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

Description

Flindersine, a limonoid phytochemical derived from the plant Flindersia acuminata, exhibits a range of biological activities such as cytotoxic, anti-inflammatory, and anti-malarial properties. As a natural product, it holds promise for drug development in cancer treatment and infectious diseases, with its pharmacological activities and mechanisms of action being subjects of ongoing research and development.

Uses

Used in Pharmaceutical Industry:
Flindersine is used as a cytotoxic agent for its potential in cancer treatment, targeting and eliminating cancer cells while causing minimal harm to healthy cells.
Used in Anti-inflammatory Applications:
Flindersine serves as an anti-inflammatory compound, helping to reduce inflammation and associated symptoms in various conditions.
Used in Anti-malarial Treatment:
Flindersine is utilized as an anti-malarial agent, combating malaria-causing parasites and alleviating the disease's effects.
Used in Drug Development:
Flindersine's diverse pharmacological activities make it a valuable candidate for the development of new drugs targeting a range of diseases, including cancer and infectious diseases.

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

• 6431-84-1 4-hydroxy-3-(3-methylbut-2-enyl) quinolin-2(1H)one 
• 91794-23-9 4-keto-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one 
• 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 
• 103-72-0 phenyl isothiocyanate 
• 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 
• 96838-74-3 4-hydroxy-3(1-carboxy-3-methylbut-1-enyl)-2-quinolone 

Downstream Products

• 73776-24-6 2,4-dihydroxy-quinoline-3-carboxylic acid 
• 40059-53-8 ethyl 2,4-dihydroxyquinoline-3-carboxylate 
• 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.