49671-76-3

Usage

Uses

Used in Pharmaceutical Applications:
ZLN005 is used as a therapeutic agent for improving glucose tolerance, pyruvate tolerance, and insulin sensitivity in diabetic individuals, particularly in db/db mice. The application reason is that it increases PGC-1α and downstream gene transcription in skeletal muscles, leading to enhanced fat oxidation and overall metabolic health.
Used in Metabolic Research:
ZLN005 is used as a research tool for studying the role of PGC-1α in energy metabolism, hepatic gluconeogenesis, and cholesterol homeostasis. The application reason is its ability to stimulate the expression of PGC-1α and downstream genes in skeletal muscle cells, providing valuable insights into the molecular mechanisms underlying these processes.
Used in Drug Development:
ZLN005 is used as a lead compound in the development of new drugs targeting metabolic disorders and diabetes. The application reason is its potential to improve glucose utilization and fatty acid oxidation, offering a promising therapeutic approach for managing these conditions.

Upstream product

• 939-97-9 4-tert-Butylbenzaldehyde 
• 95-54-5 1,2-diamino-benzene 
• 4857-06-1 2-chloro-1H-benzoimidazole 
• 123324-71-0 p-tert-butylphenylboronic acid 
• 615-43-0 2-iodophenylamine 
• 18880-00-7 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene 
• 943-27-1 4'-t-butylacetophenone 
• 39895-55-1 4-(1,1-dimethylethyl)-benzenemethanamine 
• 877-65-6 p-tert-butylbenzyl alcohol 
• 88-74-4 2-nitro-aniline 
• 1042161-47-6 C₁₇H₁₈N₄ 

Relevant academic research and scientific papers

Nickel catalyzed sustainable synthesis of benzazoles and purines: Via acceptorless dehydrogenative coupling and borrowing hydrogen approach

Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols. Using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst, [Ni(MeTAA)] (1a), featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)), a wide variety of polysubstituted benzimidazole, purine, benzothiazole, and benzoxazole derivatives were prepared via dehydrogenative coupling of alcohols with 1,2-diaminobenzene, 4,5-diaminopyrimidine, 2-aminothiphenol, and 2-aminophenol, respectively. A wide array of benzimidazoles were also prepared via a borrowing hydrogen approach involving alcohols as hydrogen donors and 2-nitroanilines as hydrogen acceptors. A few control experiments were performed to understand the reaction mechanism.

A heterogeneous catalytic strategy for facile production of benzimidazoles and quinoxalines from primary amines using the Al-MCM-41 catalyst

This study reports a straightforward heterogeneous catalytic (Al-MCM-41) approach to synthesize nitrogen heterocycle moieties from primary amines under solvent-free conditions. The Al-MCM-41 catalyst was prepared using a hydrothermal method and characterized by various analytical techniques. The probability and limitations of the catalytic methodology were presented with various substrates. The catalytic method grants an attractive route to a wide variety of benzimidazole and quinoxaline moieties with good to excellent yields. The gram scale reaction and reusability (up to five cycles) of the Al-MCM-41 catalyst would greatly benefit industrial applications. This journal is

Visible light promoted tandem dehydrogenation-deaminative cyclocondensation under aerobic conditions for the synthesis of 2-aryl benzimidazoles/quinoxalines fromortho-phenylenediamines and arylmethyl/ethyl amines

Visible light promoted domino synthesis of 2-aryl benzimidazoles is reported through the reaction ofortho-phenylenediamines and arylmethyl amines under aerobic conditions. The methodology has wide substrate scope and tolerates a wide range of functional groups affording the products in high yields. The use of arylethyl amines instead of arylmethyl amines gives 2-aryl quinoxalines.

s-Tetrazine-functionalized hyper-crosslinked polymers for efficient photocatalytic synthesis of benzimidazoles

Developing green-safe, efficient and recyclable catalysts is crucial for the chemical industry. So far, organic photocatalysis has been proved to be an environmentally friendly and energy-efficient synthetic technology compared with traditional metal catalysis. As a versatile catalytic platform, hyper-crosslinked polymers (HCPs) with large surface area and high stability are easily prepared. In this report, we successfully constructed two porous HCP photocatalysts (TZ-HCPs) featurings-tetrazine units and surface areas larger than 700 m2g?1through Friedel-Crafts alkylation reactions. The rational energy-band structures and coexisting micro- and mesopores endow TZ-HCPs with excellent activities to realize the green synthesis of benzimidazoles (28 examples, up to 99% yield, 0.5-4.0 h) in ethanol. Furthermore, at least 21 iterative catalytic runs mediated by TZ-HCP1D were performed efficiently, with 96-99% yield. This study of TZ-HCPs sheds light on the wide-ranging prospects of application of HCPs as metal-free and green photocatalysts for the preparation of fine chemicals.

Inhibition of enterovirus a71 by a novel 2-phenyl-benzimidazole derivative

Enterovirus A71 (EV-A71) infection has emerged as a significant public health concern at the global level. Epidemic events of EV-A71 have been reported worldwide, and this succession of outbreaks has heightened concern that EV-A71 may become a public health threat. In recent years, widespread A71 enterovirus also occurred in European countries. EV-A71 infection causes hand-foot-mouth disease (HFMD), herpangina, and fever. However, it can sometimes induce a variety of neurological complications, including encephalitis, aseptic meningitis, pulmonary edema, and acute flaccid paralysis. We identified new benzimidazole derivatives and described theirin vitrocytotoxicity and broad-spectrum anti-enterovirus activity. Among them, derivative 2b resulted in interesting activity against EV-A71, and therefore it was selected for further investigations. Compound 2b proved to be able to protect cell monolayers from EV-A71-induced cytopathogenicity, with an EC50 of 3 μM. Moreover, Vero-76 cells resulted in being significantly protected from necrosis and apoptosis when treated with 2b at 20 and 80 μM. Compound 2b reduced viral adsorption to Vero-76 cells, and when evaluated in a time-of-addition assay, the derivative had the highest effect when added during the infection period. Moreover, derivative 2b reduced viral penetration into host cells. Besides, 2b did not affect intestinal monolayers permeability, showing no toxic effects. A detailed insight into the efficacy of compound 2b against EV-A71 showed a dose-dependent reduction in the viral titer, also at low concentrations. Mechanism of action investigations suggested that our derivative can inhibit viral endocytosis by reducing viral attachment to and penetration into host cells. Pharmacokinetic and toxicity predictions validated compound 2b as a good candidate for furtherin vivoassays.

