4926-58-3

Usage

Uses

Used in Pharmaceutical Industry:
2-[(2-Aminophenyl)amino]ethanol hydrochloride is used as a key intermediate in the synthesis of antihistamines, sympathomimetic drugs, and antiarrhythmic agents. Its chemical structure allows for the creation of compounds that can target specific receptors and pathways in the body, leading to the development of effective medications for various conditions.
Used in Cardiovascular Disease Treatment:
2-[(2-Aminophenyl)amino]ethanol hydrochloride has been studied for its potential applications in the treatment of cardiovascular diseases. Its ability to interact with certain biological targets may contribute to the regulation of heart function and the improvement of blood circulation, making it a promising candidate for further research and development in this field.
Used in Antioxidant Formulations:
As an antioxidant, 2-[(2-Aminophenyl)amino]ethanol hydrochloride can help protect cells from damage caused by reactive oxygen species. It is used in the development of antioxidant formulations that can be incorporated into dietary supplements or pharmaceutical products to support overall health and well-being.
Used in Research and Development:
2-[(2-Aminophenyl)amino]ethanol hydrochloride is also used in research settings, where it serves as a valuable compound for studying the mechanisms of action of various drugs and exploring new therapeutic possibilities. Its presence in the synthesis of biologically active compounds makes it an essential tool for scientists working in the fields of chemistry, biology, and medicine.

InChI:InChI=1/C8H12N2O/c9-7-3-1-2-4-8(7)10-5-6-11/h1-4,10-11H,5-6,9H2

Upstream product

• 75-21-8 oxirane 
• 95-54-5 1,2-diamino-benzene 
• 1493-27-2 ortho-nitrofluorobenzene 
• 4926-55-0 2-[(2-nitrophenyl)amino]ethanol 
• 88-73-3 2-Chloronitrobenzene 
• 577-19-5 2-nitrophenyl bromide 

Downstream Products

• 108717-77-7 2-[2-(3-nitro-phenyl)-benzoimidazol-1-yl]-ethanol 
• 4946-08-1 2-(2-methyl-1H-benzo[d]imidazol-1-yl)-ethanol 
• 51215-27-1 2-(2-ethyl-benzimidazol-1-yl)-ethanol 
• 6340-03-0 2-(1H-benzo[d]imidazol-1-yl)ethanol 
• 102000-86-2 2-[2-(hydroxymethyl)-1H-benzimidazol-1-yl]ethanol 
• 130907-43-6 3-(4-chloro-phenyl)-1-(2-hydroxy-ethyl)-quinoxalinium; chloride 
• 115213-55-3 2-methyl-1,2,3,4-tetrahydro-benz[4,5]imidazo[1,2-a]pyrazine 
• 109569-51-9 2-benzyl-2-methyl-1,2,3,4-tetrahydro-benz[4,5]imidazo[1,2-a]pyrazinium; chloride 
• 1204501-28-9 C₂₄H₂₆N₄O₄ 
• 24134-25-6 2-(2-amino-1H-benzo[d]imidazole-1-yl)ethan-1-ol 
• 15800-90-5 10-(2-hydroxyethyl)isoalloxazine 
• 60078-53-7 1-(2-hydroxyethyl)-2-(methylamino)-1H-benzimidazole 
• 101288-63-5 2-(3-phenyl-3,4-dihydro-2H-quinoxalin-1-yl)-ethanol 
• 91-19-0 2,3-diethynylquinoxaline 

