6340-03-0

Usage

Uses

Used in Pharmaceutical Synthesis:
1H-Benzimidazole-1-ethanol(9CI) is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its unique structure and potential biological activities.
Used in Antiviral Applications:
1H-Benzimidazole-1-ethanol(9CI) is used as an antiviral agent for its potential to inhibit viral replication and reduce the severity of viral infections.
Used in Antifungal Applications:
1H-Benzimidazole-1-ethanol(9CI) is used as an antifungal agent to combat fungal infections by disrupting the fungal cell wall and inhibiting fungal growth.
Used in Anticancer Applications:
1H-Benzimidazole-1-ethanol(9CI) is used as an anticancer agent for its potential to target and inhibit the growth of cancer cells, making it a promising candidate for the development of novel cancer therapies.
Used in Medicinal Chemistry Research:
1H-Benzimidazole-1-ethanol(9CI) is used as a valuable compound in medicinal chemistry research for its potential to contribute to the discovery and development of new drugs with diverse therapeutic applications.
Used in Drug Discovery:
1H-Benzimidazole-1-ethanol(9CI) is used in drug discovery processes to identify and optimize new drug candidates with improved efficacy, safety, and selectivity for various diseases and conditions.

InChI:InChI=1/C9H10N2O/c12-6-5-11-7-10-8-3-1-2-4-9(8)11/h1-4,7,12H,5-6H2

Upstream product

• 75-21-8 oxirane 
• 51-17-2 benzoimidazole 
• 107-07-3 2-chloro-ethanol 
• 96-49-1 [1,3]-dioxolan-2-one 
• 95-54-5 1,2-diamino-benzene 
• 624-76-0 Iodoethanol 
• 64-18-6 formic acid 
• 4926-58-3 2-((2-hydroxyethyl)amino)aniline 
• 540-51-2 2-bromoethanol 
• 40332-16-9 2-(1H-benzo[d]imidazol-1-yl)acetic acid 
• 118482-18-1 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-benzimidazole 

Downstream Products

• 22492-19-9 1-(2-chloroethyl)-1H-benzo[d]imidazole 
• 1013022-33-7 1-(2-(2-methyl-4-nitro-1H-imidazol-1-yl)ethyl)-1H-benzo[d]imidazole 
• 39936-67-9 1,3-bis(2-hydroxyethyl)-1H-benzo[d]imidazol-2(3H)-one 
• 1562526-63-9 2-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-6-(benzyloxy)-4-(benzyloxymethyl)-1,2,4-triazine-3,5(2H,4H)-dione 
• 1562526-60-6 2-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-4-(benzyloxymethyl)-6-bromo-1,2,4-triazine-3,5(2H,4H)-dione 

Relevant academic research and scientific papers

Synthesis, crystal structures, spectral investigations, conformational analysis and DFT studies of N- heterocyclic carbene precursors

Three new 2-hydroxyethyl substituted N-heterocyclic carbene (NHC) precursors were synthesized in this study. These NHC precursors were prepared from 1-(alkyl/aryl)benzimidazole and alkyl halides. Their structural characterizations were performed by elemental analysis, 1H NMR, 13C NMR, FT–IR and UV–Vis spectroscopy and single-crystal X-ray diffraction. The spectral features were also characterized by Density Functional Theory (DFT) at B3LYP/Lanl2dz//6-31G++(d,p) basis set. Two most stable conformers belonging to the compounds were found by potential energy surface (PES) scan, and the theoretical ground-state geometries were investigated. Among these conformers, the geometry of the conformer-I for all compounds matches almost well with the experimental results. 1H and 13C NMR chemical shifts were calculated with GIAO approach and compared to the observed ones. Detailed vibrational assignments of the wavenumbers of the conformers were carried out based on the potential energy distribution (PED). Natural bond orbital (NBO) analysis was used to analyze the stability of the molecules arising from hyperconjugative interactions and charge delocalization. The HOMO–LUMO energy gap of the stable conformers was calculated for comparing their chemical reactivity behavior. Molecular electrostatic potential (MEP) diagrams were used to get information about ?the size, shape, charge density distribution and site of chemical reactivity of each stable conformer. The 3D Hirshfeld surfaces and the associated 2D fingerprint plots were also carried out to obtain an insight into the behavior of the interactions in the compounds.

N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates

Abstract: The reactions of imidazoles with a series of dialkyl and alkylene carbonatesafforded the corresponding N-alkyl- andN-(hydroxyalkyl)imidazoles with highyields. The reactivity of dialkyl carbonates decreases in the series dimethyl> diethyl > dibutyl carbonate. Ethylene carbonate is a more efficientalkylating agent than trimethylene carbonate. The mechanisms of alkylation ofimidazole with dimethyl carbonate and ethylene carbonate were studied by DFTquantum chemical calculations at the B3LYP/6-311++G(d,p) level of theory.

