905970-80-1

Basic information

• Product Name: 4-((but-3-enyl)phenethylcarbamoyl)pent-4-enoic acid methyl ester
• Synonyms: 4-((but-3-enyl)phenethylcarbamoyl)pent-4-enoic acid methyl ester
• CAS NO: 905970-80-1
• Molecular Weight: 315.412
• Mol File: 905970-80-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-((but-3-enyl)phenethylcarbamoyl)pent-4-enoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((but-3-enyl)phenethylcarbamoyl)pent-4-enoic acid methyl ester(905970-80-1)
• EPA Substance Registry System: 4-((but-3-enyl)phenethylcarbamoyl)pent-4-enoic acid methyl ester(905970-80-1)

Safety Data

• Hazardous Substances Data: 905970-80-1(Hazardous Substances Data)

Upstream product

• 5621-44-3 dimethyl 2-methylenepentanedioate 
• 3621-79-2 2-methyleneglutaric acid 
• 93633-32-0 5-methoxy-2-methylene-5-oxopentanoic acid 
• 867324-06-9 N-phenethylbut-3-en-1-amine 
• 64-04-0 phenethylamine 

Downstream Products

• 905970-84-5 3-(2-oxo-1-phenethyl-1,2,5,6-tetrahydropyridin-3-yl)propionic acid methyl ester 

Relevant articles and documents

Lactam-based HDAC inhibitors for anticancer chemotherapy: Restoration of RUNX3 by posttranslational modification and epigenetic control

Expression and stability of the tumor suppressor runt-related transcription factora 3 (RUNX3) are regulated by histone deacetylase (HDAC). HDAC inhibition alters epigenetic and posttranslational stability of RUNX3, leading to tumor suppression. However, HDAC inhibitors can nonselectively alter global gene expression through chromatin remodeling. Thus, lactam-based HDAC inhibitors were screened to identify potent protein stabilizers that maintain RUNX3 stability by acetylation. RUNX activity and HDAC inhibition were determined for 111 lactam-based analogues through a cell-based RUNX activation and HDAC inhibition assay. 3-[1-(4-Bromobenzyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-N- hydroxypropanamide (11-8) significantly increased RUNX3 acetylation and stability with relatively low RUNX3 mRNA expression and HDAC inhibitory activity. This compound showed significant antitumor effects, which were stronger than SAHA, in an MKN28 xenograft model. Thus, we propose a novel strategy, in which HDAC inhibitors serve as antitumor chemotherapeutic agents that selectively target epigenetic regulation and protein stability of RUNX3.

Synthesis, enzymatic inhibition, and cancer cell growth inhibition of novel δ-lactam-based histone deacetylase (HDAC) inhibitors

δ-Lactam-based hydroxamic acids, inhibitors of histone deacetylase (HDAC), have been synthesized via ring closure metathesis of key diene intermediates followed by conversion to hydroxamic acid analogues. The hydroxamic acids 12a, 12b, and 17c showed potent inhibitory activity in HDAC enzyme assay. The hydroxamic acid 12b exhibited growth inhibitory activity on five human tumor cell lines, showing good sensitivity on the MDA-MB-231 breast tumor cell.