Relevant academic research and scientific papers

Discovery and development of 2-aminobenzimidazoles as potent antimalarials

The emergence of Plasmodium falciparum resistance to frontline antimalarials, including artemisinin combination therapies, highlights the need for new molecules that act via novel mechanisms of action. Herein, we report the design, synthesis and antimalarial activity of a series of 2-aminobenzimidazoles, featuring a phenol moiety that is crucial to the pharmacophore. Two potent molecules exhibited IC50 values against P. falciparum 3D7 strain of 42 ± 4 (3c) and 43 ± 2 nM (3g), and high potency against strains resistant to chloroquine (Dd2), artemisinin (Cam3.IIC580Y) and PfATP4 inhibitors (SJ557733), while demonstrating no cytotoxicity against human cells (HEK293, IC50 > 50 μM). The most potent molecule, possessing a 4,5-dimethyl substituted phenol (3r) displayed an IC50 value of 6.4 ± 0.5 nM against P. falciparum 3D7, representing a 12-fold increase in activity from the parent molecule. The 2-aminobenzimidazoles containing a N1-substituted phenol represent a new class of molecules that have high potency in vitro against P. falciparum malaria and low cytotoxicity. They possessed attractive pharmaceutical properties, including low molecular weight, high ligand efficiency, high solubility, synthetic tractability and low in vitro clearance in human liver microsomes.

Discovery of dihydropyrazino-benzimidazole derivatives as metabotropic glutamate receptor-2 (mGluR2) positive allosteric modulators (PAMs)

A scaffold hopping strategy converted the known 1-[(1-methyl-1H-imidazol-2-yl)methyl]-4-phenylpiperidine core (1 and 2) by cyclization to a fused [6 + 5+6] membered heterocyclic mGluR2 PAM scaffold. Pharmacophore guided structure?activity relationship (SAR) studies resulted in a series of potent and metabolically stable mGluR2 PAMs. A representative optimized compound (95) having the most balanced profile, demonstrated efficacy in the PCP-induced hyper-locomotion model in mice that revealed the new chemotype being a promising PAM lead targeting mGluR2 receptors and providing support for further translational studies.

A green and practical reduction of N-(4-chlorophenyl)-2-nitroaniline and its derivatives to corresponding N-substituted-benzene-1,2-diamines using thiourea dioxide

A new effective approach for synthesizing diverse N-substituted-benzene-1,2-diamines is reported. The treatment of N-substituted-2-nitroanilines with thiourea dioxide in the presence of sodium hydroxide efficiently formed the corresponding N-substituted-benzene-1,2-diamines, including N-(4-chlorophenyl)benzene-1,2-diamine with a good yield of 94%. The by-product is environmentally-friendly urea and is easy to separate from the product by filtration procedure that enhances the convenience of the approach.

Regulating Cofactor Balance In Vivo with a Synthetic Flavin Analogue

A novel strategy to regulate cofactor balance in vivo for whole-cell biotransformation using a synthetic flavin analogue is reported. High efficiency, easy operation, and good applicability were observed for this system. Confocal laser scanning microscopy was employed to verify that the synthetic flavin analogue can directly permeate into Escherichia coli cells without modifying the cell membrane. This work provides a promising intracellular redox regulatory approach to construct more efficient cell factories.

CHEMICAL REGENERATION METHOD OF OXIDIZED COENZYME NAD (P)+

It discloses a chemical regeneration method of oxidized coenzyme NAD(P)+ which is under an oxygen or air atmosphere condition, adding a catalytic amount of bridged flavin, and oxidizing NAD(P)H to obtain NAD(P)+. The catalyst for regeneration of cofactor is cheap and easily available small organic molecule having no noble metal; this regeneration system can regenerate NADH and NADPH; this regeneration system has a wide pH range and temperature range, being applicable to various oxidation reactions catalyzed by nicotinamide-dependent oxidoreductase.

"All-water" one-pot diverse synthesis of 1,2-disubstituted benzimidazoles: Hydrogen bond driven 'synergistic electrophile-nucleophile dual activation' by water

