65893-94-9

Usage

Uses

Used in Oncology:
Glabrescione B is used as an anti-cancer agent for its ability to block the overactive Hedgehog (Hh) signaling pathway, which is often implicated in the development of various cancers. This action helps in controlling tumor growth and potentially treating cancer.
Used in Cancer Treatment:
Glabrescione B is used as a therapeutic agent in the treatment of certain types of cancer, including ovarian cancer. Its mechanism of action involves disrupting tumor cell proliferation and survival, making it a promising candidate for cancer therapy.
Used in Drug Development:
Glabrescione B is used as a lead compound in the development of new drugs targeting the Hedgehog (Hh) signaling pathway. Its potential to inhibit this pathway and affect tumor growth makes it a valuable asset in the search for novel cancer treatments.

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 academic research and scientific papers

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).