442-52-4

Basic information

• Product Name: Clemizole
• Synonyms: 1-p-Chlorobenzyl-2-[1-pyrrolidinylmethyl] benzimidazole;1-(p-Chlorobenzyl)-2-pyrrolidylmethylenebenzimidazole;1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-1H-benzimidazole (Clemizole);1-(4-Chlorobenzyl)-2-(pyrrolizinomethyl)-1H-benzimidazole;1-(p-Chlorobenzyl)-2-(1-pyrrolidinylmethyl)-1H-benzimidazole;Histacur;1-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)benzimidazole;1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole
• CAS NO: 442-52-4
• Molecular Formula: C₁₉H₂₀ClN₃
• Molecular Weight: 325.8352
• EINECS: 207-133-5
• Product Categories: API intermediates;Inhibitors
• Mol File: 442-52-4.mol

Chemical Properties

• Melting Point: 239-241℃
• Boiling Point: 506.1°Cat760mmHg
• Flash Point: 259.9°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 2.29E-10mmHg at 25°C
• Refractive Index: 1.655
• Solubility: insoluble in H2O; ≥16.2 mg/mL in DMSO; ≥95.8 mg/mL in EtOH
• CAS DataBase Reference: Clemizole(CAS DataBase Reference)
• NIST Chemistry Reference: Clemizole(442-52-4)
• EPA Substance Registry System: Clemizole(442-52-4)

Safety Data

• Hazardous Substances Data: 442-52-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Clemizole is used as a pharmaceutical agent for its potential therapeutic effects. Its benzimidazole structure allows it to interact with various biological targets, making it a candidate for the development of drugs to treat specific conditions.
Used in Chemical Research:
In the field of chemical research, Clemizole serves as a valuable compound for studying the properties and reactions of benzimidazole derivatives. Its unique substitution pattern can provide insights into the synthesis and modification of related compounds for various applications.
Used in Material Science:
Clemizole's molecular structure may also find applications in material science, where its specific interactions with other molecules could be harnessed to develop new materials with tailored properties for use in various industries.

Therapeutic Function

Antihistaminic

Biological Activity

the ns4b protein is a key player in hcv replication. disrupting ns4b function thus represents an attractive new anti-hcv strategy. combining clemizole with other anti-hcv agents could increase the antiviral effect achieved with 1 active drug alone and decrease emergence of viral resistance.

in vivo

clemizole had an unexpectedly short plasma half-life; it was very rapidly biotransformed into a glucuronide (m14) and a dealkylated metabolite (m12) and into a variety of lesser metabolites in c57bl/6j mice [2].

InChI:InChI=1/C19H20ClN3/c20-16-9-7-15(8-10-16)13-23-18-6-2-1-5-17(18)21-19(23)14-22-11-3-4-12-22/h1-2,5-10H,3-4,11-14H2

Upstream product

• 123-75-1 pyrrolidine 
• 101103-28-0 chloro-acetic acid-[2-(4-chloro-benzylamino)-anilide] 
• 7189-18-6 1-(4-chlorobenzyl)-2-(chloromethyl)-1H-benzo[d]imidazole 
• 109037-60-7 pyrrolidino-acetic acid-[2-(4-chloro-benzylidenamino)-anilide] 
• 718634-79-8 pyrrolidino-acetic acid-[2-(4-chloro-benzylamino)-anilide] 
• 622-95-7 4-chlorobenzyl bromide 
• 5822-16-2 N-(p-Chlorobenzyl)-2-nitro aniline 
• 5729-18-0 N-(p-Chlorophenylmethyl)-2-amino aniline 
• 104-86-9 4-chlorobenzylamine 
• 88-73-3 2-Chloronitrobenzene 
• 4857-04-9 2-chloromethyl-1H-benzimidazole 
• 2948-92-7 2-(pyrrolidin-1-ylmethyl)-1H-benzo[d]imidazole 
• 54600-29-2 1-((trimethylsilyl)methyl)pyrrolidine 
• 57159-81-6 2-(methylsulfonyl)-1H-benzo[d]imidazole 

Downstream Products

• 1251554-58-1 1-(4-chlorobenzyl)-2-(d2-(pyrrolidin-1-yl)methyl)-1H-benzo[d]imidazole 
• 1163-36-6 clemizole hydrochloride 

Relevant articles and documents

Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y

A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.

Hypervalent iodine-mediated synthesis of benzoxazoles and benzimidazoles via an oxidative rearrangement

A Beckmann-type rearrangement of o-hydroxy and o-aminoaryl N-H ketimines has been developed to prepare benzoxazoles and N-Ts benzimidazoles, respectively. The ketimine derivatives were easily prepared by condensation of ammonia with the corresponding ketones and (diacetoxyiodo)benzene was found to act as an efficient oxidant to trigger the [1,2]-aryl migration towards the formation of the desired heterocycles. Depending on the substitution pattern, the results revealed another mechanistic pathway through which benzisoxazoles or 1H-indazoles could be formed. The Beckmann-type rearrangement strategy was applied to the synthesis of benzimidazole-containing biorelevant targets such as chlormidazole and clemizole.

Selective inhibition of heme oxygenase-2 activity by analogs of 1-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole (clemizole): Exploration of the effects of substituents at the N-1 position

Several analogs based on the lead structure of 1-(4-chlorobenzyl)-2- (pyrrolidin-1-ylmethyl)-1H-benzimidazole (clemizole) were synthesized and evaluated as novel inhibitors of heme oxygenase (HO). Many of the compounds were found to be potent and highly s

BENZIMIDAZOLE MODULATORS OF H1 RECEPTOR AND/OR NS4B PROTEIN ACTIVITY

The present invention relates to new benzimidazole modulators of H1 receptor activity and/or inhibitors of NS4B protein activity, pharmaceutical compositions thereof, and methods of use thereof formula (I).