65893-94-9

Basic information

• Product Name: Glabrescione B
• Synonyms: 3-(3',4'-bis(3-methylbut-2-enyloxy)phenyl)-5,7-dimethoxy-4H-chromen-4-one;3-[3,4-Bis-(3-methyl-but-2-enyloxy)-phenyl]-5,7-dimethoxy-chromen-4-one;Glabrescion B
• CAS NO: 65893-94-9
• Molecular Formula: C27H30O6
• Molecular Weight: 450.532
• Mol File: 65893-94-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Glabrescione B(CAS DataBase Reference)
• NIST Chemistry Reference: Glabrescione B(65893-94-9)
• EPA Substance Registry System: Glabrescione B(65893-94-9)

Safety Data

• Hazardous Substances Data: 65893-94-9(Hazardous Substances Data)

Usage

General Description

Glabrescione B is a chemical compound extracted from the plant Euphorbia peplus, often referred to as petty spurge or radium weed. It's known for its anti-cancer properties and is used in oncology as a potential treatment for certain types of cancer, including ovarian cancer. Glabrescione B works by blocking the Hedgehog (Hh) signaling pathway, which is often overactive in various kinds of cancers, and it also inhibits tumor growth by disrupting tumor cell proliferation and survival.

Synthetic route

3-(3',4'-dihydroxyphenyl)-5,7-dimethoxy-4H-chromen-4-one + prenyl bromide (870-63-3) → 3-(3',4'-bis(3-methylbut-2-enyloxy)phenyl)-5,7-dimethoxy-4H-chromen-4-one (65893-94-9)

Conditions	Yield
Stage #1: 3-(3',4'-dihydroxyphenyl)-5,7-dimethoxy-4H-chromen-4-one With potassium carbonate In acetone at 20℃; for 0.166667h; Stage #2: prenyl bromide In acetone at 80℃;	86%

1-(2,4,6-trimethoxyphenyl)ethanone (832-58-6) → 3-(3',4'-bis(3-methylbut-2-enyloxy)phenyl)-5,7-dimethoxy-4H-chromen-4-one (65893-94-9)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: boron tribromide / dichloromethane / 2 h / 20 °C / Inert atmosphere 2.1: 3 h / 95 °C 3.1: iodine / methanol / 1 h / 20 °C 4.1: sodium carbonate / 1,2-dimethoxyethane; water / 2 h / 45 °C 5.1: lead(IV) tetraacetate / benzene / 80 °C / Inert atmosphere 5.2: 6 h / 25 °C 6.1: potassium carbonate / acetone / 0.17 h / 20 °C 6.2: 80 °C View Scheme

2-hydroxy-4,6-dimethoxyacetophenone (90-24-4) → 3-(3',4'-bis(3-methylbut-2-enyloxy)phenyl)-5,7-dimethoxy-4H-chromen-4-one (65893-94-9)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 3 h / 95 °C 2.1: iodine / methanol / 1 h / 20 °C 3.1: sodium carbonate / 1,2-dimethoxyethane; water / 2 h / 45 °C 4.1: lead(IV) tetraacetate / benzene / 80 °C / Inert atmosphere 4.2: 6 h / 25 °C 5.1: potassium carbonate / acetone / 0.17 h / 20 °C 5.2: 80 °C View Scheme

3-dimethylamino-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one (187877-87-8) → 3-(3',4'-bis(3-methylbut-2-enyloxy)phenyl)-5,7-dimethoxy-4H-chromen-4-one (65893-94-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: iodine / methanol / 1 h / 20 °C 2.1: sodium carbonate / 1,2-dimethoxyethane; water / 2 h / 45 °C 3.1: lead(IV) tetraacetate / benzene / 80 °C / Inert atmosphere 3.2: 6 h / 25 °C 4.1: potassium carbonate / acetone / 0.17 h / 20 °C 4.2: 80 °C View Scheme

5,7-dimethoxy-3-iodo-4H-1-benzopyran-4-one → 3-(3',4'-bis(3-methylbut-2-enyloxy)phenyl)-5,7-dimethoxy-4H-chromen-4-one (65893-94-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium carbonate / 1,2-dimethoxyethane; water / 2 h / 45 °C 2.1: lead(IV) tetraacetate / benzene / 80 °C / Inert atmosphere 2.2: 6 h / 25 °C 3.1: potassium carbonate / acetone / 0.17 h / 20 °C 3.2: 80 °C View Scheme

3-(3',4'-methylendioxyphenyl)-5,7-dimethoxy-4H-chromen-4-one (22044-59-3) → 3-(3',4'-bis(3-methylbut-2-enyloxy)phenyl)-5,7-dimethoxy-4H-chromen-4-one (65893-94-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lead(IV) tetraacetate / benzene / 80 °C / Inert atmosphere 1.2: 6 h / 25 °C 2.1: potassium carbonate / acetone / 0.17 h / 20 °C 2.2: 80 °C View Scheme

Upstream product

• 22044-59-3 3-(3',4'-methylendioxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 
• 187877-87-8 3-dimethylamino-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 870-63-3 prenyl bromide 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 

Relevant articles and documents

MULTITARGET HEDGEHOG PATHWAY INHIBITORS AND USES THEREOF

The present invention concerns compounds that selectively inhibit the activity of the Hedgehog (Hh) pathway, their preparation and uses thereof. The compounds of the present invention are useful in treating Hh-dependent tumors, such as medulloblastoma (MB).