30486-73-8

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a promising candidate for the development of new drugs with improved efficacy and safety profiles.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE is used as a building block for the design and synthesis of novel bioactive molecules. Its presence in drug candidates can potentially enhance their pharmacokinetic and pharmacodynamic properties, leading to more effective therapeutic agents.
Used in Biochemical Studies:
5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE can be employed as a research tool in biochemical studies to investigate the structure-activity relationships of benzimidazole-based compounds. This knowledge can be applied to optimize the design of new drugs with specific biological targets.
Used in Drug Discovery:
As a part of drug discovery efforts, 5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE can be utilized in high-throughput screening assays to identify potential lead compounds with therapeutic potential. Its unique chemical properties may contribute to the discovery of new drugs for various diseases and conditions.
Used in Chemical Synthesis:
5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE can be used as a reagent or catalyst in various chemical synthesis processes. Its unique structure and properties may enable the development of new synthetic routes and methodologies, contributing to the advancement of chemical science.

InChI:InChI=1/C7H6FN3/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H,(H3,9,10,11)

Upstream product

• 506-68-3 bromocyane 
• 367-31-7 4-fluoro-1,2-phenylenediamine 
• 364-78-3 2-nitro-4-fluoroaniline 

Downstream Products

• 1403758-00-8 (3-((6-fluoro-1H-benzo[d]imidazol-2-yl)amino)phenyl)(morpholino)methanone 

Relevant academic research and scientific papers

MRGX Receptor Antagonists

The invention relates to a method for preventing or treating a disease or disorder that is associated with the MrgX2 receptor. The invention also relates to MrgX2 antagonists and physiologically acceptable salts thereof. The invention also relates to pharmaceutical compositions and dosage forms comprising an MrgX2 antagonist.

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.

ARYL HYDROCARBON RECEPTOR ACTIVATORS

Small molecule AhR ligands are disclosed. The ligands can induce the differentiation of Tr1 cells to suppress pathogenic immune responses without inducing nonspecific immune suppression. Methods of treatment of autoimmune diseases using the AhR ligands are also disclosed.

Lewis-acid Promoted Chemoselective Condensation of 2-Aminobenzimidazoles or 3-Aminoindazoles with 3-Ethoxycyclobutanones to Construct Fused Nitrogen heterocycles

A Lewis-acid promoted chemoselective condensation of 2-aminobenzimidazoles or 3-aminoindazoles with 3-ethoxycyclobutanones is presented. Diverse fused heterocycles benzo[4,5]-imidazo[1,2-a]pyrimidine and pyrimido[1,2-b]-indazole derivatives were obtained in moderate to high yields under mild conditions, the reaction mechanism of which was in sharp contrast to previous [3+3] annulation reaction of 3-ethoxycyclobutanones. (Figure presented.).

Cu-Catalyzed Synthesis of 3-Formyl Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources

A highly efficient synthesis of 3-formyl imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine, under Cu-catalyzed aerobic oxidative conditions and by utilizing ethyl tertiary amines as carbon sources, is disclosed. A novel activation mode of ethyl tertiary amines in which simultaneous selective cleavage of C-C bond and C-N bond of ethyl group with molecular oxygen as terminal oxidant in this one-pot protocol is reported for the first time. This reaction features broad substrate scope, good functional group tolerance, as well as diversified and valuable products.

Design, synthesis and biological evaluation of benzimidazolyl and benzothiazolyl picolinamide derivatives as antimicrobial agents

A series of benzothiazolyl amides and benzimidazolyl amides (6a-f) has been synthesized from the coupling reaction of substituted picolinic acid with benzothiazole and benzimidazoles, respectively. The newly synthesized compounds were evaluated for their efficacy as antimicrobial agents against various Gram-positive and Gram-negative strains of bacteria and fungal strains. Amongst these compounds 6f was found to be the most potent against Bacillus subtilis and Candida albicans. Moreover, other compounds also found to be potential antibacterial agents in comparison to the standard drugs.

Inhibition and Dispersion of Bacterial Biofilms with 2-Aminobenzimidazole Derivatives

Compounds described herein inhibit biofilm formation or disperse pre-formed biofilms of Gram-negative bacteria. Biofilm-inhibitory compounds can be encapsulated or contained in a polymer matrix for controlled release. Coatings, films, multilayer films, hydrogels, microspheres and nanospheres as well as pharmaceutical compositions and disinfecting compositions containing biofilm-inhibitory compounds are also provided. Methods for inhibiting formation of biofilms or dispersing already formed biofilms are provided. Methods for treating infections of gram-negative bacteria which form biofilms, particularly those of Pseudomonas and more particularly P. aeruginosa.

2-aminobenzimidazole derivatives strongly inhibit and disperse Pseudomonas aeruginosa biofilms

Bacterial biofilms are exceptionally difficult to clear using traditional antibiotics and constitute a significant health threat. 2-Aminobenzimidazole derivatives (see scheme) are capable of strongly inhibiting the growth of and dispersing Pseudomonas aeruginosa biofilms. These molecules were found to modulate quorum sensing in reporter strains, and represent some of strongest P. aeruginosa biofilm inhibitors known. Copyright

Catalyst-controlled chemoselective arylation of 2-aminobenzimidazoles

What N would you like? The chemoselective and complementary Pd- and Cu-catalyzed N-arylation of 2-aminobenzimidazoles is described. Selective N-arylation of the amino group was achieved with a Pd-catalyzed method, while selective N-arylation of azole nitrogen was achieved with a Cu-catalyzed procedure (see scheme). Copyright

JAK-2 MODULATORS AND METHODS OF USE

This invention relates to the field of protein tyrosine kinases and inhibitors thereof. In particular, the invention relates to inhibitors of JAK-2, pharmaceutical compositions of the compounds for inhibiting JAK-2, methods of inhibiting JAK-2 in a cell, comprising contacting a cell in which inhibition of JAK-2 is desired with a compound or pharmaceutical composition comprising a compound according to the invention. The also comprises methods of treating a disease or condition that involves JAK-2 comprising administering to a patient a pharmaceutical composition comprising a compound according to the invention