64976-62-1

Usage

Uses

Used in Pharmaceutical Synthesis:
8-METHYL-5-NITROQUINOLINE is used as a key intermediate in the synthesis of various pharmaceuticals due to its antitumor, antimalarial, and antimicrobial properties. It plays a crucial role in drug discovery and development, contributing to the creation of new therapeutic agents.
Used in Agrochemical Production:
In the agrochemical industry, 8-METHYL-5-NITROQUINOLINE is utilized as a component in the development of pesticides and other crop protection products, leveraging its antimicrobial properties to enhance crop health and yield.
Used as a Fluorescent Dye in Biochemical Research:
8-METHYL-5-NITROQUINOLINE is employed as a fluorescent dye in biochemical and cellular imaging studies. Its optical properties allow researchers to visualize and track cellular processes, contributing to advancements in cell biology and related fields.
Used in Medicinal Field:
8-METHYL-5-NITROQUINOLINE is used in the medicinal field as a building block for the development of drugs with potential applications in treating various diseases, including cancer and infectious diseases, due to its demonstrated biological activities.
Used in Agricultural Field:
In the agricultural field, 8-METHYL-5-NITROQUINOLINE is used in the development of agrochemicals that protect crops from diseases and pests, thereby increasing agricultural productivity and ensuring food security.

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

Upstream product

• 611-32-5 8-methylquinoline 
• 56-81-5 glycerol 
• 99-55-8 2-methyl-5-nitroaniline 
• 107-18-6 allyl alcohol 

Downstream Products

• 50358-40-2 8-methylquinolin-5-ylamine 
• 83848-59-3 5-nitroquinoline-8-carboxylic acid 
• 80690-06-8 5-aminoquinoline-8-carboxylic acid 
• 1575701-52-8 4-methyl-N-[(5-nitroquinolin-8-yl)methyl]benzenesulfonamide 
• 1609646-67-4 N-((5-nitroquinolin-8-yl)methyl)-4-(trifluoromethyl)benzenesulfonamide 
• 1609646-84-5 N-((5-nitroquinolin-8-yl)methyl)-4-nitrobenzenesulfonamide 
• 1609646-85-6 N-((5-nitroquinolin-8-yl)methyl)-4-chlorobenzenesulfonamide 
• 1609646-86-7 N-((5-nitroquinolin-8-yl)methyl)-4-methoxybenzenesulfonamide 
• 1609646-87-8 N-((5-nitroquinolin-8-yl)methyl)-2-(trifluoromethyl)benzenesulfonamide 
• 1609646-88-9 N-((5-nitroquinolin-8-yl)methyl)-3-(trifluoromethyl)benzenesulfonamide 
• 1609646-89-0 N-((5-nitroquinolin-8-yl)methyl)-1-phenylmethanesulfonamide 
• 205046-59-9 8-cyano-5-nitroquinoline 

Relevant academic research and scientific papers

Cobalt-catalyzed ring-opening addition of azabenzonorbornadienes: Via C(sp3)-H bond activation of 8-methylquinoline

The first ring-opening addition of a benzylic C(sp3)-H bond to azabenzonorbornadienes is demonstrated. The reaction proceeded under the catalytic system of [Cp?CoI2(CO)], AgSbF6 and Fe(OAc)2 in PhOMe. The methodology showed a good substrate scope with up to 96 yield. The relative configuration of the product was determined as cis-configuration by X-ray crystallography.

IMMUNOMODULATORY COMPOUNDS

Disclosed are immunomodulatory compounds, pharmaceutical compositions containing them, and methods of making and using the compounds to treat diseases and disorders characterized by aberrant protein activity that can be targeted by cereblon.

