137898-68-1

Basic information

• Product Name: 1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole
• Synonyms: 1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole;1-methyl-2-(piperazin-1-yl)-1H-1,3-benzodiazole;1-methyl-2-(1-piperazinyl)-1H-benzimidazole
• CAS NO: 137898-68-1
• Molecular Formula: C₁₂H₁₆N₄
• Molecular Weight: 216.28224
• Mol File: 137898-68-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 393.4±52.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• PKA: 8.74±0.10(Predicted)
• CAS DataBase Reference: 1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole(137898-68-1)
• EPA Substance Registry System: 1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole(137898-68-1)

Safety Data

• Hazardous Substances Data: 137898-68-1(Hazardous Substances Data)

Usage

Chemical class

Benzoimidazole derivatives
A class of chemical compounds that includes 1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole.

Structure

Benzo[d]imidazole ring
The core structure of the compound, which consists of a fused benzene and imidazole ring system.

Substituents

Methyl group and piperazin-1-yl group
The two functional groups attached to the benzo[d]imidazole ring, which influence the compound's properties and activities.

Methyl group attachment

Position 1
The location of the methyl group on the benzo[d]imidazole ring, contributing to the compound's structure and properties.

Piperazin-1-yl group attachment

Position 2
The location of the piperazin-1-yl group on the benzo[d]imidazole ring, contributing to the compound's structure and properties.

Pharmaceutical applications

Potential uses
The possible roles of 1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole in the development of new drugs due to its unique structure and biological activities.

Biological activities

Antiproliferative, antitumor, and antiparasitic properties
The compound's ability to inhibit cell growth, prevent tumor formation, and combat parasitic infections, which may contribute to its therapeutic potential.

Building block in synthesis

Pharmacologically active molecules
The use of 1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole as a starting material in the creation of other biologically active compounds with potential pharmaceutical applications.

Therapeutic benefits

Treatment of certain diseases
The potential for 1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole to be used in the treatment of specific health conditions due to its unique structure and biological activities.

Research and development

Pharmaceutical industry
The importance of 1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole in ongoing research and development efforts within the pharmaceutical industry as a potential drug candidate.

Upstream product

• 110-85-0 piperazine 
• 1849-02-1 2-chloro-1-methyl-benzimidazole 
• 4857-06-1 2-chloro-1H-benzoimidazole 
• 145909-58-6 ethyl 4-(1-methyl-benzimidazol-2-yl)-piperazin-1-carboxylate 

Downstream Products

• 432499-78-0 1-methyl-2-[4-(p-tolylsulfonyl)piperazin-1-yl]benzimidazole 
• 604741-57-3 2-[4-(benzenesulfonyl)piperazin-1-yl]-1-methyl-1H-1,3-benzimidazole 
• 1235095-99-4 2-[4-(4-tert-butylphenyl)sulfonylpiperazin-1-yl]-1-methyl-benzimidazole 
• 604741-60-8 2-[4-(4-methoxyphenyl)sulfonylpiperazin-1-yl]-1-methyl-benzimidazole 
• 1234862-75-9 2-[4-(3,4-dimethoxyphenyl)sulfonylpiperazin-1-yl]-1-methyl-benzimidazole 
• 1454676-38-0 2-[4-(4-methoxy-3-nitro-phenyl)sulfonylpiperazin-1-yl]-1-methyl-benzimidazole 
• 1454676-39-1 4-[4-(1-methylbenzimidazol-2-yl)piperazin-1-yl]sulfonylbenzoic acid 
• 1454676-40-4 3-[4-(1-methylbenzimidazol-2-yl)piperazin-1-yl]sulfonylbenzoic acid 
• 1454676-41-5 4-[4-(1-methylbenzimidazol-2-yl)piperazin-1-yl]sulfonylbenzenecarbohydroxamic acid 
• 1454676-42-6 3-[4-(1-methylbenzimidazol-2-yl)piperazin-1-yl]sulfonylbenzenecarbohydroxamic acid 
• 348134-17-8 9-{4-[4-(1-methyl-1H-benzimidazol-2-yl)-piperazin-1-yl]-butyl}-9H-fluorene-9-carboxylic Acid-4-fluoro-benzylamide 
• 138490-66-1 N-[4-[[4-(1-methyl-1H-benzimidazol-2-yl)-1-piperazinyl]sulfonyl]phenyl]methanesulfonamide 
• 137898-90-9 N-<4-<2-hydroxy-3-<4-(1-methyl-1H-benzimidazol-2-yl)-1-piperazinyl>propoxy>phenyl>methanesulfonamide 
• 138490-68-3 N-{4-[4-(1-Methyl-1H-benzoimidazol-2-yl)-piperazine-1-carbonyl]-phenyl}-methanesulfonamide 