A new "all-water" tandem arylaminoarylation/arylaminoalkylation- reduction-cyclisation route is reported for one-pot diversity oriented synthesis of regiodefined 1,2-disubstituted benzimidazoles. Water plays a crucial and indispensable role through hydrogen bond driven 'synergistic electrophile-nucleophile dual activation' in the formation of N-mono-aryl/aryl alkyl/alkyl/cycloalkyl o-nitroanilines under metal and base-free conditions to replace the transition metal-based C-N bond formation (aryl amination) chemistry and underlines the origin of regiodefined installation of the diverse selection of aryl, aryl alkyl, and alkyl/cycloalkyl groups as substituents on the benzimidazole scaffold to form the 1,2-disubstituted benzimidazoles. The influence of the hydrogen bond effect of water in promoting the arylaminoarylation reaction under base and metal-free conditions has been realized through observation of inferior yields in D2O compared to that obtained in water during the reaction of o-fluoronitrobenzene with aniline separately performed in water and D2O under similar experimental conditions. Water also provides assistance in promoting the subsequent nitro reduction and in the final cyclocondensation steps. The role of water in promoting the cyclocondensation reaction through hydrogen bonds is realized by the differential product yields during the reaction of mono-N-phenyl-o- phenylenediamine with benzaldehyde performed separately in water and D 2O. The better hydrogen bond donor and hydrogen bond acceptor abilities of water compared to those of the organic solvents are the contributing/deciding factors for making the new water-assisted tandem arylaminoarylation/arylaminoalkylation-reduction-cyclisation strategy for the diversified synthesis of the regiodefined 1,2-disubstituted benzimidazoles effective in an aqueous medium, making it represent a true "all-water chemistry."

Preparation of substituted 1,2,3,4-tetrahydroquinoxalines and 2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepines from catalytic Cp*Ir hydrogen transfer N-heterocyclization of anilino alcohols

The [Cp*IrCl2]2/K2CO3 catalyzed hydrogen transfer N-heterocyclization on a series of anilino alcohols has been investigated. The catalyst (20% loading) converts anilino alcohols to 1,2,3,4-tetrahydroquinoxalines and 2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepines in 30-84% isolated yield.

Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors

A series of 3-anilino-quinoxalinones has been identified as a new class of glycogen phosphorylase inhibitors. The lead compound 1 was identified through high throughput screening as well as through pharmacophore-based electronic screening. Modifications were made to the scaffold of 1 to produce novel analogues, some of which are 25 times more potent than the lead compound.

N1,N10-Ethylene-bridged high-potential flavins: Synthesis, characterization, and reactivity

N1,N10-Ethyleneisoalloxazinium chloride and its 8-Cl-, 7-CF3-, and 3-CH3-7-CF3-substituted analogs were synthesized for the purpose of exhibiting thermal reactivity with organic substrates. The new flavins were characterized spectroscopically and electrochemically, and were found to react with amines, thiols, and phenylhydrazine, the latter case exhibiting catalytic aerobic recycling. Reactions of aliphatic benzylic and cyclopropyl amines with the 7-CF3 analog were also compared to their oxidations by tris(phenanthroline)iron(III). All reactions of the flavinium salts appear to occur through heterolytic rather than homolytic mechanisms.

Synthesis of 2-imidazolidinylidenepropanedinitrile derivatives as stimulators of gastrointestinal motility. 1

Ranitidine (1), the histamine H2-receptor antagonist, has been previously reported to increase gastric emptying and gastric motility by inhibition of acetylcholinesterase (AChE) and enhancement of acetylcholine (ACh) release. In order to obtain potent gastroprokinetic agents, a new series of ranitidine derivatives (5-32) possessing a nitrogen atom instead of a sulfur atom (B) was synthesized and their AChE inhibitory activity and potentiating action on electrically evoked contractions of guinea pig ileum were evaluated. Modification of substituents R1 and R2 markedly influenced the activities. In particular, compound 19, {1-[2-[[[5-(piperidinomethyl)-2- furanyl]methyl]amino]-ethyl]-2-imidazolidinylidene}propanedinitrile fumarate, showed 20 and 100 times more potent AChE inhibitory activity and potentiating action on the ileal contraction, respectively, than ranitidine. Furthermore, compound 19 (KW-5092) enhanced gastrointestinal motility in anesthetized rabbits along with a negligible histamine H2-receptor blocking activity.