-[(4-methoxyphenyl)methyl]thiazol-2-yl]acetamide 

Relevant articles and documents

Synthesis and BK channel-opening activity of 2-amino-1,3-thiazole derivatives

A series of 2-amino-5-arylmethyl- or 5-heteroarylmethyl-1,3-thiazole derivatives were synthesized and evaluated for BK channel-opening activities in cell-based fluorescence assay and electrophysiological recording. The assay results indicated that the activities of the investigated compounds were influenced by the physicochemical properties of the substituent at benzene ring.

Aminothiazoles as Potent and Selective Sirt2 Inhibitors: A Structure-Activity Relationship Study

Sirtuins are NAD+-dependent protein deacylases that cleave off acetyl but also other acyl groups from the ε-amino group of lysines in histones and other substrate proteins. Dysregulation of human Sirt2 (hSirt2) activity has been associated with the pathogenesis of cancer, inflammation, and neurodegeneration, which makes the modulation of hSirt2 activity a promising strategy for pharmaceutical intervention. The sirtuin rearranging ligands (SirReals) have recently been discovered by us as highly potent and isotype-selective hSirt2 inhibitors. Here, we present a well-defined structure-activity relationship study, which rationalizes the unique features of the SirReals and probes the limits of modifications on this scaffold regarding inhibitor potency. Moreover, we present a crystal structure of hSirt2 in complex with an optimized SirReal derivative that exhibits an improved in vitro activity. Lastly, we show cellular hyperacetylation of the hSirt2 targeted tubulin caused by our improved lead structure.

Nucleophilic capture of the imino-quinone methide type intermediates generated from 2-aminothiazol-5-yl carbinols

Generation of imino-quinone methide type intermediates from 2-aminothiazole-5-carbinols using alkylsulfonic acids in nitromethane followed by trapping with a wide range of nucleophiles effects C-C, C-O, C-N, C-S, and C-P bond formation