1622-57-7

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-1-METHYLBENZIMIDAZOLE is used as a chemical intermediate for the preparation of various compounds, such as 2or 3-carboxy-4H-pyrimido[2,1-b]-benzazol-4-ones and novel functionalized spiropyran derivatives of the 2H-1,3-benzoxazinone series. These compounds have potential applications in the development of new drugs and therapeutic agents.
Used in Chemical Research:
2-AMINO-1-METHYLBENZIMIDAZOLE serves as a valuable compound for researchers in the field of organic chemistry, particularly in the study of carbonyl-scavenging properties and Menshutkin reactions. Its ability to form adducts with various isothiocyanates also makes it a useful tool for exploring the chemical properties and reactivity of these compounds.

InChI:InChI=1/C8H9N3/c1-11-7-5-3-2-4-6(7)10-8(11)9/h2-5H,1H3,(H2,9,10)

Upstream product

• 934-32-7 1H-benzimidazol-2-amine 
• 74-88-4 methyl iodide 
• 122128-74-9 3-methyl-1-(p-methoxybenzylidene)aminobenzimidazoline-2-imine 
• 1516-73-0 2-azido-1-methyl-1H-benzo[d]imidazole 
• 49572-60-3 2-bromo-1-methyl-1H-benzo[d]imidazole 
• 1632-83-3 1-Methylbenzimidazole 
• 78620-29-8 1-methylbenzimidazole-2-carboxylic acid hydrazide 
• 5533-38-0 1-methyl-1H-benzo[d]imidazole-2-sulfonic acid 
• 35342-97-3 ethyl 1-methyl-1H-benzo[d]imidazole-2-carboxylate 
• 506-68-3 bromocyane 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 13734-28-6 Boc-Lys-OH 
• 98711-52-5 1-methyl-3-(1-methyl-1,2,4-triazol-4-ylio)benzimidazolium bis-(methyl sulphate) 
• 122128-75-0 3-methyl-1-(p-nitrobenzylidene)aminobenzimidazoline-2-imine 

Downstream Products

• 123767-95-3 1-Methyl-2-(o-chlorobenzamide)benzimidazole 
• 144836-22-6 (1-Methyl-1H-benzoimidazol-2-yl)-[1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-amine 
• 24486-75-7 1-(1-methyl-1H-benzoimidazol-2-yl)-3-phenyl-urea 
• 144836-18-0 2-Methoxy-4-{[(E)-1-methyl-1H-benzoimidazol-2-ylimino]-methyl}-phenol 
• 122128-76-1 N-(1-methyl-2-benzimidazolyl)benzamidine 
• 87483-50-9 3,5-Dimethyl-2-(1-methyl-1H-benzoimidazol-2-ylazo)-phenylamine 
• 87483-46-3 3,5-Dimethyl-4-(1-methyl-1H-benzoimidazol-2-ylazo)-phenylamine 
• 87483-53-2 1,3-bis(1'-methyl-2'-benzimidazolyl)-triazene 
• 87494-42-6 2-(2',6'-xylylazo)-1-methylbenzimidazoles 
• 39860-02-1 2-(2',4'-xylylazo)-1-methylbenzimidazole 
• 87494-43-7 (2,5-Dimethyl-phenyl)-(1-methyl-1H-benzoimidazol-2-yl)-diazene 
• 87494-44-8 (1-Methyl-1H-benzoimidazol-2-yl)-(2,3,5,6-tetramethyl-phenyl)-diazene 
• 134937-74-9 N-(2,6-Dichloro-phenyl)-2-(2-imino-3-methyl-2,3-dihydro-benzoimidazol-1-yl)-acetamide 
• 117651-71-5 N-Adamantan-1-yl-2-(2-imino-3-methyl-2,3-dihydro-benzoimidazol-1-yl)-acetamide; hydrochloride 

Relevant academic research and scientific papers

2-aminobenzimidazoles for leishmaniasis: From initial hit discovery to in vivo profiling

Leishmaniasis is a major infectious disease with hundreds of thousands of new cases and over 20,000 deaths each year. The current drugs to treat this life-threatening infection have several drawbacks such as toxicity and long treatment regimens. A library of 1.8 million compounds, from which the hits reported here are publicly available, was screened against Leishmania infantum as part of an optimization program; a compound was found with a 2-aminobenzimidazole functionality presenting moderate potency, low metabolic stability and high lipophilicity. Several rounds of synthesis were performed to incorporate chemical groups capable of reducing lipophilicity and clearance, leading to the identification of compounds that are active against different parasite strains and have improved in vitro proper-ties. As a result of this optimization program, a group of compounds was further tested in anticipation of in vivo evaluation. In vivo tests were carried out with compounds 29 (L. infantum IC50: 4.1 μM) and 39 (L. infantum IC50: 0.5 μM) in an acute L. infantum VL mouse model, which showed problems of poor exposure and lack of efficacy, despite the good in vitro potency.

HMOX1 inducers

The present invention is related to compounds of structure (I) as heme oxygenase 1 (HMOX 1) inducers. The present invention is also related a method of controlling the activity or the amount, or both the activity and the amount, of heme-oxygenase 1 in a mammalian subject. The definitions of the variables are provided herein.

