854847-61-3

Basic information

• Product Name: 4-Ethyl-5-methyl-5,6-dihydro-[1,3]dioxolo[4,5-j]phenanthridine
• Synonyms: 4-Ethyl-5,6-Dihydro-5-methyl-[1,3]dioxolo[4,5-j]phenanthridine;4-Ethyl-5-methyl-5,6-dihydro-[1,3]dioxolo[4,5-j]phenanthridine;HLY78
• CAS NO: 854847-61-3
• Molecular Formula: C17H17NO2
• Molecular Weight: 267.32238
• Mol File: 854847-61-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 444.0±34.0 °C(Predicted)
• Appearance: white to beige/
• Density: 1.208±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble5mg/mL, clear (warmed)
• PKA: 4?+-.0.20(Predicted)
• CAS DataBase Reference: 4-Ethyl-5-methyl-5,6-dihydro-[1,3]dioxolo[4,5-j]phenanthridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ethyl-5-methyl-5,6-dihydro-[1,3]dioxolo[4,5-j]phenanthridine(854847-61-3)
• EPA Substance Registry System: 4-Ethyl-5-methyl-5,6-dihydro-[1,3]dioxolo[4,5-j]phenanthridine(854847-61-3)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 854847-61-3(Hazardous Substances Data)

Usage

Biological Activity

hly78 is a positive modulator of the wnt/β-catenin pathway.the evolutionarily conserved wnt/β-catenin signaling pathway has important roles in embryonic development and human diseases. during embryogenesis, the wnt signaling pathway regulates cell fate specification, differentiation, proliferation and survival. inappropriate regulation of the wnt signaling pathway is usually related to the progression of various human diseases including cancer, familial exudative vitreoretinopathy, alzheimer’s disease, and bone formation disorders.

in vitro

by screening a synthetic chemical library of lycorine derivatives, hly78 was identified as an activator of the wnt/β-catenin signaling pathway, which acted in a wnt ligand-dependent manner. hly78 was found to be alble to target the dix domain of axin and potentiate the axin-lrp6 association, therefore leading to the promotion of lrp6 phosphorylation and wnt signaling transduction. in addition, this study also identified the critical residues on axin for hly78 binding and suggested that hly78 might weaken the autoinhibition of axin1 [1].

in vivo

in-vivo study showed that hly78 could synergistically act with wnt in the embryonic development of zebrafish and increase the expression of the conserved hematopoietic stem cell (hsc) markers, cmyb and runx1, in zebrafish embryos [1].

references

[1] wang, s. ,yin, j.,chen, d., et al. small-molecule modulation of wnt signaling via modulating the axin-lrp5/6 interaction. nature chemical biology 9, 579-585 (2013).

Upstream product

• 23778-35-0 5-methyl-4-vinyl-5,6-dihydro-[1,3]dioxolo[4,5-j]phenanthridine 
• 872296-11-2 4-ethyl-5-methyl-5H-[1,3]dioxolo[4,5-j]phenanthridin-6-one 
• 476-28-8 lycorine 
• 2492-05-9 1,2-diacetoxylycorine 
• 2188-68-3 (1S,2S,12bS,12cS)-1,2-diol-2,4,5,7,12b,12c-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine hydrochloride 
• 15069-99-5 (1α,2β)-3,12-didehydro-1,2-dihydroxy-6-methyl-9,10-[methylenebis(oxy)]galanthanium iodide 

Relevant articles and documents

Synthesis and antiplasmodial activity of lycorine derivatives

Twenty seven lycorine derivatives were prepared and evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum. The best antiplasmodial activities were achieved with lycorine derivatives that present free hydroxyl groups at C-1 and C-2 or esterified as acetates or isobutyrates. The double bond C-2-C-3 is also important for the activity. Concerning to the antiplasmodial activity of the secolycorines, the higher values were obtained with the replacement of the methylenedioxy moiety by hydroxyl or acetate groups and with methyl substituent attached to the nitrogen atom.

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Phenanthridine Derivatives, Preparation Methods and Uses Thereof

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