179898-22-7

Usage

Derived from

Quinoline

Uses

Antioxidant and stabilizer in the food industry
+ Prevents oxidation of food products, extending shelf life and preserving color and flavor
+ Used in the production of rubber and plastics to prevent degradation from heat and oxygen exposure

Pharmaceutical potential

Possible treatment for conditions such as Alzheimer's disease and as an anti-inflammatory agent

Upstream product

• 591-27-5 m-Hydroxyaniline 
• 74-99-7 prop-1-yne 
• 179897-97-3 1,2-dihydro-2,2,4-trimethyl-7-(1,1,1-trimethylacetoxy)quinoline 
• 67-64-1 acetone 
• 1810-74-8 7-methoxy-2,2,4-trimethyl-1,2-dihydroquinoline 
• 536-90-3 m-Anisidine 

Downstream Products

• 179898-71-6 2-bromo-N-(2-methyl-2-propenyl)-5-nitroaniline 
• 91-22-5 quinoline 
• 179899-10-6 (R/S)-1,2,3,4-Tetrahydro-4-methyl-7-methoxyquinoline 
• 179899-02-6 (R/S)-3-ethyl-1,2,3,4-tetrahydro-2,2-dimethyl-4-quinolinone 
• 580-19-8 quinolin-7-ylamine 
• 41148-72-5 2,2,4-trimethyl-1,2-dihydro-quinolin-7-ylamine 
• 18791-99-6 4-bromo-2-thiophenecarbonitrile 
• 179898-00-1 1-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-4-quinolinone 
• 1441383-55-6 C₄₈H₃₇F₂₆N₂O₃⁽¹⁺⁾*Cl^(1-) 

Relevant academic research and scientific papers

Real time observation of microwave-enhanced reactions via fast FTIR spectroscopy

Microwave-enhanced reactions are very fast in comparison to thermal reactions. The determination of optimal end point often fails because conventional analytical methods are too slow. Therefore, we established a fast method using FTIR spectroscopy. The re

NEAR-INFRARED NERVE-SPARING FLUOROPHORES

Provided are far red to near-infrared nerve-sparing fluorescent compounds, compositions comprising them, and methods of their use in medical procedures.

ASYMMETRIC RHODAMINE DYE AND USE THEREOF IN BIOLOGICAL ASSAYS

The present disclosure relates to N-protected NH-rhodamine dyes and their use in nucleic acid detection. In particular, the disclosure relates to methods of making N-protected NH-rhodamine dyes, and methods of use of N-protected NH-rhodamine dyes (e.g., human identification). Certain dyes provided herein have unique spectral properties that complement those in existing dye sets and can be used to expand the number of reporter dyes that can be included for HID applications and other biological assays. Those fluorescent compounds are useful to label synthetic oligonucleotides. Formula (I).

NERVE-SPECIFIC FLUOROPHORE FORMULATIONS FOR DIRECT AND SYSTEMIC ADMINISTRATION

Nerve-specific fluorophore formulations for direct or systemic administration are described. The formulations can be used in fluorescence-guided surgery (FGS) to aid in nerve preservation during surgical interventions.

Rhodamine F: A novel class of fluorous ponytailed dyes for bioconjugation

Incorporation of fluorous ponytails such as polyfluorinated alkyl residues (CH2)m(CF2)nCF3 leads to a novel class of bright rhodamine-based fluorescence dyes. These dyes combine the excellent photophysical properties of the frequently used rhodamine dyes with the unique features of "light" fluorous molecules. One of those features is the possibility to separate substances utilizing fluorous solid-phase extraction (F-SPE), which is based on the specific intermolecular interaction between fluorous compounds. Thus, molecules, which are labeled with these new dyes, are not only accessible to fluorescence experiments, but can also be easily purified (via so-called FluoroFlash columns) prior to use. The dyes were bound to a cell penetrating peptoid (polycationic oligo(N-substituted) glycine) on solid supports. These conjugates were purified with F-SPE before their photophysical and biological properties were investigated. The Royal Society of Chemistry 2013.

Antitrypanosomal activity of 1,2-dihydroquinolin-6-ols and their ester derivatives

The current chemotherapy for second stage human African trypanosomiasis is unsatisfactory. A synthetic optimization study based on the lead antitrypanosomal compound 1,2-dihydro-2,2,4-trimethylquinolin-6-yl 3,5-dimethoxybenzoate (TDR20364, 1a) was undertaken in an attempt to discover new trypanocides with potent in vivo activity. While 6-ether derivatives were less active than the lead compound, several N1-substituted derivatives displayed nanomolar IC50 values against T. b. rhodesiense STIB900 in vitro, with selectivity indexes up to > 18000. 1-Benzyl-1,2-dihydro-2,2,4- trimethylquinolin-6-yl acetate (10a) displayed an IC50 value of 0.014 μM against these parasites and a selectivity index of 1700. Intraperitoneal administration of 10a at 50 (mg/kg)/day for 4 days caused a promising prolongation of lifespan in T. b. brucei STIB795-infected mice (>14 days vs 7.75 days for untreated controls). Reactive oxygen species were produced when T. b. brucei were exposed to 10a in vitro, implicating oxidative stress in the trypanocidal mode of action of these 1,2-dihydroquinoline derivatives.

Scope and mechanistic study of the ruthenium-catalyzed ortho-C-H bond activation and cyclization reactions of arylamines with terminal alkynes

The cationic ruthenium hydride complex [(PCy3) 2(CO)(CH3CN)2RuH]+BF 4- was found to be a highly effective catalyst for the C-H bond activation reaction of arylamines and terminal alkynes. The regioselective catalytic synthesis of substituted quinoline and quinoxaline derivatives was achieved from the ortho-C-H bond activation reaction of arylamines and terminal alkynes by using the catalyst Ru3-(CO)12/HBF 4·OEt2. The normal isotope effect (k CH/kCD = 2.5) was observed for the reaction of C 6H5NH2 and C6D5NH 2 with propyne. A highly negative Hammett value (ρ = -4.4) was obtained from the correlation of the relative rates from a series of meta-substituted anilines, m-XC6H4NH2, with σp in the presence of Ru3(CO)12/ HBF4·OEt2 (3 mol % Ru, 1:3 molar ratio). The deuterium labeling studies from the reactions of both indoline and acyclic arylamines with DC≡CPh showed that the alkyne C-H bond activation step is reversible. The crossover experiment from the reaction of 1-(2-amino-1-phenyl)pyrrole with DC≡CPh and HC≡CC6H4-p-OMe led to preferential deuterium incorporation to the phenyl-substituted quinoline product. A mechanism involving rate-determining ortho-C-H bond activation and intramolecular C-N bond formation steps via an unsaturated cationic ruthenium acetylide complex has been proposed.

STEROID RECEPTOR MODULATOR COMPOUNDS AND METHODS

Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.

STEROID RECEPTOR MODULATOR COMPOUNDS AND METHODS

Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.

Steroid receptor modulator compounds and methods

Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.