36054-00-9

Usage

Uses

Used in Pharmaceutical Synthesis:
6-Methyl-2,3-dihydroquinolin-4(1H)-one is used as an intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows for the development of new drugs with potential therapeutic effects.
Used in Agrochemical Synthesis:
In the agrochemical industry, 6-Methyl-2,3-dihydroquinolin-4(1H)-one is used as a precursor for the development of new agrochemicals, such as pesticides and herbicides, to improve crop protection and yield.
Used as an Antioxidant:
6-Methyl-2,3-dihydroquinolin-4(1H)-one is used as an antioxidant due to its ability to inhibit oxidative stress and protect cells from damage. This property makes it a potential candidate for use in various applications, such as food preservation and cosmetic formulations.
Used in Cancer Research:
6-Methyl-2,3-dihydroquinolin-4(1H)-one has shown promise in inhibiting the growth of certain cancer cell lines. It is used as a potential anticancer agent in research studies, with the aim of developing new therapeutic strategies for cancer treatment.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic outcomes of 6-Methyl-2,3-dihydroquinolin-4(1H)-one, various drug delivery systems, such as organic and metallic nanoparticles, have been developed. These systems aim to improve the compound's delivery to target cells and tissues, increasing its efficacy in treating diseases.

Upstream product

• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 833486-34-3 3-(2-amino-5-methylphenyl)-2-propyn-1-ol 
• 29289-13-2 2-iodo-4-methylaniline 
• 852292-32-1 N-[2-(3-hydroxy-prop-1-ynyl)-4-methyl-phenyl]-4-methyl-benzenesulfonamide 
• 207454-11-3 3-p-tolylaminopropionic acid ethyl ester 
• 27418-59-3 3-(p-methylphenylamino)propanoic acid 
• 106-49-0 p-toluidine 
• 21437-82-1 3-bomo-N-(4-methylphenyl)propanamide 
• 624-31-7 4-tolyl iodide 
• 38560-27-9 N-(4-methylphenyl)azetidin-2-one 
• 21911-85-3 methyl 3-(p-toluidino)propanoate 

Downstream Products

• 1274848-26-8 6-methyl-8-(p-tolylethynyl)-2,3-dihydroquinolin-4(1H)-one 
• 1274848-28-0 6-methyl-8-((3-nitrophenyl)ethynyl)-2,3-dihydroquinolin-4(1H)-one 
• 1274848-46-2 (8-methyl-5-p-tolyl-2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-1-one) 
• 1274848-49-5 8-methyl-5-(3-nitrophenyl)-2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-1-one 
• 23432-40-8 6-methyl-4(1H)-quinolinone 
• 1385731-24-7 2-methyl-10-phenylacridin-9(10H)-one 

Relevant academic research and scientific papers

Peptidomimetics and Methods of Using the Same

Disclosed herein are compounds useful for modulating the mu-opioid receptor (“MOR”) and/or delta-opioid receptor (“DOR”), and methods of using these compounds to treat diseases and conditions, such as pain. In particular, disclosed herein are compounds of

Asymmetric Synthesis of Cyclopentene-Fused Tetrahydroquinolines via N-Heterocyclic Carbene Catalyzed Domino Reactions

A new strategy for the N-heterocyclic carbene catalyzed asymmetric synthesis of cyclopentene-fused tetrahydroquinoline derivatives has been developed. The one-pot organocatalytic domino protocol allows a direct entry to the characteristic cyclopenta[ c ]tetrahydroquinoline core of many alkaloids and some potential drugs employing readily available quinolinone and enal substrates in good domino yields and stereoselectivities.

Synthesis of new tricyclic 5,6-dihydro-4H-benzo[b][1,2,4]tri-azolo[1,5-d][1,4]diazepine derivatives by [3+ + 2]-cyclo-addition/rearrangement reactions

Two new series of tricyclic heterocycles, namely 5,6-dihydro-4H-benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepinium salts 10 and the related neutral, free bases 13 were synthesized from 4-acetoxy-1-acetyl-4-phenylazo-1,2,3,4-tetrahydroquinolines 8 and nitriles 9 in the presence of aluminium chloride by the [3+ + 2]-cycloaddition reaction of the in situ generated azocarbenium intermediates 14 followed by a ring-expansion rearrangement. In the rearrangement reaction, the phenyl substituent in the initially formed spiro-triazolium adducts 16 underwent a [1,2]-migration from C(3) to the electron-deficient N(2). This led to the ring expansion from 6-membered piperidine to 7-membered diazepine furnishing the tricyclic 1,2,4-triazole-fused 1,4-benzodiazepines.

Superacid-catalyzed tandem Meyer–Schuster rearrangement/intramolecular hydroamination of o-anilinopropargyl alcohols for the synthesis of 2,3-dihydro-4(1H)-quinolones

A TfOH-catalyzed synthesis of 2,3-dihydro-4(1H)-quinolones from o-anilinopropargyl alcohols was developed. Studies of N-protecting groups and substituents in phenyl rings showed that diverse groups could be applied. By controlling the catalyst loading, o-anilinopropargyl alcohols underwent the expected transformation smoothly to produce N-protected or N-deprotected 2,3-dihydro-4 (1H)-quinolones in good yields. This transformation probably involved a tandem Meyer–Schuster rearrangement/intramolecular hydroamination reaction process.

Asymmetric Synthesis and in Vitro and in Vivo Activity of Tetrahydroquinolines Featuring a Diverse Set of Polar Substitutions at the 6 Position as Mixed-Efficacy μ Opioid Receptor/δ Opioid Receptor Ligands

We previously reported a small series of mixed-efficacy μ opioid receptor (MOR) agonist/δ opioid receptor (DOR) antagonist peptidomimetics featuring a tetrahydroquinoline scaffold and showed the promise of this series as effective analgesics after intrape

Quinolinoneacetic acid derivatives as novel glutathione S-transferase P1-1 inhibitors: Insights into the interaction modes by molecular modeling

Glutathione S-transferase P1-1 (GSTP1-1, EC 2.5.1.18) is generally conceived to be an important player in the acquired resistance of tumor to anticancer agents, thus a series of quinolinoneacetic acid derivatives were synthesized and their inhibitory effe

Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones

N-Unsubstituted β-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.

Transition metal mediated construction of pyrrole ring on 2,3-dihydroquinolin-4(1H)-one: Synthesis and pharmacological evaluation of novel tricyclic heteroarenes

A facile two-step method for the construction of fused pyrrole ring leading to 5-substituted 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-1-ones via C-C followed by intramolecular C-N bond forming reaction is described. In vitro pharmacological evaluation and

Synthesis of 2,3-dihydro-4(1H)-quinolones and the corresponding 4(1H)-quinolones via low-temperature fries rearrangement of N-arylazetidin-2- ones

N-Arylazetidin-2-ones of the general form 1, which are readily prepared by GoldbergBuchwald-type copper-catalyzed coupling of N-unsubstituted azetidin-2-ones with the relevant aryl halide or using Mitsunobu cyclization processes, undergo smooth Fries-rearrangement in triflic acid at 018°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0M aqueous sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).