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

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

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

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

Downstream Products

• 304895-28-1 N-[5-(4-methoxybenzyl)-1,3-thiazol-2-yl]heptanamide 
• 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 
• 919018-21-6 N-[5-(4-methoxybenzyl)-1,3-thiazol-2-yl]chromane-3-carboxamide 

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.

Synthesis and antitumor activities of new n-(5-benzylthiazol-2-yl)-2-(heteryl-5-ylsulfanyl)-acetamides

Aim. Synthesis of a series of new N-(5-benzyl-thiazol-2-yl)-2-(heteryl-5-ylsulfanyl)-acetamides and study of their anticancer activity. Methods. Organic synthesis, analytical and spectral methods, pharmacological screening. Results. [2-chloro-N-(5-aryl-1,

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.

NOVEL TUBULIN INHIBITORS AND METHODS OF USING THE SAME

Compounds represented by the formula (I) or pharmaceutically acceptable salts thereof: [in-line-formulae]R2—Y—Z-Q-A-R1??Formula (I)[/in-line-formulae] wherein R1, R2, Y, Z, Q, and A are as defined. These compoun

Discovery and potency optimization of 2-amino-5-arylmethyl-1,3-thiazole derivatives as potential therapeutic agents for prostate cancer

A new chemical series was identified via high-throughput screening as having antiproliferative activity on DU-145 human prostate carcinoma cell line (hit compound potency - 2.9 μM). Medicinal chemistry optimization of two peripheral diversity vectors of t

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

Heterocyclic syntheses on the basis of arylation products of unsaturated compounds: X. 3-aryl-2-chloropropanals as reagents for the synthesis of 2-amino-1,3-thiazole derivatives

Meerwein reaction of arenediazonium chlorides with acrolein gave 3-aryl-2-chloropropanals which were brought into cyclocondensation with thiourea. The resulting 2-amino-5-benzyl-1,3-thiazoles were acylated with carboxylic acid chlorides and phthalic anhydride to afford, respectively, 2-acylamino-5-benzyl-1,3-thiazoles and N-(5-benzyl-1,3-thiazol-2-yl) phthalimides.