312936-77-9

Basic information

• Product Name: 1-(4-BroMobenzyl)-2-Mercapto-5-hydroxyMethyliMidazole
• Synonyms: 1-(4-BroMobenzyl)-2-Mercapto-5-hydroxyMethyliMidazole;1-[(4-Bromophenyl)methyl]-1,3-dihydro-5-(hydroxymethyl)-2H-imidazole-2-thione
• CAS NO: 312936-77-9
• Molecular Formula: C₁₁H₁₁BrN₂OS
• Molecular Weight: 299.18684
• EINECS: -0
• Mol File: 312936-77-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-BroMobenzyl)-2-Mercapto-5-hydroxyMethyliMidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-BroMobenzyl)-2-Mercapto-5-hydroxyMethyliMidazole(312936-77-9)
• EPA Substance Registry System: 1-(4-BroMobenzyl)-2-Mercapto-5-hydroxyMethyliMidazole(312936-77-9)

Safety Data

• Hazardous Substances Data: 312936-77-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
1-(4-Bromobenzyl)-2-mercapto-5-hydroxymethylimidazole is used as a key compound in the development of drugs targeting the adenosine receptor for various therapeutic applications. Its unique structure allows for the modulation of adenosine receptor activity, which can lead to the development of new treatments for conditions such as asthma, chronic obstructive pulmonary disease (COPD), and other respiratory disorders.
Used in Research:
In the research industry, 1-(4-Bromobenzyl)-2-mercapto-5-hydroxymethylimidazole serves as a valuable tool for studying biochemical processes and the role of adenosine receptors in various physiological and pathological conditions. Its unique properties make it an essential component in the design and synthesis of novel compounds with potential therapeutic applications.
Used in Drug Development:
1-(4-Bromobenzyl)-2-mercapto-5-hydroxymethylimidazole is employed as a building block in the synthesis of new drug candidates targeting adenosine receptors. Its versatile structure enables the development of compounds with improved pharmacological properties, such as enhanced selectivity, potency, and bioavailability, which are crucial for the success of new therapeutic agents in the pharmaceutical industry.

Upstream product

• 62147-49-3 1,3-dihydroxyacetone dimer 
• 333-20-0 potassium thioacyanate 
• 26177-44-6 4-bromobenzylamine hydrochloride 
• 96-26-4 dihydroxyacetone 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 220364-22-7 1-(4-Bromobenzyl)-5-hydroxymethyl-1H-imidazole 
• 1417526-55-6 2-(hydroxymethyl)-1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole-5-carbaldehyde 
• 1432488-16-8 C₃₃H₃₉F₃N₆OS 
• 1417526-61-4 ethyl 1-(4-bromobenzyl)-1H-imidazole-5-carboxylate 

Relevant articles and documents

Triazole derivatives: A series of Darapladib analogues as orally active Lp-PLA2 inhibitors

This Letter reports our efforts towards the optimization of our previously identified series of imidazole and triazole derivatives that lead to the discovery of a series of orally active Lp-PLA2 inhibitors in C57 mice. These inhibitors are characterized by the presence of a diamine side chain in the molecules, such as 2c, 2f, and 4a. The introduction of the terminal-end amine succeeded in maintaining the in vitro activities at sub-nanomolar levels. The vivo activities could be greatly affected by variations in the two amines via modulating the metabolic stability and lipophilicity of the compounds.

Preparation of a clinically investigated ras farnesyl transferase inhibitor

The synthesis of ras farnesyl-protein transferase inhibitor 1 is described on a multi-kilogram scale. Retrosynthetic analysis reveals chloromethylimidazole 2 and a piperazinone 3 as viable precursors. The 1,5-disubstituted imidazole system was regioselectively assembled via an improved Marckwald imidazole synthesis. A new imidazole dethionation procedure has been developed to convert the Marckwald mercaptoimidazole product to the desired imidazole. This methodology was found to be tolerant of a variety of functional groups providing good to excellent yields of 1,5-disubstituted imidazoles. A new Mitsunobu cyclization strategy was developed to prepare the arylpiperazinone fragment 3.

Process for making 1,5-disubstituted imidazoles

The present invention is directed to a process for synthesizing 1,5-disubstituted imidazoles, which are useful in the preparation of farnesyl-protein transferase inhibitors.