75116-77-7

Basic information

• Product Name: diethyl 2-(3-benzoylphenyl)malonate
• Synonyms: diethyl 2-(3-benzoylphenyl)malonate
• CAS NO: 75116-77-7
• Molecular Weight: 340.376
• Mol File: 75116-77-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: diethyl 2-(3-benzoylphenyl)malonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl 2-(3-benzoylphenyl)malonate(75116-77-7)
• EPA Substance Registry System: diethyl 2-(3-benzoylphenyl)malonate(75116-77-7)

Safety Data

• Hazardous Substances Data: 75116-77-7(Hazardous Substances Data)

Upstream product

• 585-76-2 m-bromobenzoic acid 
• 1711-09-7 3-bromobenzoyl chloride 
• 1016-77-9 3-bromobenzophenone 
• 105-53-3 diethyl malonate 
• 75116-76-6 diethyl (3-benzoylphenyl)oxalacetate 

Downstream Products

• 159490-55-8 2-(3-benzoylphenyl)propanoic-3,3,3-d₃ acid 
• 60658-04-0 ethyl 2-<3-benzoylphenyl>propionate 
• 22071-15-4 ketoprofen 

Relevant articles and documents

The Effects of Prodrug Size and a Carbonyl Linker on l-Type Amino Acid Transporter 1-Targeted Cellular and Brain Uptake

The l-type amino acid transporter 1 (LAT1, SLC7A5) imports dietary amino acids and amino acid drugs (e. g., l-DOPA) into the brain, and plays a role in cancer metabolism. Though there have been numerous reports of LAT1-targeted amino acid-drug conjugates (prodrugs), identifying the structural determinants to enhance substrate activity has been challenging. In this work, we investigated the position and orientation of a carbonyl group in linking hydrophobic moieties including the anti-inflammatory drug ketoprofen to l-tyrosine and l-phenylalanine. We found that esters of meta-carboxyl l-phenylalanine had better LAT1 transport rates than the corresponding acylated l-tyrosine analogues. However, as the size of the hydrophobic moiety increased, we observed a decrease in LAT1 transport rate with a concomitant increase in potency of inhibition. Our results have important implications for designing amino acid prodrugs that target LAT1 at the blood-brain barrier or on cancer cells.

ENANTIOSELECTIVE SYNTHESIS AND ABSOLUTE CONFIGURATION OF (+)-α-(3-BENZOYLPHENYL)PROPIONIC ACID

Asymmetric homogeneous hydrogenation of α-(3-benzoylphenyl)acrylic acid (4), which is preparared in 90percent overall yield from (3-benzoylphenyl)acetic acid (1), affords (+)-α-(3-benzoylphenyl)propionic acid, (+)-5, in 93.7percent chemical and 67.4percent optical yield.The absolute configuration of (+)-5 is correlated with that of (+)-(S)-hydratropic acid via (+)-α-(3-benzylphenyl)propionic acid, (+)-6.The origin of the CD bands of (+)-6 is discussed and comparison of chiroptical data with those of (+)-(S)-hydratropic acid, reveals that (+)-6 has an S configuration.Since (+)-6 is chemically correlated with (+)-5, the absolute S configuration of this enantiomer is confirmed.