Relevant articles and documents

2-Benzazolyl-4-Piperazin-1- Ylsulfonylbenzenecarbohydroxamic acids as novel selective histone deacetylase-6 inhibitors with antiproliferative activity

We have screened our compound collection in an established cell based assay that measures the derepression of an epigenetically silenced transgene, the locus derepression assay. The screen led to the identification of 4-[4-(1-methylbenzimidazol-2-yl)piperazin-1- yl]sulfonylbenzenecarbohydroxamic acid (9b) as an active which was found to inhibit HDAC1. In initial structure activity relationships study, the 1-methylbenzimidazole ring was replaced by the isosteric heterocycles benzimidazole, benzoxazole, and benzothiazole and the position of the hydroxamic acid substituent on the phenyl ring was varied. Whereas compounds bearing a para substituted hydroxamic acid (9a-d) were active HDAC inhibitors, the meta substituted analogues (8a-d) were appreciably inactive. Compounds 9a-d selectively inhibited HDAC6 (IC50 = 0.1-1.0μM) over HDAC1 (IC50 = 0.9-6μM) and moreover, also selectively inhibited the growth of lung cancer cells vs. patient matched normal cells. The compounds induce a cell cycle arrest in the S-phase while induction of apoptosis is neglible as compared to controls. Molecular modeling studies uncovered that the MMGBSA energy for interaction of 9a-d with HDAC6 was higher than for HDAC1 providing structural rationale for the HDAC6 selectivity.

TRIAZOLE DERIVATIVES HAVING ANTIFUNGAL ACTIVITY, METHOD FOR THE PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

A triazole derivative of formula 1 or a pharmaceutically acceptable salt, hydrate, solvate or isomer thereof is superior to the conventional antifungal drugs in antifungal activity against a wide spectrum of pathogenic fungi, and has advantageously low toxicity.

New 2-piperazinylbenzimidazole derivatives as 5-HT3 antagonists. Synthesis and pharmacological evaluation

A series of 2-piperazinylbenzimidazole derivatives were prepared and evaluated as 5-HT3 receptor antagonists. Their 5-HT3 receptor affinities were evaluated by radioligand binding assays, and their abilities to inhibit the 5-HT-induced Bezold-Jarisch reflex in anesthetized rats were determined. Compound 7e (lerisetron, pK(i) = 9.2) exhibited higher affinity for the 5- HT3 receptor than did tropisetron and granisetron, while compound 7q (pK(i) = 7.5) had very low affinity for this receptor, showing that substitution on the N1 atom of the benzimidazole ring is essential for affinity and activity. The effect of substitution on the aromatic ring of benzimidazole by several substituents in different positions is also discussed. A strong correlation between the 5-HT3 antagonistic activity of the studied compounds and the position of substitution on the aromatic ring was established. Thus, while the 4-methoxy derivative 7m showed weak affinity for the 5-HT3 receptor (pK(i) = 6.7), the 7-methoxy derivative 7n exhibited the highest affinity (pK(i) = 9.4). Compounds 7e and 7n are now under further investigation as drugs for the treatment of nausea and emesis evoked by cancer chemotherapy and radiation.