51994-35-5

Usage

Class

Phenylketones

Structure

Biphenyl group attached to a five-carbon oxovaleric acid chain

Uses

Building block in the synthesis of pharmaceuticals related to neurological disorders and psychiatric conditions, reagent in organic synthesis and medicinal chemistry research

Characteristics

Unique structure and functional groups, valuable tool for the development of new drugs and therapeutic agents

InChI:InChI=1/C17H16O3/c18-16(7-4-8-17(19)20)15-11-9-14(10-12-15)13-5-2-1-3-6-13/h1-3,5-6,9-12H,4,7-8H2,(H,19,20)

Upstream product

• 108-55-4 glutaric anhydride, 
• 92-52-4 biphenyl 

Downstream Products

• 51994-31-1 5-(1,1'-biphenyl-4-yl)pentanoic acid 

Relevant academic research and scientific papers

Visible Light-Driven, Copper-Catalyzed Aerobic Oxidative Cleavage of Cycloalkanones

A visible light-driven, copper-catalyzed aerobic oxidative cleavage of cycloalkanones has been presented. A variety of cycloalkanones with varying ring sizes and various α-substituents reacted well to give the distal keto acids or dicarboxylic acids with moderate to good yields.

Visible-Light-Promoted Metal-Free Aerobic Oxidation of Primary Amines to Acids and Lactones

A unique metal-free aerobic oxidation of primary amines via visible light photocatalytic double carbon–carbon bonds cleavage and multi carbon–hydrogen bonds oxidation was observed. Aerobic oxidation of primary amines could be controlled to afford acids by using dioxane with 18 W CFL, and lactones by using DMF with 8 W green LEDs, respectively. A plausible mechanism was proposed based on control experiments. This observation showed direct evidences for the fragmentation in the aerobic oxidation of aliphatic primary amines.

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.

ON THE QUANTITATIVE RELATIONS BETWEEN STRUCTURE AND ANTIAGGREGATION ACTIVITY OF ω-ARYL-ω-OXOALKANOIC ACIDS

A series of ω-aryl-ω-oxoalkanoic acids, I-IV, has been prepared and investigated for dissociation constants in 80percent methylcellosolve, retention characteristics in thin-layer partition chromatography and partition coefficients P in the system octanol-water.Also evaluated were their anti-inflammatory efficacy and inhibitory effect on the platelet aggregation induced by collagen.Analysing the relations between structure and antiaggregation effect, we obtained a non-linear, quadratic dependence of this effect on lipophilicity, the optimum being at log P = 3.The antiaggregation effect increased with shortening the chain between the carbonyl and the carboxyl, and with increasing acidity.It was also diminished by the presence of a methyl group on the interlinking chain.To assess the role of lipophilicity we used the RM values of partition chromatography.The relation between anti-inflammatory efficacy and structure was assessed only qualitatively.In this aspect, too, the nature of the chain between the carbonyl and carboxyl proved to have a marked influence.The anti-inflammatory activity proved considerably enhanced by the presence of another aromatic ring in ω-oxoalkanoic acids derived from biphenyl.

Fenbufen, a new anti inflammatory analgesic: synthesis and structure activity relationships of analogs

100 analogs of fenbufen were prepared and tested using the carrageenan, polyarthritis, and UV erythema anti inflammatory tests and the 2 phenyl 1,4 benzoquinone writhing and inflamed paw pressure analgesic tests. Only 3 retained the same full spectrum of activity as fenbufen: dl 4 (4 biphenylyl) 4 hydroxybutyric acid, dl 4 (4 biphenylyl) 1,4 butanediol, and 4 biphenylacetic acid. Fenbufen had the same spectrum of activity as aspirin, phenylbutazone, and indomethacin in the 5 tests. In addition, dose response derived potencies show fenbufen more potent than aspirin and at least as potent as phenylbutazone in all 5 tests. Two related compounds were generally similar.