523-64-8

Basic information

• Product Name: FLINDERSINE
• Synonyms: 2,2'-Dimethyl-a-pyrano(5',6',3,4)-2(1H)-quinolone; 2,6-Dihydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one; 2H-pyrano[3,2-c]quinolin-5-ol, 2,2-dimethyl-; 5H-pyrano[3,2-c]quinolin-5-one, 2,6-dihydro-2,2-dimethyl-
• CAS NO: 523-64-8
• Molecular Formula: C14H13NO2
• Molecular Weight: 227.262
• Product Categories: Anthraquinones, Hydroquinones and Quinones
• Mol File: 523-64-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 185-186 °C (decomp)(Solv: methanol (67-56-1))
• Boiling Point: 441°C at 760 mmHg
• Flash Point: 220.5°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 5.63E-08mmHg at 25°C
• Refractive Index: 1.631
• PKA: 12.61±0.40(Predicted)
• CAS DataBase Reference: FLINDERSINE(CAS DataBase Reference)
• NIST Chemistry Reference: FLINDERSINE(523-64-8)
• EPA Substance Registry System: FLINDERSINE(523-64-8)

Safety Data

• Hazardous Substances Data: 523-64-8(Hazardous Substances Data)

Usage

General Description

Flindersine is a chemical compound isolated from the plant Flindersia acuminata, and belongs to the class of phytochemicals known as limonoids. It has been found to possess various biological activities, including cytotoxic, anti-inflammatory, and anti-malarial properties. Flindersine has demonstrated potential as a natural product for drug development, particularly in the areas of cancer treatment and infectious diseases. Its mechanism of action is still being investigated, but its promising pharmacological activities make it an interesting candidate for further research and development.

InChI:InChI=1/C14H13NO2/c1-14(2)8-7-10-12(17-14)9-5-3-4-6-11(9)15-13(10)16/h3-8H,1-2H3,(H,15,16)

Upstream product

• 27428-43-9 5-methoxy-2,2-dimethyl-4a,10b-dihydro-2H-pyrano[3,2-c]quinoline 
• 52851-41-9 2,4-dioxo-1,2,3,4-tetrahydroquinoline 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 6431-84-1 4-hydroxy-3-(3-methylbut-2-enyl) quinolin-2(1H)one 
• 6431-83-0 2,2-dimethyl-2,3,4,10-tetrahydro-pyrano[2,3-b]quinolin-5-one 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 38975-96-1 2,4-dimethoxy-3-(3-methylbut-2-enyl)quinoline 
• 27428-55-3 3-((3,3-dimethyloxiran-2-yl)methyl)-2,4-dimethoxyquinoline 
• 108-10-1 4-methyl-2-pentanone 
• 135299-35-3 ethyl 3-keto-5-methyl-2-hexanoate 
• 135299-39-7 2-isopropyl-4-methylmercapto-3(2H)-oxofuro<3,2-e>quinoline 
• 135299-38-6 4-chloro-3-(3-methyl-2-butenoyl)-2-methylmercapto quinoline 
• 135299-37-5 4-chloro-3-(3-methylbutanoyl)-2-methylmercaptoquinoline 
• 135299-36-4 4-hydroxy-3-(3-methylbutanoyl)-2-methylmercapto quinoline 

Downstream Products

• 6391-66-8 3,4-dihydro-2,2-dimethyl-2H,5H-pyrano<3,2-c>quinolin-5-one 

Relevant articles and documents

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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.

Simple efficient synthesis of pyranoquinoline alkaloids: Flindersine, khaplofoline, haplamine and their analogues

An efficient two step synthesis of pyranoquinoline alkaloids is described. Direct treatment of isoprene with 4-hydroxyquinolin-2(1H)-one in the presence of polyphosphoric acid furnished dihydroflindersine in good yield, and which on dehydrogenation led to a new synthesis of flindersine. Khaplofoline, a linear pyranoquinoline alkaloid, was obtained as a minor product. The syntheses of derivatives are also documented.