1438408-89-9

Basic information

• Product Name: (E)-3-(4-ethoxybenzylidene)pyrrolidin-2-one
• Synonyms: (E)-3-(4-ethoxybenzylidene)pyrrolidin-2-one
• CAS NO: 1438408-89-9
• Molecular Weight: 217.268
• Mol File: 1438408-89-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (E)-3-(4-ethoxybenzylidene)pyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-(4-ethoxybenzylidene)pyrrolidin-2-one(1438408-89-9)
• EPA Substance Registry System: (E)-3-(4-ethoxybenzylidene)pyrrolidin-2-one(1438408-89-9)

Safety Data

• Hazardous Substances Data: 1438408-89-9(Hazardous Substances Data)

Upstream product

• 10031-82-0 4-ethoxybenzaldehyde 
• 94363-57-2 1-(trifluoroacetyl)-2-pyrrolidinone 
• 616-45-5 2-pyrrolidinon 
• 932-17-2 N-acetylpyrrolidinone 

Downstream Products

• 1438408-91-3 (E)-1-(2-aminoethyl)-3-(4-ethoxybenzylidene)pyrrolidin-2-one trifluoroacetate 
• 1438408-99-1 C₃₄H₃₄N₂O₂ 

Relevant articles and documents

Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare

In our continued efforts to improve the potential utility of the α-methylene-γ-lactone scaffold, 62 new and 59 known natural α-methylenelactam analogues including α-methylene-γ-lactams, α-arylidene-γ and δ-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the α-methylenelactone scaffold. The results of antifungal and cytotoxic activity indicated that among these derivatives compound (E)-1-(2, 6-dichlorobenzyl)-3-(2-fluorobenzylidene) pyrrolidin-2-one (Py51) possessed good selectivity with the highest antifungal activity against Colletotrichum orbiculare with IC50?=?10.4?μM but less cytotoxic activity with IC50?=?141.2?μM (against HepG2 cell line) and 161.2?μM (against human hepatic L02?cell line). Ultrastructural change studies performed by transmission electron microscope showed that Py51 could cause important cell morphological changes in C.?orbiculare, such as plasma membrane detached from cell wall, cell wall thickening, mitochondria disruption, a dramatic increase in vacuolation, and eventually a complete loss in the integrity of organelles. Significantly, mitochondria appeared one of the primary targets, as confirmed by their remarkably aberrant morphological changes. Analysis of structure–activity relationships revealed that incorporation of the aryl group into the α-exo-methylene and the N-benzyl substitution increased the activity. Meanwhile, the α-arylidene-γ-lactams have superiority in selectivity over the 3-arylideneindolin-2-ones. Based on the results, the N-benzyl substituted α-(2-fluorophenyl)-γ-lactam was identified as the most promising natural-based scaffold for further discovering and developing improved crop-protection agents.

Structural modifications of (Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene) thiazolidine-2,4-dione that improve selectivity for inhibiting the proliferation of melanoma cells containing active ERK signaling

We herein report on the pharmacophore determination of the ERK docking domain inhibitor (Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4- dione, which has led to the discovery of compounds with greater selectivities for inhibiting the proliferation of melanoma cells containing active ERK signaling. The Royal Society of Chemistry 2013.