1390630-46-2

Basic information

• Product Name: (E)-ethyl 3-(3-bromo-4-hydroxyphenyl)-2-{[(tetrahydro-2H-pyran-2-yl)oxy]imino}propanoate
• Synonyms: (E)-ethyl 3-(3-bromo-4-hydroxyphenyl)-2-{[(tetrahydro-2H-pyran-2-yl)oxy]imino}propanoate
• CAS NO: 1390630-46-2
• Molecular Weight: 386.243
• Mol File: 1390630-46-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (E)-ethyl 3-(3-bromo-4-hydroxyphenyl)-2-{[(tetrahydro-2H-pyran-2-yl)oxy]imino}propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-ethyl 3-(3-bromo-4-hydroxyphenyl)-2-{[(tetrahydro-2H-pyran-2-yl)oxy]imino}propanoate(1390630-46-2)
• EPA Substance Registry System: (E)-ethyl 3-(3-bromo-4-hydroxyphenyl)-2-{[(tetrahydro-2H-pyran-2-yl)oxy]imino}propanoate(1390630-46-2)

Safety Data

• Hazardous Substances Data: 1390630-46-2(Hazardous Substances Data)

Upstream product

• 2973-78-6 3-bromo-4-hydroxybenzylaldehyde 
• 58714-57-1 E-2-(4-Hydroxybenzyliden)acetessigsaeure-ethylester 
• 1390630-45-1 C₁₃H₁₅BrO₄ 
• 110-87-2 3,4-dihydro-2H-pyran 
• 172854-02-3 (E)-ethyl 3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanoate 

Downstream Products

• 109152-30-9 psammaplin A 

Relevant articles and documents

Synthesis and biological activity of selenopsammaplin A and its analogues as antitumor agents with DOT1L inhibitory activity

Disruptor of telomeric silencing-1 like (DOT1L) is a histone H3 methyltransferase which specifically catalyzes the methylation of histone H3 lysine-79 residue. Recent findings demonstrate that DOT1L is abnormally overexpressed and the upregulated DOT1L evokes the proliferation and metastasis in human breast cancer cells. Therefore, the DOT1L inhibitor is considered a promising strategy to treat breast cancers. Non-nucleoside DOT1L inhibitors, selenopsammaplin A and its analogues, were firstly reported in the present study. Selenopsammaplin A was newly designed and synthesized with 25% overall yield in 8 steps from 3-bromo-4-hydroxybenzaldahyde, and thirteen analogues of selenopsammaplin A were prepared for structure–activity relationship studies of their cytotoxicity against cancer cells and inhibitory activity toward DOT1L for antitumor potential. All synthetic selenopsammaplin A analogues exhibited the higher cytotoxicity compared to psammaplin A with up to 6 – 60 times depending on cancer cells, and most analogues showed significant inhibitory activities against DOT1L. Among the prepared analogues, the phenyl analogue (10) possessed the most potent activity with both cytotoxicity and inhibition of DOT1L. Compound 10 also exhibited the antitumor and antimetastatic activity in an orthotopic mouse metastasis model implanted with MDA-MB-231 human breast cancer cells. These biological findings suggest that analogue 10 is a promising candidate for development as a cancer chemotherapeutic agent in breast cancers.

Efficient synthetic method of Psammaplin A

A new concise and efficient synthetic method of Psammaplin A was developed. Psammaplin A was obtained with 50% overall yield in nine steps from p-hydroxybenzaldehyde and ethyl acetoacetate via Knoevenagel condensation and direct nitrosation as key steps.