65079-19-8

Usage

Uses

6-Amino-2-methylquinoline is used as an organic chemical synthesis intermediate.

InChI:InChI=1/C10H10N2/c1-7-2-3-8-6-9(11)4-5-10(8)12-7/h2-6H,11H2,1H3

Upstream product

• 100-01-6 4-nitro-aniline 
• 613-30-9 2-methyl-6-nitroquinoline 
• 106-50-3 1,4-phenylenediamine 
• 103858-07-7 6-amino-2-methyl-quinoline-4-carboxylic acid 

Downstream Products

• 91875-31-9 2-methyl-6-phenylquinoline 
• 72041-93-1 N-tert-Butyl-N'-(2-methyl-quinolin-6-yl)-N''-thiazol-2-yl-guanidine 
• 36749-63-0 2,7-dimethyl-1,8-diazaphenanthrene 
• 649569-61-9 2-methyl-1,2,3,4-tetrahydro-quinolin-6-ylamine 
• 784157-40-0 N-(2-methylquinolin-6-yl)carbamic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis of 4,7-phenanthroline methyl derivatives

6-Aminoquinaldine condensation with aromatic aldehydes and cyclic β-diketones (1,3-cyclohexanedione or dimedone) in butanol afforded new 12-aryl-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-ones and their 9,9-dimethyl derivatives. 2004 MAIK "Nauka/ Interperiodica".

Discovery and Biological Evaluation of a Novel Highly Potent Selective Butyrylcholinsterase Inhibitor

To discover novel BChE inhibitors, a hierarchical virtual screening protocol followed by biochemical evaluation was applied. The most potent compound 8012-9656 (eqBChE IC50 = 0.18 ± 0.03 μM, hBChE IC50 = 0.32 ± 0.07 μM) was purchased and synthesized. It inhibited BChE in a noncompetitive manner and could occupy the binding pocket forming diverse interactions with the target. 8012-9656 was proven to be safe in vivo and in vitro and showed comparable performance in ameliorating the scopolamine-induced cognition impairment to tacrine. Additionally, treatment with 8012-9656 could almost entirely recover the Aβ1-42 (icv)-impaired cognitive function to the normal level and showed better behavioral performance than donepezil. The evaluation of the Aβ1-42 total amount confirmed its anti-amyloidogenic profile. Moreover, 8012-9656 possessed blood-brain barrier (BBB) penetrating ability, a long T1/2, and low intrinsic clearance. Hence, the novel potential BChE inhibitor 8012-9656 can be considered as a promising lead compound for further investigation of anti-AD agents.

Synthesis and biological evaluation of 2-quinolineacrylamides

A series of C6-substituted N-hydroxy-2-quinolineacrylamides (3–15), with four types of bridging groups have been synthesized. Most of these compounds exhibit antiproliferative activity against A549 and HCT116 cells and Western blot analysis revealed that they are able to inhibit HDAC. Measurement of the HDAC isoform activity of ether-containing compounds showed that compound 9 has distinct HDAC6 selectivity, more than 300-fold over other isoforms. This paper describes the development of 6-aryloxy-N-hydroxy-2-quinolineacrylamides as potential HDAC6 inhibitors.

Butyrylcholine esterase selective inhibitor and preparation method and application thereof

The invention discloses a butyrylcholine esterase selective inhibitor and a preparation method and application thereof. The invention discloses a compound shown in a formula (I), and also discloses application of the compound in preparation of medicines for preventing or treating Alzheimer's disease. An inventor uses the inhibiting activity of butyrylcholine esterase, selective screening and Morris water maze experiment as carriers to evaluate the function of the compound in the formula (I) for treating the Alzheimer's disease (especially medium and severe Alzheimer's disease), the good in-vitro and in-vivo activities and higher selectivity are found, and the compound can be further developed into a precursor substance which can selectively inhibit the butyrylcholine esterase to reach thefunction of treating the Alzheimer's disease. The formula (I) is shown in the specification.

