65367-81-9

Basic information

• Product Name: 5-methyl-5,10a-dihydro[1,3]dioxolo[4,5-j]phenanthridine
• CAS NO: 65367-81-9
• Molecular Formula: C₁₅H₁₃NO₂
• Molecular Weight: 239.2692
• Mol File: 65367-81-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 459.7°C at 760 mmHg
• Flash Point: 203.1°C
• Density: 1.32g/cm³
• Vapor Pressure: 1.24E-08mmHg at 25°C
• Refractive Index: 1.687
• CAS DataBase Reference: 5-methyl-5,10a-dihydro[1,3]dioxolo[4,5-j]phenanthridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-5,10a-dihydro[1,3]dioxolo[4,5-j]phenanthridine(65367-81-9)
• EPA Substance Registry System: 5-methyl-5,10a-dihydro[1,3]dioxolo[4,5-j]phenanthridine(65367-81-9)

Safety Data

• Hazardous Substances Data: 65367-81-9(Hazardous Substances Data)

Upstream product

• 40141-79-5 2-bromo-N-methyl-4,5-methylenedioxybenzanilide 
• 224-11-3 trisphaeridine 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 120-57-0 piperonal 
• 40141-86-4 [1,3]dioxolo[4,5-j]-6(5H)-phenanthridinone 
• 74-88-4 methyl iodide 
• 6120-26-9 6-bromobenzo[d][1,3]dioxole-5-carbonitrile 
• 40141-98-8 N-methylcrinasiadine 
• 108-94-1 cyclohexanone 
• 507-79-9 tazettine 

Downstream Products

• 40141-98-8 N-methylcrinasiadine 

Relevant articles and documents

Metal-free tandem carbene N-H insertions and C-C bond cleavages

A metal-free C-H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C-C cleavage. Compared to the simple N-H insertion manipulation of diazo, this method elegantly accomplishes a tandem N-H insertion/SEAr/C-C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and bicolorine alkaloids. This journal is

Synthesis of phenanthridine skeletal Amaryllidaceae alkaloids

Strategies for the synthesis of Amaryllidaceae alkaloids, including crinasiadine, trisphaeridine, bicolorine, N-methylcrinasiadine, 5,6-dihydrobicolorine, galanthindole, lycosinine A and lycosinine B were reported. Investigation of optionally synthetic routes to approach bicolorine, 5,6-dihydrobicolorine, trisphaeridine and N-methylcrinasiadine were demonstrated as well. In addition, three structurally related alkaloids galanthindole, lycosinine A and lycosinine B were concisely prepared by using Suzuki coupling reaction as the key step.

Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs

The plant alkaloid lycobetaine has potent topoisomerase-targeting properties and shows anticancer activity. Based on these findings, several lycobetaine analogs were synthesized mainly differing in their substituents at 2, 8 and 9 position and their biological activities were evaluated. The topoisomerase-targeting properties and cytotoxicity of these structural analogs were assessed in the human gastric carcinoma cell line GXF251L. Performing a plasmid relaxation assay, an increased inhibition of topoisomerase I was found with N-methylphenanthridinium chlorides bearing a 8,9-methylenedioxy moiety or a methoxy group in 2-position. Furthermore, quaternized phenanthridinium derivatives bearing either a 2-methoxy or a 8,9-methylenedioxy moiety in conjunction with a 2-hydroxy or 2-methoxy group display potent topoisomerase II inhibition as shown by decatenation of kinetoplast DNA. In general, the N-methylphenanthridinium chlorides possess more potency in inhibiting topoisomerase I than topoisomerase II. All quaternized derivatives also exhibited potent inhibition of tumor cell growth in the low micromolar concentration range. Hence, N-methylphenanthridinium compounds were found to represent a promising class of compounds, potently inhibiting both, topoisomerases I and II, and may be further developed into clinically useful topoisomerase inhibitors.