Visible-Light-Driven Sulfonylation/Cyclization to Access Sulfonylated Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-ones

Visible-light-driven sulfonylation/cyclization of N-methacryloyl-2-phenylbenzoimidazoles has been successfully developed. Using commercially available sulfonyl chloride as sulfonylation reagent, a wide range of sulfonylated benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-ones with potential antitumor activity were provided in acceptable to excellent yields. This method has the advantages of mild reaction conditions and outstanding functional group tolerance, and provides a new strategy for the development of potential antitumor lead compounds.

Visible-Light-Induced Deaminative Alkylation/Cyclization of Alkyl Amines with N-Methacryloyl-2-phenylbenzoimidazoles in Continuous-Flow Organo-Photocatalysis

Herein, we present a metal-free visible-light-induced eosin-y-catalyzed deaminative strategy for the sequential alkylation/cyclization of N-methacryloyl-2-phenylbenzoimidazoles with alkyl amine-derived Katritzky salts, which provides an efficient avenue for the construction of various benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives in moderate to excellent yields under mild reaction conditions. The key enabling feature of this novel reaction includes utilization of redox-active pyridinium salts from abundant and inexpensive primary amine feedstocks that were converted into alkyl radicals via C-N bond scission and subsequent alkylation/cyclization with N-methacryloyl-2-phenylbenzoimidazoles by the formation of two new C-C bonds. In addition, we implemented this protocol for a variety of amino acids, affording the products in moderate yields. Moreover, the novel, environmentally benign batch protocol was further carried out in a continuous-flow regime by utilizing a perfluoroalkoxy alkane tubing microreactor under optimized reaction conditions with a blue light-emitting diode light source, enabling excellent yields and a shorter reaction time (19 min) versus the long reaction time (16 h) of the batch reaction. The reaction displays excellent functional group tolerance, easy operation, scalability, mild reaction conditions, and broad synthetic utility.

Nanoporous Cu doped ZnS nanoparticles an efficient photo catalyst for the chemoselective synthesis of 2-substituted azoles via C-N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence in visible light

ZnS and Cu:ZnS nanoparticles were prepared by aqueous chemical method and characterized by several analytical tools. Nanoparticles have an average size of about ～ 18 nm and possess highly open mesopores, moderate surface area, and uniform morphology. UV–vis spectra designate that doping of Cu shifted the optical response of the ZnS nanoparticles in to a visible region. These Cu:ZnS nanoparticles were employed as a photocatalyst for chemoselective synthesis of 2-substituted azoles by the reaction of benzyl bromides and 1,2-Diaminobenzene or 2-Mercaptoaniline in visible light. Analogous experiments confirmed that the reaction were proceeds through one pot C–N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence. The enhanced catalytic activity by doping could be attributed to the presence of trapping level generated by copper doping which augments the relaxation time of electron and holes so that they are easily available for the reaction. The method was also applicable for the synthesis of quinazolin-4(3H)-ones.

2-ARYLBENZIMIDAZOLES AS PPARGC1A ACTIVATORS FOR TREATING NEURODEGENERATIVE DISEASES

A genus of compounds encompassed by formula (III) and their use is disclosed: Formula (III). The compounds activate Ppargc1a and, as a consequence, are useful for treating a variety of neurodegenerative diseases such as amyotrophic lateral sclerosis (ALS), Alzheimer's disease, Parkinson's disease, Huntington's disease, frontotemporal degeneration, dementia with Lewy bodies, motor neuron diseases, and a demyelinating disease.

Sulfonated carbon-encapsulated iron nanoparticles as an efficient magnetic nanocatalyst for highly selective synthesis of benzimidazoles

Surface functionalized carbon-encapsulated iron nanoparticles (CEINs) were found to be a magnetic nanocatalyst for the efficient and highly selective synthesis of benzimidazoles. CEINs were covalently decorated with carboxyl or sulfonyl groups and their catalytic activity was examined. Carboxyl-modified CEINs were obtained via the radical or oxidative treatment, whilst the sulfonated CEINs were obtained using the one-step diazotization approach with sulfanilic acid and isoamyl nitrite. The content of surface acidic groups varied between the obtained materials and was found to be the highest for sulfonyl-modified CEINs. CEINs functionalized with sulfonyl groups were the most efficient and the most selective nanocatalyst for the synthesis of benzimidazoles. Various benzimidazoles were obtained in very high yields (92.5-97.0%). Both metallocene, aliphatic, heterocyclic and aromatic aldehydes substituted with different functional groups were subjected to the synthesis process. The reaction proceeded in a short time, which varied from 25 min to 65 min depending on the aldehyde used. Additionally, the mechanism of the studied catalytic condensation by applying sulfonated CEINs as the catalyst was discussed. Importantly, the developed magnetic nanocatalysts could be easily separated from the reaction mixture using a permanent magnet. The nanocatalysts can be used up to six reaction cycles without any significant loss of their catalytic activity. This work opens up new ways for very efficient and simple synthesis of benzimidazoles-an important class of organic compounds for various biomedical applications.