50333-13-6

Basic information

• Product Name: 2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one
• Synonyms: 2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one;2,2,6-Trimethyl-2H-pyrano[3,2-c]quinolin-5(6H)-one;N-Methylflindersine;NSC 347659
• CAS NO: 50333-13-6
• Molecular Formula: C₁₅H₁₅NO₂
• Molecular Weight: 241.2851
• Mol File: 50333-13-6.mol
• Article Data: 23

Chemical Properties

• Melting Point: 85℃
• Boiling Point: 365.8°Cat760mmHg
• Flash Point: 175°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 1.53E-05mmHg at 25°C
• Refractive Index: 1.625
• PKA: 0.40±0.40(Predicted)
• CAS DataBase Reference: 2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one(50333-13-6)
• EPA Substance Registry System: 2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one(50333-13-6)

Safety Data

• Hazardous Substances Data: 50333-13-6(Hazardous Substances Data)

Usage

General Description

2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one, also known as TDQ or quinoline-5-one, is a chemical compound with a unique structure and a variety of potential applications. It is a heterocyclic compound that contains a pyranoquinoline core, and its distinct molecular structure gives it potential bioactive properties. TDQ has been studied for its potential pharmacological activities, including its ability to inhibit the growth of cancer cells. It has also been investigated for its potential use in organic light-emitting diodes and as a component in photodynamic therapy for the treatment of tumors. Additionally, TDQ has been explored as a potential antioxidant and anti-inflammatory agent, making it a compound of interest for further research and development.

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 
• 91421-74-8 3,4-dihydro-2,2,6-trimethyl-2H,5H-pyrano<3,2-c>quinolin-5-one 
• 15954-07-1 4-hydroxy-(3-methyl-2-butenyl)-1-methyl-2-quinolone 
• 74-88-4 methyl iodide 
• 81530-29-2 (E)-5-methylhex-2-enoic acid chloride 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 106-95-6 allyl bromide 
• 134-20-3 2-carbomethoxyaniline 
• 135033-98-6 5-methyl-N-(2'-carbomethoxyphenyl)-2-hexanamide 
• 96838-25-4 4-hydroxy-3-isobutylidene-2-oxo-2,3-dihydrofuro(2,3-b)quinoline 
• 96838-21-0 3-isobutylidene-2,4-dioxo-2,3,4,5-tetrahydrofuro(3,2-c)quinoline 

Relevant articles and documents

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

Total syntheses of pyranoquinoline alkaloids: Simulenoline, huajiaosimuline, and (±)-7-demethoxyzanthodioline

-

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.

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.

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