Synthesis of N-heterocyclic nitrenium (NHN) ions and related donor systems: Coordination with d10-metal ions

The synthesis of three new NNN- and CNC type N-heterocyclic nitrenium (NHN) ion based pincer ligands is reported from 1,3-di-(2′-bromoethyl)-triazolium bromide (5). The reaction of 5 with ammonium hexafluorophosphate followed by two equivalent of pyrrolid

Influence of supramolecular layer-crosslinked structure on stability of dual pH-Responsive polymer nanoparticles for doxorubicin delivery

Undesired physiological instability remains a major limitation for nanoparticle-based drug delivery. To overcome this issue, a dual pH-responsive supramolecular layer-crosslinked nanoparticles (PCB-b-PCD/PBM-b-PDPA NPs, PDM NPs), which consisted of pH-responsive hydrophobic poly(diisopropylethyl methacrylate) (pKa ≈6.3) as the core, hydrophilic poly((methacrylic acid betaine) methyl methacrylate) as the shell and pH-responsive supramolecular crosslinked layer based on β-cyclodextrin and benzimidazole (pKa 6.0), was prepared. Effects of this supramolecular layer-crosslinked structure on dilution and stored stability, protein adsorption, and pH-responsibility were investigated. PDM NPs exhibited lower critical aggregation concentrations, good unimodal distribution and better dilution stability in comparison with non-crosslinked PCB-PDPA NPs. Moreover this pH-responsive supramolecular layer-crosslinked structure did not only influence the anti-protein adsorption ability, but also reduced the disintegrated pH (from 6.3 to below 6.0) of PDM NPs, which leads to the DOX was released from PDM NPs at the mildly acid condition effectively and sustainably in vitro. Therefore, this pH-responsive layer-crosslinked NPs held promising potentials as a smart nanocarriers for drug delivery.

A2 ADENOSINE RECEPTOR AGONISTS

Disclosed are AZB adenosine receptor (AR) agonists of formula (I), in which R1, R2, R3, R4, Z, and n are defined herein. The invention also provides compositions comprising at least one compound of formula I and methods of use thereof, for example, in the treatment of septic shock, cystic fibrosis, restenosis, erectile dysfunction, inflammation, myocardial ischemia, and reperfusion injury.

Structure-activity relationships of 2,N6,5′-substituted adenosine derivatives with potent activity at the A2B adenosine receptor

2, N6, and 5′-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A2BAR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N6-ethyl or N6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-(3-(indolyl)- ethyloxy)adenosine series. Indole 5″- or 6″-halo substitution was favored at the A2BAR, but a 5′-N-ethylcarboxyamide did not further enhance potency. 2-(3″-(6″-Bromoindolyl)ethyloxy)adenosine 28 displayed an A2BAR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5′-N- ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A 2B and A2AARs and a low efficacy partial agonist at A 1 and A3ARs. Thus, we have identified and optimized 2-(2-arylethyl)oxo moieties in AR agonists that enhance A2BAR potency and selectivity.

Synthesis and aqueous chemistry of α-acetoxy-N-nitrosomorpholine: Reactive intermediates and products

α-Acetoxy-N-nitrosomorpholine (7) has been synthesized starting by the anodic oxidation of N-acetylmorpholine in methanol. The 55% yield of N-nitrosomorpholinic acid, after cyanide-for-methoxy group exchange and hydrolysis, is an improvement of ～10-fold over our original 10-step method, and this is readily converted to 7. A study of the kinetics of decomposition of 7 in aqueous media at 25 °C and 1 M ionic strength was conducted over the pH range from 1 to 12. The reaction exhibited good first-order kinetics at all values of pH, and a plot of the log of k0, the buffer-independent rate constant for decomposition, against pH indicated that a pH-independent reaction dominates in the neutral pH region whereas acid- and base-catalyzed reactions dominate in the low and high pH regions, respectively. Reaction at neutral pH in the presence of increasing concentrations of acetate ion results in a decrease in the value of kobsd, to an apparent limiting value consistent with a common-ion inhibition by the capture, and competing base-catalyzed hydration of, an N-nitrosiminium ion intermediate The 100-fold smaller reactivity of 7 at neutral pH compared with its carbon analogue, α-acetoxy-N-nitrosopiperidine, is also consistent with the electronic effects expected for such a reaction. The dinitrophenylhydrazones derived from pH-independent and acid-catalyzed reactions are identical in kind and quantity, within experimental error, to those observed in the decay of α-hydroxy-N-nitrosomorpholine. Decay of 7 in the presence of benzimidazole buffer results in the formation of 2-(2-(1H-benzo[d]imidazol-1-yl)ethoxy) acetaldehyde (12) and 2-(1H-benzo[d]imidazol-1-yl)ethanol (13). Independent synthesis and study of 12 indicates that it is stable at 80 °C in 0.1 M DCl, but it slowly decomposes to 13 in neutral and basic media in a reaction that is stimulated by primary and secondary amines, but not by tertiary amines and carbonate buffer. The benzimidazole trapping studies and those of the stability of 12 indicate the possibility that metabolic activation of N-nitrosomorpholine by hydroxylation α to the nitroso nitrogen can result in the deposition of a metastable ethoxyacetaldehyde adduct on the heteroatoms of DNA.

6-beta(substituted)-(S)-hydroxymethylpenicillanic acids and derivatives thereof

Antibacterial penicillins of the formula STR1 or a pharmaceutically acceptable salt thereof wherein R1 is a heterocyclic group and R is hydrogen, the residue of certian carboxy protecting groups or the residue of an ester group readily hydrolyzable in vivo having activity against resistant organisms.