50333-13-6

Usage

Uses

Used in Pharmaceutical Applications:
2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one is used as a potential anticancer agent for its ability to inhibit the growth of cancer cells. Its pharmacological activities have been studied, indicating its potential to be developed into a therapeutic agent for the treatment of various types of cancer.
Used in Organic Light-Emitting Diodes (OLEDs):
In the field of materials science, 2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one is used as a component in the development of organic light-emitting diodes. Its unique structure contributes to the performance and efficiency of these devices, making it a valuable material for OLED technology.
Used in Photodynamic Therapy:
2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one is utilized as a component in photodynamic therapy for the treatment of tumors. Its potential use in this medical procedure highlights its versatility and the possibility of enhancing cancer treatment options.
Used as an Antioxidant and Anti-Inflammatory Agent:
In the realm of health and wellness, 2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one is explored for its potential antioxidant and anti-inflammatory properties. These characteristics make it a promising candidate for further research and development in the creation of novel health supplements or treatments.

InChI:InChI=1/C15H15NO2/c1-15(2)9-8-11-13(18-15)10-6-4-5-7-12(10)16(3)14(11)17/h4-9H,1-3H3

Upstream product

• 1677-46-9 4-hydroxy-1-methyl-2(1H)-quinolone 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 115-18-4 2-methyl-3-buten-2-ol 
• 144691-90-7 4-acetoxy-3-iodo-1-methyl-1,2-dihydroquinolin-2-one 
• 523-64-8 flindersine 
• 74-88-4 methyl iodide 
• 91421-74-8 3,4-dihydro-2,2,6-trimethyl-2H,5H-pyrano<3,2-c>quinolin-5-one 
• 144691-89-4 (E)-4-acetoxy-1-methyl-3-(3'-methyl-3'-hydroxybut-1'-enyl)-1,2-dihydroquinolin-2-one 
• 15954-07-1 4-hydroxy-(3-methyl-2-butenyl)-1-methyl-2-quinolone 
• 32606-02-3 4-hydroxy-1,3-dimethyl-2(1H)-quinolone 
• 541-47-9 3-Methylbutenoic acid 
• 98751-17-8 4-hydroxy-3-iodo-1-methyl-1,2-dihydroquinolin-2-one 
• 109573-22-0 4-hydroxy-N-methyl-3-(3-methylbut-3-enyl)quinolin-2(1H)-one 
• 106-95-6 allyl bromide 

Relevant academic research and scientific papers

One-Pot Preparation of Pyranoquinolinones by Ytterbium(III) Trifluoromethanesulfonate-Catalyzed Reactions: Efficient Synthesis of Flindersine, N-Methylflindersine, and Zanthosimuline Natural Products

An efficient synthesis of pyranoquinolinones is achieved by ytterbium(III) triflate-catalyzed reaction of 4-hydroxy-2-quinolones with a variety of α,β-unsaturated aldehydes in moderate yields. This new method has been applied to the synthesis of pyranoqui

A DIELS-ALDER ADDUCCT OF N-METHYLFLINDERSINE AND A QUINOLONE QUINONE METHIDE

A quinolone quinone methide (5; R=Me), prepared from 1,3-dimethyl-4-hydroxy-2-quinolone (7) and DDQ, reacted readily with N-methylflindersine (3) to give a single cyclo-addition product (4).

Efficient synthesis of substituted pyranoquinolinones from 2,4-dihydroxyquinoline: Total synthesis of zanthosimuline, cis-3′, 4′-dihydroxy-3′,4′-dihydroflindersine, and orixalone D

A convenient and efficient synthesis of pyranoquinolinones was achieved using the ethylenediamine diacetate catalyzed reactions of 2,4- dihydroxyquinoline and a variety of α,β-unsaturated aldehydes in good yield. The key feature of these reactions is the

Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1) along with nine previously known alkaloids 2-10. In addition, six semi-synthetic derivatives 3a-c, 4b, 5a and 6a were prepared by allylation and acetonidation of soyauxinium nitrate (5), edulinine (3), ribalinine (4) and arborinine (6). The structures and spectroscopic data of five of them are reported herein for the first time. The suggested mechanism for the formation of the new N-allylindolopyridoquinazoline 5a is presented. The structures of natural and derived compounds were determined employing extensive NMR and MS techniques. The absolute configuration of stereogenic centers in compounds 2-4 were determined using NOESY technique and confirmed by the single-crystal X-ray diffraction (SC-XRD) technique. The use of SC-XRD further enabled us to carry out a structural revision of soyauxinium chloride recently isolated from the same plant to soyauxinium nitrate (5). The TAE, fractions, compounds 1-7 and 9, and semi-synthetic derivatives 3a-c, 4b, 5a and 6a were evaluated for their cyto-toxic activity towards the cervix carcinoma cell line KB-3-1. No significant activity was recorded for most of the compounds except for 9, which showed moderate activity against the tested cancer cell lines.

Asymmetric Total Synthesis and Biological Evaluation of the Natural PDE4 Inhibitor Toddacoumalone

We describe herein the first asymmetric total synthesis and biological evaluation of the natural PDE4 inhibitor toddacoumalone and its stereoisomers. The key step of the total synthesis is a formal asymmetric [4 + 2] cycloaddition reaction catalyzed by chiral secondary amine catalysts. A variety of pyranoquinolinones and 3-methylcrotonaldehyde are well tolerated under the optimized reaction conditions, which paved the way for further SAR studies. Further biological evaluation showed 1a′ with the best PDE4 inhibitory activity (IC50 = 0.18 μM).

Euodenine A: A small-molecule agonist of human TLR4

A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-κB reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-α, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.

Microwave-assisted solvent and catalyst free synthesis of 2H-Pyrans

This paper describes a simple and efficient method involving domino Knovenegal/6π electrocyclization for the preparation of a variety of 2H-pyrans using microwave irradiation under solvent- and catalyst-free conditions. This method offers the advantages of a green approach, high yields, and short reaction times. Sixteen compounds (9a-p) were obtained in good to excellent yields using the procedure.

Green one-pot synthesis of 2h-pyrans under solvent-free conditions catalyzed by ethylenediammonium diacetate

Ethylenediammonium diacetate readily catalyzes the Knoevenagel-type condensation between 1,3-dicarbonyl substrates and ,-unsaturated aldehydes at room temperature under solvent-free conditions. This rapid, efficient, and convenient one-pot approach to the

Synthesis of melicodenines C, D and e

A synthesis of the unusual cyclobutane-quinolinone alkaloids melicodenines C, D and E by intermolecular [2+2] cycloaddition is described.

Environmentally benign, one-pot synthesis of pyrans by domino Knoevenagel/6π-electrocyclization in water and application to natural products

In water medium, environmentally benign, facile, and efficient synthesis of pyrans was achieved in good yields by the reactions of a variety of cyclic 1,3-dicarbonyls with several α,β-unsaturated aldehydes. The key strategy was a formal [3+3] cycloaddition by domino Knoevenagel/6π- electrocyclization. This methodology was applied to the synthesis of biologically interesting pyranocoumarin, pyranoquinolinone, and pyranonaphthoquinone derivatives along with selected natural and non-natural products. The Royal Society of Chemistry 2010.