89709-71-7

Basic information

• Product Name: Benzenepropanoic acid, 4-(phenylmethyl)-
• CAS NO: 89709-71-7
• Molecular Formula: C16H16O2
• Molecular Weight: 240.302
• Mol File: 89709-71-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzenepropanoic acid, 4-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid, 4-(phenylmethyl)-(89709-71-7)
• EPA Substance Registry System: Benzenepropanoic acid, 4-(phenylmethyl)-(89709-71-7)

Safety Data

• Hazardous Substances Data: 89709-71-7(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 54411-77-7 methyl p-benzoyl-2,3-dihydrocinnamate 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 285992-38-3 ethyl (E)-3-(4-benzylphenyl)acrylate 
• 2116-36-1 1-benzyl-4-bromo-benzene 
• 90-90-4 (4-bromophenyl)(phenyl)methanone 
• 18908-76-4 ethyl 3-(4-benzylphenyl)propanoate 
• 71388-83-5 p-benzoyl-2,3-dihydrocinnamic acid 
• 96187-79-0 1-(4-benzylphenyl)propan-1-one 

Downstream Products

• 1356067-56-5 (+/-)-tetrahydro-2H-pyran-2-ylmethyl 3-(4-benzylphenyl)propanoate 
• 1356067-52-1 (+/-)-oxiran-2-ylmethyl 3-(4-benzylphenyl)propanoate 

Relevant articles and documents

Structure-activity relationship of a new series of reversible dual monoacylglycerol lipase/fatty acid amide hydrolase inhibitors

The two endocannabinoids, anandamide (AEA) and 2-arachidonoylglycerol (2-AG), play independent and nonredundant roles in the body. This makes the development of both selective and dual inhibitors of their inactivation an important priority. In this work we report a new series of inhibitors of monoacylglycerol lipase (MAGL) and fatty acid amide hydrolase (FAAH). Among them, (±)-oxiran-2-ylmethyl 6-(1,1′-biphenyl-4-yl)hexanoate (8) and (2R)-(-)-oxiran-2-ylmethyl(4-benzylphenyl)acetate (30) stand out as potent inhibitors of human recombinant MAGL (IC50 (8) = 4.1 μM; IC 50 (30) = 2.4 μM), rat brain monoacylglycerol hydrolysis (IC 50 (8) = 1.8 μM; IC50 (30) = 0.68 μM), and rat brain FAAH (IC50 (8) = 5.1 μM; IC50 (30) = 0.29 μM). Importantly, and in contrast to the other previously described MAGL inhibitors, these compounds behave as reversible inhibitors either of competitive (8) or noncompetitive nature (30). Hence, they could be useful to explore the therapeutic potential of reversible MAGL inhibitors.

Structure-activity relationships of α-ketooxazole inhibitors of fatty acid amide hydrolase

A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1-napthyl, K, - 2.6 nM), with 5hh (aryl -3-ClPh, Ki = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, Ki = 3 nM, or 13d, 2-position OH, Ki = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of >100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.