Palladium-Catalyzed C-H Bond Functionalization Reactions Using Phosphate/Sulfonate Hypervalent Iodine Reagents

A new and operationally simple approach for palladium-catalyzed C-H functionalization reactions utilizing an organophosphorus/sulfonate hypervalent iodine reagent as both an oxidant and the source of a functional group has been developed. Through this method, the oxidative phosphorylation-, sulfonation-, and hydroxylation of unactivated benzyl C(sp3)-H bonds, along with the hydroxylation and arylation of aryl C(sp2)-H bonds, are successfully realized under mild conditions and with excellent site-selectivity. The versatile C-OSO2R bond provides a platform for a wide array of subsequent diversification reactions.

Cathepsin B inhibitors: Further exploration of the nitroxoline core

Human cathepsin B is a cysteine protease with many house-keeping functions, such as intracellular proteolysis within lysosomes. Its increased activity and expression have been strongly associated with many pathological processes, including cancers. We present here the design and synthesis of novel derivatives of nitroxoline as inhibitors of cathepsin B. These were prepared either by omitting the pyridine part, or by modifying positions 2, 7, and 8 of nitroxoline. All compounds were evaluated for their ability to inhibit endopeptidase and exopeptidase activities of cathepsin B. For the most promising inhibitors, the ability to reduce extracellular and intracellular collagen IV degradation was determined, followed by their evaluation in cell-based in vitro models of tumor invasion. The presented data show that we have further defined the structural requirements for cathepsin B inhibition by nitroxoline derivatives and provided additional knowledge that could lead to non-peptidic compounds with usefulness against tumor progression.

Cp?Rh(III)-Catalyzed Mild Addition of C(sp3)-H Bonds to α,β-Unsaturated Aldehydes and Ketones

A Rh(III)-catalyzed addition of benzylic C(sp3)-H bond to α,β-unsaturated ketones/aldehydes has been realized, leading to efficient synthesis of γ-aryl ketones/aldehydes. This atom-economic reaction proceeded under mild and redox-neutral conditions with a broad substrate scope. Besides benzylic C-H, allylic C-H bonds are also applicable when assisted by O-methyl ketoxime directing groups.

From Anilines to Quinolines: Iodide- and Silver-Mediated Aerobic Double C?H Oxidative Annulation–Aromatization

Quinoline synthesis from easily accessible raw materials such as anilines is a valuable and meaningful task. Herein, we communicate an iodide- and silver-mediated C?H/C?H oxidative annulation–aromatization between anilines and allyl alcohols. This protocol provides a direct route to the synthesis of quinoline derivatives from inexpensive commodities. Various kinds of anilines, even heterocyclic anilines, were shown to be workable substrates, generating the corresponding multi-substituted quinolines in good yields.

Rhodium(III)-catalyzed intermolecular amidation with azides via C(sp 3)-H functionalization

The amidation reactions of 8-methylquinolines with azides catalyzed by a cationic rhodium(III) complex proceed efficiently to give quinolin-8- ylmethanamine derivatives in good yields via C(sp3)-H bond activation under external oxidant-free conditions. A catalytically competent five-membered rhodacycle has been isolated and characterized, revealing a key intermediate in the catalytic cycle.

Iridium-catalyzed intermolecular amidation of sp3 C-H bonds: Late-stage functionalization of an unactivated methyl group

Reported herein is the iridium-catalyzed direct amidation of unactivated sp3 C-H bonds. With sulfonyl and acyl azides as the amino source, the amidation occurs efficiently under mild conditions over a wide range of unactivated methyl groups with high functional group tolerance. This procedure can be successfully applied for the direct introduction of an amino group into complex compounds and thus can serve as a powerful synthetic tool for late-stage C-H functionalization.

TRICYCLIC COMPOUNDS AS mPGES-1 INHIBITORS

The present disclosure is directed to compounds of formula (I), and pharmaceutically acceptable salts thereof, as m PGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (m PGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthma, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases.

8-Methylquinoline palladacycles: Stable and efficient catalysts for carbon-carbon bond formation

Cyclopalladated, phosphine free, 8-methyl quinoline based complexes (2a-j) are excellent catalysts for the Heck vinylation of aryl iodides and bromides with turnover numbers of greater than 25 million observed in some cases. The catalysts are air and moisture stable.