57260-68-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(1-PIPERAZINO)-BENZIMIDAZOLE is used as a pharmaceutical agent for its antihistaminic effects, targeting the relief of allergy symptoms by blocking the action of histamine.
2-(1-PIPERAZINO)-BENZIMIDAZOLE is used as an antipsychotic agent, potentially aiding in the treatment of psychiatric disorders by influencing specific neurotransmitter systems in the brain.
2-(1-PIPERAZINO)-BENZIMIDAZOLE is used as an anti-inflammatory agent, potentially reducing inflammation and associated symptoms by modulating the body's immune response.
2-(1-PIPERAZINO)-BENZIMIDAZOLE is used as an anti-cancer agent, with potential to inhibit cancer cell growth and proliferation, offering a new avenue for cancer treatment and research.

InChI:InChI=1/C11H14N4/c1-2-4-10-9(3-1)13-11(14-10)15-7-5-12-6-8-15/h1-4,12H,5-8H2,(H,13,14)

Upstream product

• 110-85-0 piperazine 
• 4857-06-1 2-chloro-1H-benzoimidazole 
• 295341-56-9 tert-butyl 4-(1H-benzimidazol-2-yl)piperazine-1-carboxylate 
• 749878-99-7 ethyl 4-(1H-benzimidazol-2-yl)-piperazin-1-carboxylate 
• 142-64-3 piperazine dihydrochloride 
• 7542-23-6 piperazine hydrochloride 
• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 295790-30-6 N-(2-(4-(1H-benzimidazol-2-yl)piperazin-1-yl)ethyl)-2,4,5-trichloro-N-methyl-benzenesulfonamide 
• 1061517-13-2 C₂₉H₂₈N₆O₂ 
• 1209218-74-5 2-[4-(p-tolylsulfonyl)piperazin-1-yl]-1H-benzimidazole 
• 1454676-43-7 [4-(1H-benzimidazol-2-yl)piperazin-1-yl]-(p-tolyl)methanone 
• 1159096-83-9 C₂₄H₂₂N₄O 

Relevant academic research and scientific papers

Design, synthesis, characterization and evaluation of 1,3,5-triazine-benzimidazole hybrids as multifunctional acetylcholinesterases inhibitors

A series of hybrids of benzimidazole and 1,3,5-triazine were designed and synthesized and evaluated as multi-target agents for the treatment of Alzheimer's disease. 24 compounds were designed, synthesized and identified by NMR, IR, HRMS and single-crystal X-ray diffraction studies. The compound 6c had the crystal system of orthorhombic and the space group of P212121. The cholinesterase inhibitory activity of synthesized compounds was measured using colorimetric Ellman's method. Most 1,3,5-triazine-benzimidazole hybrids showed potent acetylcholinesterase-inhibition activities and weak butyrylcholinesterase inhibitory activities. Compound 9f possessed the best acetylcholinesterase inhibitory activity with the IC50 of 0.044 μM, which is better than donepezil (0.052 μM). Molecular docking and molecular dynamics simulations demonstrated that there is a stable interaction between compound 9f and acetylcholinesterase. Simultaneously, experiments have also proved that compound 9f has good metal chelating properties. ADMET in silico prediction results suggest the compound can pass through the blood-brain barrier well and have good drug similarity. So, compound 9f could be a multi-target agent for the treatment of Alzheimer's disease.

Microwave use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds method

The invention discloses a microwave the use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds, in the aqueous phase under microwave conditions adding benzoic amidine compound under alkaline condition [...] into benzimidazole reaction, invention an environment-friendly, the operation is simple, cheap and safe, efficient process for preparing benzimidazole method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection; .

Small-compound enhancers for functional O-mannosylation of alpha-dystroglycan, and uses thereof

The present invention provides compounds that can enhance functional O-mannosylation of proteins including alpha-dystroglycan. Also provided are methods of preparation of the compounds defined by the formula I. Also provided are the methods of using the compounds or the pharmaceutical acceptable salts or prodrugs thereof in treating and preventing subjects suffering from the diseases including muscular dystrophies and cancers.

Benzimidazole derivative and preparation method and application thereof

The invention discloses a benzimidazole derivative and a preparation method and the application thereof. The prepared benzimidazole derivative is capable of effectively reducing the relapse arte afterabstaining from morphine addiction, has a remarkable ef

From Cells to Mice to Target: Characterization of NEU-1053 (SB-443342) and Its Analogues for Treatment of Human African Trypanosomiasis

Human African trypanosomiasis is a neglected tropical disease that is lethal if left untreated. Existing therapeutics have limited efficacy and severe associated toxicities. 2-(2-(((3-((1H-Benzo[d]imidazol-2-yl)amino)propyl)amino)methyl)-4,6-dichloro-1H-indol-1-yl)ethan-1-ol (NEU-1053) has recently been identified from a high-throughput screen of >42,000 compounds as a highly potent and fast-acting trypanocidal agent capable of curing a bloodstream infection of Trypanosoma brucei in mice. We have designed a library of analogues to probe the structure-activity relationship and improve the predicted central nervous system (CNS) exposure of NEU-1053. We report the activity of these inhibitors of T. brucei, the efficacy of NEU-1053 in a murine CNS model of infection, and identification of the target of NEU-1053 via X-ray crystallography.

Small molecules enhance functional O-mannosylation of Alpha-dystroglycan

Alpha-dystroglycan (α-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biological processes. Hypoglycosylation of α-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of α-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of α-DG in response to certain chemical stimuli, we developed a cell-based high-throughput screening (HTS) platform for searching chemical enhancers of FOG of α-DG from a large chemical library with 364,168 compounds. Sequential validation of the hits from a primary screening campaign and chemical works led to identification of a cluster of compounds that positively modulate FOG of α-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of α-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy.

A Developability-Focused Optimization Approach Allows Identification of in Vivo Fast-Acting Antimalarials: N -[3-[(Benzimidazol-2-yl)amino]propyl]amides

Malaria continues to be a major global health problem, being particularly devastating in the African population under the age of five. Artemisinin-based combination therapies (ACTs) are the first-line treatment recommended by the WHO to treat Plasmodium falciparum malaria, but clinical resistance against them has already been reported. As a consequence, novel chemotypes are urgently needed. Herein we report a novel, in vivo active, fast-acting antimalarial chemotype based on a benzimidazole core. This discovery is the result of a medicinal chemistry plan focused on improving the developability profile of an antichlamydial chemical class previously reported by our group. (Graph Presented).

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.

Arylation of amines and monoarylation of symmetrical diamines in the presence of brine solution with diheteroaryl halides

A simple, scalable, ligand-free, and metal-free protocol for arylation of amines and monoarylation of symmetrical diamines with diheteroaryl halides in the presence of brine solution has been developed. The protocol has broad structural applicability for chemoselective monoarylation of a wide variety of symmetrical, cyclic, and acyclic aliphatic diamines. The protocol is also applicable for selective arylation of aliphatic amine in the presence of aromatic amine.

Synthesis and biological analysis of benzazol-2-yl piperazine sulfonamides as 11β-hydroxysteroid dehydrogenase 1 inhibitors

In the last decade the inhibition of the enzyme 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1) emerged as a promising new strategy to treat diabetes and several metabolic syndrome phenotypes. Using a molecular modeling approach and classical bioisosteric studies, we discovered a new class of 11β-HSD1 inhibitors bearing an arylsulfonylpiperazine scaffold. Optimization of the initial lead resulted in compound 11 that selectively inhibits 11β-HSD1 (IC50 = 0.7 μM).