112980-33-3

Basic information

• Product Name: 3(2H)-Benzofuranone, 2-[[4-(dimethylamino)phenyl]methylene]-, (Z)-
• CAS NO: 112980-33-3
• Molecular Formula: C17H15NO2
• Molecular Weight: 265.312
• Mol File: 112980-33-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 3(2H)-Benzofuranone, 2-[[4-(dimethylamino)phenyl]methylene]-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3(2H)-Benzofuranone, 2-[[4-(dimethylamino)phenyl]methylene]-, (Z)-(112980-33-3)
• EPA Substance Registry System: 3(2H)-Benzofuranone, 2-[[4-(dimethylamino)phenyl]methylene]-, (Z)-(112980-33-3)

Safety Data

• Hazardous Substances Data: 112980-33-3(Hazardous Substances Data)

Upstream product

• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 65786-13-2 2'-hydroxy-4-dimethylaminochalcone 
• 65786-13-2 (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 118-93-4 o-hydroxyacetophenone 

Relevant articles and documents

Synthesis, crystal structure and two-photon excited fluorescence properties of three aurone derivatives

Three aurone derivatives, Z-2-[(4-N,N-dimethylaminophenyl)methylene] benzofuran-3-one (1), Z-2-[(N-ethylcarbazol-3-yl)methylene]benzofuran-3-one (2) and Z-2-[(pyren-1-yl)methylene]benzofuran-3-one (3) have been synthesized by the cyclization of 2′-hydroxy

THERAPEUTIC AURONES

Substituted aurones were found to have antitrypanosomal, antifungal and immunomodulatory activity. The invention provides novel aurone compounds, pharmaceutical compositions, and methods encompassing medical and veterinary applications.

Probing the aurone scaffold against Plasmodium falciparum: Design, synthesis and antimalarial activity

A library comprising 44 diversely substituted aurones derivatives was synthesized by straightforward aldol condensation reactions of benzofuranones and the appropriately substituted benzaldehydes. Microwave enhanced synthesis using palladium catalyzed protocols was introduced as a powerful strategy for extending the chemical space around the aurone scaffold. Additionally, Mannich-base derivatives, containing a 7-aminomethyl-6-hydroxy substitution pattern at ring A, were also prepared. Screening against the chloroquine resistant Plasmodium falciparum W2 strain identified novel aurones with IC 50 values in the low micromolar range. The most potent compounds contained a basic moiety, with the ability to accumulate in acidic digestive vacuole of the malaria parasite. However, none of those aurones revealed significant activity against hemozoin formation and falcipain-2, two validated targets expressed during the blood stage of P. falciparum infection and functional in digestive vacuole of the parasite. Overall, this study highlight (i) the usefulness of aurones as platforms for synthetic procedures using palladium catalyzed protocols to rapidly deliver lead compounds for further optimization and (ii) the potential of novel aurone derivatives as promising antimalarial compounds.