51592-02-0

Usage

Uses

Used in Chemical Synthesis:
1-N-butylbenzene-1,2-diamine is used as a chemical intermediate for the synthesis of various compounds, including dyes, pharmaceuticals, and other specialty chemicals. Its versatile structure allows for further functionalization and modification to create a wide range of products.
Used in Fluorescent Probes:
1-N-butylbenzene-1,2-diamine is used as a key component in the synthesis of a fluorescent probe for imaging Cu(II) in living cells. The probe allows for the detection and monitoring of copper ions, which are essential for various biological processes but can also be toxic in excess. This application is particularly relevant in the fields of cell biology, neuroscience, and toxicology.
Used in Analytical Chemistry:
1-N-butylbenzene-1,2-diamine can be employed as a reagent in analytical chemistry for the detection and quantification of metal ions, particularly copper. Its ability to form stable complexes with metal ions makes it a valuable tool for developing sensitive and selective analytical methods.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-N-butylbenzene-1,2-diamine may be used as a building block for the development of new drugs, particularly those targeting metal ion-related diseases or conditions. Its unique chemical properties can be exploited to design molecules with specific biological activities.
Used in Material Science:
1-N-butylbenzene-1,2-diamine can also be utilized in the development of new materials, such as polymers and coatings, that exhibit specific properties, such as conductivity, stability, or reactivity. Its chemical structure can be tailored to meet the requirements of various applications in material science.

Upstream product

• 42896-66-2 o-Nitro-N-n-butylaminobenzene 
• 7788-71-8 n-butyl-2,1,3-benzothiadiazolium 2,4-dinitrobenzenesulphonate 
• 109-69-3 n-Butyl chloride 
• 15223-25-3 N,N-dibenzylidenebenzene-1,2-diamine 
• 88-73-3 2-Chloronitrobenzene 
• 109-65-9 1-bromo-butane 
• 95-54-5 1,2-diamino-benzene 
• 1493-27-2 ortho-nitrofluorobenzene 

Downstream Products

• 88016-67-5 1-Butyl-2-(2'-hydroxy-5'-nitrophenyl)-benzimidazol 
• 88016-58-4 1-Butyl-2-(2'-hydroxyphenyl)-benzimidazol 
• 600725-64-2 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-carboxylic acid [(R)-2-(4-amino-3,5-dibromo-phenyl)-1-(2-butylamino-phenylcarbamoyl)-ethyl]-amide 
• 815581-69-2 N-(n-butyl)-2-(2-bromophenyl)-benzimidazole 
• 24107-62-8 1-butyl-2-phenyl-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Cell-Based Drug Discovery: Identification and Optimization of Small Molecules that Reduce c-MYC Protein Levels in Cells

Elevated expression of the c-MYC oncogene is one of the most common abnormalities in human cancers. Unfortunately, efforts to identify pharmacological inhibitors that directly target MYC have not yet yielded a drug-like molecule due to the lack of any known small molecule binding pocket in the protein, which could be exploited to disrupt MYC function. We have recently described a strategy to target MYC indirectly, where a screening effort designed to identify compounds that can rapidly decrease endogenous c-MYC protein levels in a MYC-amplified cell line led to the discovery of a compound series that phenocopies c-MYC knockdown by siRNA. Herein, we describe our medicinal chemistry program that led to the discovery of potent, orally bioavailable c-MYC-reducing compounds. The development of a minimum pharmacophore model based on empirical structure activity relationship as well as the property-based approach used to modulate pharmacokinetics properties will be highlighted.

1,2-Disubstituted Benzimidazoles by the Iron Catalyzed Cross-Dehydrogenative Coupling of Isomeric o-Phenylenediamine Substrates

Benzimidazoles are common in nature, medicines, and materials. Numerous strategies for preparing 2-arylbenzimidazoles exist. In this work, 1,2-disubstituted benzimidazoles were prepared from various mono- and disubstituted ortho-phenylenediamines (OPD) by iron-catalyzed oxidative coupling. Specifically, O2 and FeCl3·6H2O catalyzed the cross-dehydrogenative coupling and aromatization of diarylmethyl and dialkyl benzimidazole precursors. N,N′-Disubstituted-OPD substrates were significantly more reactive than their N,N-disubstituted isomers, which appears to be relative to their propensity for complexation and charge transfer with Fe3+. The reaction also converted N-monosubstituted OPD substrates to 2-substituted benzimidazoles; however, electron-poor substrates produce 1,2-disubstituted benzimidazoles by intermolecular imino-transfer. Kinetic, reagent, and spectroscopic (UV-vis and EPR) studies suggest a mechanism involving metal-substrate complexation, charge transfer, and aerobic turnover, involving high-valent Fe(IV) intermediates. Overall, comparative strategies for the relatively sustainable and efficient synthesis of 1,2-disubstituted benzimidazoles are demonstrated.

Novel purine benzimidazoles as antimicrobial agents by regulating ROS generation and targeting clinically resistant Staphylococcus aureus DNA groove

A novel series of purine benzimidazole hybrids were designed and synthesized for the first time with the aim to circumvent the increasing antibiotic resistance. Hexyl appended hybrid 3c gave potent activities against most of the tested bacteria and fungi especially against multidrug-resistant strains Staphylococcus aureus (MIC = 4 μg/mL). Structure-activity relationships revealed that the benzimidazole fragment at the 9-position of purine played an important role in exerting potentially antibacterial activity. Both cell toxicity and ROS generation assays indicated that the purine derivative 3c showed low cytotoxicity and could be used as a safe agent. Molecular modeling suggested that hybrid 3c could bind with the residues of Topo IA through hydrogen bonds and electrostatic interactions. Quantum chemical studies were also performed on the target compound 3c to understand the structural features essential for activity. The active molecule 3c could effectively interact with S. aureus DNA to form 3c–DNA complex through groove binding mode, which might block DNA replication to display their powerful antimicrobial activity.

