60142-17-8

Basic information

• Product Name: dioncophylline A
• Synonyms: dioncophylline A;(1R)-7-[(aS)-2-Methyl-4,5-dimethoxy-1-naphthalenyl]-1β,3α-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol;(1R)-7-[(aS)-4,5-Dimethoxy-2-methyl-1-naphtyl]-1,2,3,4-tetrahydro-1β,3α-dimethylisoquinolin-8-ol
• CAS NO: 60142-17-8
• Molecular Formula: C24H27NO3
• Molecular Weight: 377.47608
• Mol File: 60142-17-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 478.8°Cat760mmHg
• Flash Point: 243.4°C
• Appearance: /
• Density: 1.128g/cm³
• Vapor Pressure: 8.59E-10mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: dioncophylline A(CAS DataBase Reference)
• NIST Chemistry Reference: dioncophylline A(60142-17-8)
• EPA Substance Registry System: dioncophylline A(60142-17-8)

Safety Data

• Hazardous Substances Data: 60142-17-8(Hazardous Substances Data)

Usage

Description

Dioncophylline A is an isoquinoline alkaloid, specifically a naphthylisoquinoline alkaloid, which is derived from the roots and stem barks of Triphyophyllum peltatum. It is characterized by its unique biaryl structure, resulting from the substitution of the hydrogen at the 7-position of (1R,3R)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol by a 4,5-dimethoxy-2-methylnaphthalen-1-yl group. Dioncophylline A exhibits a range of biological activities, including antifungal, antimalarial, antineoplastic, and molluscicidal properties.

Uses

Used in Pharmaceutical Industry:
Dioncophylline A is used as an active pharmaceutical ingredient for its diverse therapeutic applications. Its antineoplastic activity makes it a potential candidate for the development of anticancer drugs, targeting various types of cancer. Additionally, its antimalarial properties suggest its potential use in the treatment of malaria, a disease caused by Plasmodium parasites.
Used in Antifungal Applications:
In the field of antifungal agents, dioncophylline A is used as a potent antifungal compound to combat various fungal infections. Its ability to inhibit fungal growth and proliferation makes it a valuable asset in the development of new antifungal drugs, particularly for resistant strains.
Used in Molluscicidal Applications:
Dioncophylline A is used as a molluscicide, specifically for the control of snail and slug populations that can cause significant damage to agricultural crops and spread diseases. Its molluscicidal activity makes it a potential tool in integrated pest management strategies to protect crops and reduce the reliance on chemical pesticides.
Used in Antimalarial Applications:
In the context of antimalarial drugs, dioncophylline A is used as a potential therapeutic agent to treat malaria, a life-threatening disease caused by Plasmodium parasites. Its antimalarial properties offer the possibility of developing new drugs to combat drug-resistant strains of the parasite and improve the treatment outcomes for patients suffering from malaria.

InChI:InChI=1/C24H27NO3/c1-13-11-20(28-5)23-17(7-6-8-19(23)27-4)21(13)18-10-9-16-12-14(2)25-15(3)22(16)24(18)26/h6-11,14-15,25-26H,12H2,1-5H3/t14-,15-/m1/s1

Upstream product

• 129437-12-3 (1S,3S)-2-Benzyl-7-(2-hydroxymethyl-4,5-dimethoxy-naphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-8-ol 
• 129437-12-3 (1R,3R,7M)-2-benzyl-1,2,3,4-tetrahydro-7-(2-hydroxymethyl-4,5-dimethoxynaphth-1-yl)-1,3-dimethylisoquinolin-8-ol 
• 129437-10-1 1-Bromo-4,5-dimethoxy-naphthalene-2-carboxylic acid (1S,3S)-2-benzyl-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-8-yl ester 
• 129437-11-2 (2S,4S)-3-Benzyl-8,9-dimethoxy-2,4-dimethyl-1,2,3,4-tetrahydro-5-oxa-3-aza-benzo[c]chrysen-6-one 
• 104292-11-7 1-Bromo-4,5-dimethoxy-naphthalene-2-carbonyl chloride 
• 129437-10-1 1-Bromo-4,5-dimethoxy-naphthalene-2-carboxylic acid (1R,3R)-2-benzyl-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-8-yl ester 
• 139343-51-4 (2R,4R)-3-benzyl-1,3,4,6-tetrahydro-8,9-dimethoxy-2,4-dimethyl-6-oxo-2H-naphtho<1',2':4,5>pyrano<3,2-h>isoquinoline 
• 104292-12-8 (1R,3R)-2-Benzyl-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-6-ol 
• 129519-18-2 (1R,3R)-2-Benzyl-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-8-ol 

Related news

On the structure of the dioncophyllaceae alkaloids dioncophylline A (cas 60142-17-8) (“triphyophylline”) and “O-Methyl-Triphyophylline”07/17/2019

The naphthyl isoquinoline alkaloid “triphyophylline” is structurally re-investigated. The constitution, as well as the relative configurations at C-1 and C-3, are confirmed as published previously. “Triphyophylline” is found to be a stable rotational isomer with respect to the biaryl linkage...detailed

Feeding deterrency and growth retarding activity of the naphthylisoquinoline alkaloid dioncophylline A (cas 60142-17-8) against Spodoptera littoralis07/15/2019

The naphthylisoquinoline alkaloid dioncophylline A was studied for antifeedant activity against larvae of the polyphagous herbivore Spodoptera littoralis. When neonate larvae were reared on artificial diet spiked with concentrations of dioncophylline A as present in plant material of Triphyophyl...detailed

The absolute stereostructure of dioncophylline A (cas 60142-17-8) by anomalous X-ray dispersion of a 5-bromo derivative07/13/2019

The absolute configuration of the naphthylisoquinoline alkaloid dioncophylline A was determined by anomalous X-ray dispersion crystal structure analysis of its bisbenzylated bromo derivative. © 1997 Elsevier Science Ltd. All rights reserveddetailed

Larvicidal activity of the naphthylisoquinoline alkaloid dioncophylline A (cas 60142-17-8) against the malaria vector Anopheles stephensi07/12/2019

The larvicidal activity of dioncophylline A, a naphthylisoquinoline alkaloid derived from the tropical vine Triphyophyllum peltatum (Dioncophyllaceae), was investigated against the malaria vector Anopheles stephensi. In direct and indirect inhibition assays it was demonstrated that the younger l...detailed

Quantum chemical CD calculations of dioncophylline A (cas 60142-17-8) in the solid state07/11/2019

Although dioncophylline A (1) is the certainly best-investigated naphthylisoquinoline alkaloid, it still represents a challenging case for theoretical stereochemical investigations. Its biaryl axis, although being configurationally stable, still has a certain degree of rotational flexibility, ra...detailed

Relevant articles and documents

First Total Synthesis of (-)-Dioncophylline A ("Triphyophylline") and of the Selected Stereoisomers: Complete (Revised) Stereostrucure

The first total synthesis of dioncophylline A (previously "triphyophylline") and some selected stereoisomers is described, using an intramolecular-type mixed aryl coupling method via ester-type prefixed molecular moieties.Simultaneously, this synthesis establishes the complete (revised) stereostructure of dioncophylline A as 1a, which is thereby the first fully elucidated naphthylisoquinoline alkaloid of Dioncophyllaceae.