Hit-to-lead optimization of novel benzimidazole phenylacetamides as broad spectrum trypanosomacides

Trypanosoma cruzi and Trypanosoma brucei are the parasitic causative agents of Chagas disease and human African trypanosomiasis (HAT), respectively. The drugs currently used to treat these diseases are not efficacious against all stages and/or parasite sub-species, often displaying side effects. Herein, we report the SAR exploration of a novel hit, 2-(4-chlorophenyl)-N-(1-propyl-1H-benzimidazol-2-yl)acetamide previously identified from high throughput screens against T. cruzi, Trypanosoma brucei brucei and Leishmania donovani. An informative set of analogues was synthesized incorporating key modifications of the scaffold resulting in improved potency whilst the majority of compounds retained low cytotoxicity against H9c2 and HEK293 cell lines. The SAR observed against T. cruzi broadly matches that observed against T.b. brucei, suggesting the possibility for a broad-spectrum candidate. This class of compounds therefore warrants further investigation towards development as a treatment for Chagas disease and HAT. This journal is

Benzimidazole compound and application thereof

The invention relates to a benzimidazole compound and an application thereof. The structure of the benzimidazole compound is shown as a formula I, and the compound is used as a focal adhesion kinase inhibitor and shows relatively good focal adhesion kinase (FAK) inhibition activity. Meanwhile, the benzimidazole compound has stronger medicine effect and better pharmacokinetic property and/or toxicological characteristics, such as good brain/plasma ratio, good bioavailability, good metabolic stability, and reduced inhibition to respiratory action of mitochondria. The benzimidazole compound has agood clinical application prospect.

Metal-free C(sp2)-H functionalization of azoles: K2CO3/I2-mediated oxidation, imination, and amination

The direct C2-H oxidation and imination of a wide variety of azoles was achieved by using a commercially available simple K2CO3/I2 reagent combination. The iodinated azole adduct, produced via the in situ generation of N-heterocyclic carbene, is the key intermediate for C2-H oxidation, imination, and amination of azoles. Significantly, these reactions proceed under mild conditions with high to excellent yields, are scalable to large quantity and exhibit a broad substrate scope. Interestingly, this direct C2-H imination method allowed us to access various pharmacologically active N6-alkyl or N6-aryl substituted benzimidazoquinazolinone scaffolds through intramolecular C-H imination in a sequential one-pot reaction.

Synthesis and pharmacological activity of 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles

An efficient method for the synthesis of novel 9H-imidazo[1,2-a]benzimidazole derivatives containing a biphenyl substituent at position 2 was developed. These compounds, belonging to the privileged substructures, have been tested for a wide range of pharmacological activities in the in vitro test panel. It was shown that the synthesized derivatives demonstrated high antioxidant activity, some of them inhibit type 1B protein tyrosine phosphatase, activate AMP-activated protein kinase, possess antiplatelet properties, and a rare and very interesting kind of activity, the ability to break cross-links of glycated proteins. The most active compounds can be suggested for further optimization.

PHOTOREDOX-CATALYZED DIRECT C-H FUNCTIONALIZATION OF ARENES

The invention generally relates to methods of making substituted arenes via direct C-H amination. More specifically, methods of making para- and ortho-substituted arenes via direct C-H amination are disclosed. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Water compatible photoarylation of amino acids and peptides

A novel photoarylation of amino acids and peptides is described, which tolerates the presence of water. Irradiation of Boc-protected amino acids in the presence of N-protected 2-azidobenzimidazoles leads to selective arylation of carboxy termini or side chains. The new reaction also works for peptides. Irradiation of the nonapeptide H-SPSYVYHQF-OH also resulted in selective arylation of the tyrosine side chains, as indicated by ESI-MS/MS fragmentation. Chemo- and regioselectivity could add the title reaction to the repertoire of photoaffinity labeling methods.

Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action

In this report we describe 2-iminobenzimidazole (IBI) analogs, identified during the course of a phenotypic high-throughput screening campaign, as novel hepatitis C virus (HCV) inhibitors. A series of IBI derivatives was synthesized and evaluated for their inhibitory activity against infectious HCV. Among the IBIs derivatives studied in this work, we identified promising compounds with high antiviral efficacy, high selectivity index and good microsomal stability. Noteworthy, the IBI series exhibited inhibitory activity on early and late steps of the viral cycle, but not in the HCV replicon system demonstrating a mechanism of action distinct from clinical-stage and approved anti-HCV drugs. Overall, our results suggest that IBIs are predestinated for further exploration as lead compounds for novel HCV interventions.

Benzazoles: II.* synthesis and arenesulfonylation of 1-methyl-1H-benzimidazol-2-amine

The reaction of 1-methyl-1H-benzimidazol-2-amine with arenesulfonyl chlorides in the presence of triethylamine afforded 1-arenesulfonyl-3-methyl-2, 3-dihydro-1H-benzimidazol-2-imines instead of expected N-(1-methyl-1H- benzimidazol 2-yl)arenesulfonamides.