1415976-00-9

Basic information

• Product Name: (E)-3-(benzofuran-2-yl)-2-cyano-N-(4-methoxybenzyl)acrylamide
• Synonyms: (E)-3-(benzofuran-2-yl)-2-cyano-N-(4-methoxybenzyl)acrylamide
• CAS NO: 1415976-00-9
• Molecular Weight: 332.359
• Mol File: 1415976-00-9.mol

Chemical Properties

• CAS DataBase Reference: (E)-3-(benzofuran-2-yl)-2-cyano-N-(4-methoxybenzyl)acrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-(benzofuran-2-yl)-2-cyano-N-(4-methoxybenzyl)acrylamide(1415976-00-9)
• EPA Substance Registry System: (E)-3-(benzofuran-2-yl)-2-cyano-N-(4-methoxybenzyl)acrylamide(1415976-00-9)

Safety Data

• Hazardous Substances Data: 1415976-00-9(Hazardous Substances Data)

Upstream product

• 2393-23-9 4-methoxy-benzylamine 
• 288154-72-3 2-cyano-N-(4-methoxybenzyl)acetamide 
• 4265-16-1 2-formylbenzo[b]furan 

Relevant articles and documents

Synthesis and Cytotoxicity of Octahydroepoxyisoindole-7-carboxylic Acids and Norcantharidin–Amide Hybrids as Norcantharidin Analogues

Octahydroepoxyisoindole analogues of norcantharidin were accessed through a Diels–Alder reaction of an amine-substituted furan with maleic anhydride and subsequent reduction of the bicyclo[2.2.1]heptene olefin. Despite retention of the carboxylate and the ether bridgehead known to impart cytotoxic activity to norcantharidin, none of these analogues displayed notable cytotoxicity against the 11 cell lines examined: HT29 (colon), MCF-7 (breast), A2780 (ovarian), H460 (lung), A431 (skin), Du145 (prostate), BE2-C (neuroblastoma), SJ-G2 and U87 (glioblastoma), MIA (pancreatic), and SMA (spontaneous murine astrocytoma). The incorporation of an amino-substituted system post-synthesis of norcantharidin afforded facile access to 14 acid/amide-substituted norcantharidin analogues. Of these, only four displayed sufficient activity at the initial 25 μm compound screening dose to warrant full evaluation of growth inhibition. Common to these analogues was the presence of a 4-biphenyl moiety, and in particular 3-(2-(furan-2-ylmethyl)-3-(4-biphenylamino)-3-oxopropylcarbamoyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid (13 c) and 3-(2-(pyrrole-2-ylmethyl)-3-(4-biphenylamino)-3-oxopropylcarbamoyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid (24) displayed high levels of cytotoxicity, returning GI50 values of 15 nm (HT29) to 2.9 μm (U87) and 17 nm (SMA) to 2.8 μm (U87), respectively. These are the most cytotoxic norcantharidin analogues reported to date.

Focused library development of 2-phenylacrylamides as broad spectrum cytotoxic agents

With our lead compound (E)-3-(4-chlorophenyl)-2-(1H-pyrrole-2-carbonyl) acrylonitrile (1) inducing 50% growth inhibition of 11 cancer cell lines at 27-61 μM, potency enhancements were rapidly established through the synthesis of a series of focused compou