23158-19-2

Basic information

• Product Name: 2,3,10,11-tetramethoxy-11H-isoquino[3,2-a]isoquinoline
• CAS NO: 23158-19-2
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.3957
• Mol File: 23158-19-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 646.3°C at 760 mmHg
• Flash Point: 196.3°C
• Density: 1.27g/cm³
• Vapor Pressure: 1.37E-16mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 2,3,10,11-tetramethoxy-11H-isoquino[3,2-a]isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,10,11-tetramethoxy-11H-isoquino[3,2-a]isoquinoline(23158-19-2)
• EPA Substance Registry System: 2,3,10,11-tetramethoxy-11H-isoquino[3,2-a]isoquinoline(23158-19-2)

Safety Data

• Hazardous Substances Data: 23158-19-2(Hazardous Substances Data)

Usage

Class

isoquinoline alkaloids

Structure

derived from the isoquinoline structure with four methoxy groups

Biological and pharmacological activities

antiparasitic, anti-inflammatory, and antioxidant properties

Potential

as a drug lead for the treatment of various diseases

Ongoing research

to explore its potential applications in medicine and drug development

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Relevant articles and documents

Coralyne analogs as topoisomerase inhibitors

The present invention provides protoberberine alkaloid derivatives useful as anticancer agents, and methods of use thereof. The invention also provides protoberberine derivatives useful as topoisomerase inhibitors. The invention further provides coralyne and nitidine derivatives which are topoisomerase I-targeted therapeutics effective against camptothecin resistant cancer cells, and are especially effective against CNS tumors.

Protoberberine Alkaloids and Related Compounds as Dual Inhibitors of Mammalian Topoisomerase I and II

Berberine and several structurally-related analogs were evaluated as inhibitors of topoisomerase I and II. The pharmacological activity of protoberberines exhibited a strong dependence upon the type and location of substituents. Several of these alkaloids exhibited activity as inhibitors of topoisomerase II. Among the bicyclic heterocyclic analogs evaluated, none exhibited similar potency to berberrubine as an inhibitor of topoisomerase II. Of the analogs studied, 2,3-desmethylene-9,10-desmethylberberine was the most potent inhibitor of topoisomerase I when assayed in vitro.

Reaction of Protoberberine-type Alkaloids. Part 13. Biogenetic Conversion of Protoberberine Alkaloids into Phthalideisoquinoline Alkaloids

A new convenient and biogenetic-type conversion of the protoberberine alkaloids into the phthalideisoquinoline alkaloids is described.The phthalideisoquinoline 5,6-dimethoxy-3-(6,7-dimethoxyisoquinolin-1-yl)isobenzofuran-1(3H)-one (4) was derived from 8-norcoralyne chloride (1) via 13-oxidonorcoralyne (3) in a one-pot reaction consisting of dye-sensitized photo-oxygenation followed by treatment with sodium borohydride.The conversion of berberine chloride into (+/-)-β-hydrastine (21) was performed by a reaction sequence involving conversion of 8,13a-epidioxy-9,10-dimethoxy- 2,3-methylenedioxy-13-oxo-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine (9) into 1-(2-carboxy-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinoline (11) using pyridinium chloride, followed by methylation and reductive cyclization.