Insight into the effects of modifying chromophores on the performance of quinoline-based dye-sensitized solar cells

A series of organic dyes based on quinoline as an electron-deficient π-linker, were designed and synthesized for dye sensitized solar cells (DSSC) application. These push-pull conjugated dyes, sharing same anchoring group with distinctive electron-rich donating groups such as N,N-diethyl (DEA-Q), 3,6-dimethoxy carbazole (CBZ-Q), bis(4-butoxyphenyl)amine (BPA-Q), were synthesized by Riley oxidation of [sbnd]CH3 followed by Knoevenagel condensation of the corresponding aldehyde precursors 2a–c with cyanoacrylic acid. The optical, electrochemical, theoretical calculation and photovoltaic properties with these three dyes were systematically investigated. Compared to DEA-Q and CBZ-Q, BPA-Q possesses better light harvesting properties with regard to extended conjugate length, red-shifted intramolecular charge transfer band absorption and broaden light-responsive IPCE spectrum, resulting in a greater short circuit photocurrent density output. BPA-Q also has improved open-circuit voltage due to the apparent large charge recombination resistance. Consequently, assembled with iodine redox electrolytes, the device with BPA-Q achieved the best overall conversion efficiency value of 3.07% among three dyes under AM 1.5G standard conditions. This present investigation demonstrates the importance of various N-substituent chromophores in the prevalent D-π-A type organic sensitizers for tuning the photovoltaic performance of their DSSCs.

Highly chemoselective reduction of azides to amines by Fe(0) nanoparticles in water at room temperature

A highly chemoselective reduction of aryl, heteroaryl, acyl and sulfonyl azides to the corresponding amines has been achieved by Fe(0) nanoparticles in water at room temperature in the absence of external hydride source. Several readily reducible functionalities including alkene, alkyne, S-S linkage, OTBDMS remain unaffected during reduction.

ANDROGEN RECEPTOR LIGANDS

Described are compounds that inhibit androgen receptor action, pharmaceutical compositions including the compounds, and methods of using the compounds and compositions for treating disorders and conditions in a subject.

Comparative studies of organic dyes with a quinazoline or quinoline chromophore as π-conjugated bridges for dye-sensitized solar cells

A new series of organic D-π-A dyes bearing either quinazoline or quinoline as the conjugated bridges in the chromophore with a diphenylamine moiety as the electron donor and a cyanoacetic acid unit as the electron acceptor, have been designed and synthesized for photoconversion in dye sensitized solar cells (DSSCs). The absorption spectra, density functional theory calculations, electrochemical and photovoltaic properties of these dyes are systematically investigated. Among the four dyes the sensitized solar cell based upon the quinoline dye bearing butoxy groups gave a short circuit photocurrent density of 7.04 mA cm-2, an open circuit voltage of 0.52 V, and a fill factor of 0.69, corresponding to an overall conversion efficiency of 2.51% using I-/I3- redox couple-based liquid electrolyte without 4-tert-butylpyridine additives under standard global AM 1.5 irradiation (100 mW cm-2). The photovoltaic performance of the dye with 4,4′-dibutoxy diphenylamine as the donor and quinoline unit as the π-bridge was higher than that of the other photosensitizers, which is mainly attributed to the higher molar extinction coefficient and broader absorption band. The experimental results demonstrate that rational molecular engineering is crucial for constructing highly efficient charge transfer sensitizers.

A quinoline based fluorescent probe that can distinguish zinc(II) from cadmium(II) in water

A new quinoline based fluorescent probe (DQ) for Zn2+ and Cd2+ has been designed and synthesized. The new probe shows quite different fluorescence response to Zn2+ and Cd2+ in aqueous solution. IR and NMR spectra demonstrated that the different response is caused by amide tautomerization of the probe molecule when coordinating with Zn2+ and Cd2+. The dissociation constants of Zn 2+ and Cd2+ complex were detected to be 3.36 and 30.62 nM, respectively. Other metal ions have no effect on the fluorescence spectrum of the probe. Thus the new probe can detect Zn2+ and Cd2+ in water with high selectivity and sensitivity.

Quinoline-based azo derivative assembly: Optical limiting property and enhancement mechanism

Abstract To further investigate the dependence of optical limiting properties on molecular structures, especially the strong intermolecular influence, such as the influences of hydrogen bond, dipole-dipole interaction and their synergetic effect on optical limiting properties, three polar D-π-A conjugated quinoline-based heterocyclic azo derivatives (3a, 3b and 3c) with different hydrogen-bond recognition abilities were designed and synthesized. Their structures and properties were characterized and evaluated by infrared spectroscopy, thermogravimetric analysis, and ultraviolet-visible spectrometry. The strengthening mechanism of optical limiting property was investigated in detail based on theoretical calculation and experimental results of molecular assembly induced by synergetic effect of hydrogen bond and dipole-dipole interaction. The results indicate that the optical limiting properties of these polar D-π-A conjugated optical materials were significantly affected by molecular structure, strong intermolecular interaction and their synergetic enhancement effect.