Discovery of Benzimidazole–Quinolone Hybrids as New Cleaving Agents toward Drug-Resistant Pseudomonas aeruginosa DNA

A series of benzimidazole–quinolone hybrids as new potential antimicrobial agents were designed and synthesized. Bioactive assays indicated that some of the prepared compounds exhibited potent antibacterial and antifungal activities. Notably, 2-fluorobenzyl derivative 5 b (ethyl 7-chloro-6-fluoro-1-[[1-[(2-fluorophenyl)methyl]benzimidazol-2-yl]methyl]-4-oxo-quinoline-3-carboxylate) showed remarkable antimicrobial activity against resistant Pseudomonas aeruginosa and Candida tropicalis isolated from infected patients. Active molecule 5 b could not only rapidly kill the tested strains, but also exhibit low toxicity toward Hep-2 cells. It was more difficult to trigger the development of bacterial resistance of P. aeruginosa against 5 b than that against norfloxacin. Molecular docking demonstrated that 5 b could effectively bind with topoisomerase IV–DNA complexes, and quantum chemical studies theoretically elucidated the good antimicrobial activity of compound 5 b. Preliminary experimental reaction mechanism exploration suggested that derivative 5 b could not intercalate into DNA isolated from drug-resistant P. aeruginosa, but was able to cleave DNA effectively, which might further block DNA replication to exert powerful bioactivities. In addition, compound 5 b is a promising antibacterial agent with membrane disruption abilities.

Cs2CO3-Promoted Direct N-Alkylation: Highly Chemoselective Synthesis of N-Alkylated Benzylamines and Anilines

Herein is described an efficient and chemoselective method for the synthesis of diversely substituted secondary amines in yields up to 98 %. Direct mono-N-alkylation of primary benzylamines and anilines with a wide range of alkyl halides is promoted by a cesium base in the absence of any additive or catalyst. The basicity and solubility of cesium carbonate in anhydrous N,N-dimethylformamide not only enables mono-N-alkylation of primary amines but also suppresses undesired dialkylation of the desired amines.

Imidoyl dichlorides as new reagents for the rapid formation of 2-aminobenzimidazoles and related azoles

The development of a reagent for the efficient synthesis of five- and six-membered azoles at room temperature is proposed. A variety of substituted 2-aminobenzimidazoles are synthesized in good to excellent yields. The ability to incorporate various protecting groups makes the imidoyl dichloride reagent amenable to a large number of syntheses. The reagent is applied to the total synthesis of the 2-aminobenzimidazole containing carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), from 2-chloro-3-nitropyridine in >60% yield in 6 steps.

Discovery of isoalloxazine derivatives as a new class of potential anti-Alzheimer agents and their synthesis

This article describes discovery of a novel and new class of cholinesterase inhibitors as potential therapeutics for Alzheimer's disease. A series of novel isoalloxazine derivatives were synthesized and biologically evaluated for their potential inhibitory outcome for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). These compounds exhibited high activity against both the enzymes AChE as well as BuChE. Of the synthesized compounds, the most potent isoalloxazine derivatives (7m and 7q) showed IC50 values of 4.72 μM and 5.22 μM respectively against AChE; and, 6.98 μM and 5.29 μM respectively against BuChE. These two compounds were further evaluated for their anti-aggregatory activity for β-amyloid (Aβ) in presence and absence of AChE by performing Thioflavin-T (ThT) assay and Congo red (CR) binding assay. In order to evaluate cytotoxic profile of these two potential compounds, cell viability assay of SH-SY5Y human neuroblastoma cells was performed. Further, to understand the binding behavior of these two compounds with AChE and BuChE enzymes, docking studies have been reported.

Metal-free TEMPO-promoted C(sp3)-H amination to afford multisubstituted benzimidazoles

An efficient TEMPO-air/cat. TEMPO-O2 oxidative protocol was developed to synthesize multisubstituted or fused tetracyclic benzimidazoles via a metal-free oxidative C-N coupling between the sp3 C-H and free N-H of readily available N1-benzyl/alkyl-1,2-phenylenediamines.

Intensely blue-fluorescent 2,5-bis(benzoimidazol-2-yl)pyrazine dyes with improved solubility: Their synthesis, fluorescent properties, and application as microenvironment polarity probes

In order to improve the solubility of intensively fluorescent 2,5-bis(benzimidazol-2-yl)pyrazine (BBIP), we synthesized new BBIP derivatives (2, 3a,b, and 5a,b) possessing two alkyl chains at the N-1 and N-1′ positions of the two benzimidazole moieties. C

QUINOXALINONE DERIVATIVES AS INSULIN SECRETION STIMULATORS, METHODS FOR OBTAINING THEM AND USE THEREOF FOR THE TREATMENT OF DIABETES

The present invention relates to quinoxalinone derivatives of formula (I), wherein R1, R2, R3, R4, R5 and R6 are as defined in claim 1, as insulin secretion stimulators. The invention also relates to the preparation and use of these quinoxalinone derivatives for the prophylaxis and/or treatment of diabetes and pathologies associated. Other preferred compounds are compounds of general formula (I), wherein R1, R2, R3, R4, R5 and R6 can be optionally substituted by one or more groups selected from Z.