613-30-9

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYL-6-NITROQUINOLINE is used as a reagent for the development of potent, selective, and orally efficacious antagonists of melanin-concentrating hormone receptor 1 (MCHR1). These antagonists play a crucial role in the regulation of various physiological processes, including energy homeostasis, stress response, and feeding behavior. By targeting MCHR1, these antagonists can potentially be used in the treatment of obesity, anxiety, and other related disorders.

InChI:InChI=1/C10H8N2O2/c1-7-2-3-8-6-9(12(13)14)4-5-10(8)11-7/h2-6H,1H3

Upstream product

• 100-01-6 4-nitro-aniline 
• 123-63-7 paracetaldehyde 
• 123-73-9 crotonaldehyde 
• 123-73-9 trans-Crotonaldehyde 
• 91-63-4 2-methylquinoline 

Downstream Products

• 119062-64-5 (E)-6-nitro-2-styrylquinoline 
• 65079-19-8 2-methylquinolin-6-amine 
• 1207-81-4 4-chloro-2-methyl-6-nitroquinoline 
• 112089-59-5 methyl 6-nitroquinoline-2-carboxylate 
• 59500-67-3 6-nitroquinoline-2-carbaldehyde 
• 90767-09-2 2-(bromomethyl)-6-nitroquinoline 

Relevant academic research and scientific papers

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.

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.

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.

Preparation method of nitro-substituted quinadine

The invention belongs to the field of organic synthesis and particularly relates to a preparation method of nitro-substituted quinadine. The preparation method is realized by the following step: underthe condition of hydrochloric acid and zinc chloride catalysis, nitroaniline reacts with a crotaldehyde compound to obtain the nitro-substituted quinadine as a target object. The preparation method provided by the invention has the benefits that under the synergistic action of hydrochloric acid and zinc chloride, through controlling the amount of all reaction raw materials and the reaction time,reaction conditions are mild, the product yield is high, and the industrialization is easy; the preparation method provided by the invention is applicable to a variety of reaction substrates, therefore, a quinadine derivative combination library with a rich structure is synthesized through screening or optimizing a reactant, which is well applied to the preparation of natural products and functional materials or bioactive compounds.

Reaction of nitroanilines with aldehydes. Refinement of the Doebner–Miller reaction mechanism

Due to intramolecular hydrogen bonding between the amino and nitro groups, o-nitroaniline is incapable of forming Schiff bases in the reactions with acetaldehyde and crotonaldehyde but is converted to quinoline derivative under Doebner–Miller reaction conditions via addition to the C=C double bond of the α,β-unsaturated aldehyde. Under analogous conditions, p-nitroaniline possessing a free amino group gives rise to the product of Doebner–Miller quinoline synthesis through intermediate formation of Schiff base dimer. The reaction of p-nitroaniline with benzaldehyde also yields the corresponding Schiff base, whereas o-nitroaniline is converted to N-benzyl derivative.

Continuous Flow Doebner-Miller Reaction and Isolation Using Continuous Stirred Tank Reactors

Continuous flow Doebner-Miller synthesis of different quinaldines from respective anilines is demonstrated using sulfuric acid as a homogeneous catalyst. The extent of reaction was monitored for various parameters, namely, temperature, residence time, mole ratio of sulfuric acid to substrate, mole ratio of crotonaldehyde to substrate, and so forth. Continuous stirred reactors in series were used as a preferred configuration for this rection that generates byproduct in the form of sticky solid material. The approach has been extended for six different anilines, and the results are compared with batch reactions. Continuous stirred reactors in series with distributed dosing of crotonaldehyde facilitated a continuous flow reaction with lower byproduct formation, increased yields, and continuous workup and is a scalable approach.

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.

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.

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.

A catalyst-free benzylic C-H bond olefination of azaarenes for direct mannich-like reactions

A highly efficient synthesis of trans-alkenylazaarene under catalyst-free conditions was developed via the addition of methylazaarenes to N-sulfonyl aldimines and a subsequent C-N elimination in situ. A one-pot procedure for this addition-elimination was also developed. The reaction could tolerate a broad substrate scope and give the corresponding alkenylazaarenes in high yields.