63471-85-2

Usage

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

Upstream product

• 108-30-5 succinic acid anhydride 
• 7446-70-0 aluminium trichloride 
• 101-81-5 Diphenylmethane 
• 98-95-3 nitrobenzene 

Downstream Products

• 147862-73-5 4-(diphenylmethylene)-n-butanoic acid 
• 18908-85-5 4-{4-[4-(4-{4-[4-(3-Carboxy-propionyl)-benzyl]-benzoyl}-benzoyl)-benzyl]-phenyl}-4-oxo-butyric acid 
• 221656-58-2 N,N-dimethyl-4-(diphenylmethylene)-n-butanamine 
• 221656-57-1 N,N-dimethyl-4-(diphenylmethylene)-n-butanamide 
• 1094213-90-7 (RS)-5-(4-benzylphenyl)dihydrofuran-2(3H)-one 
• 1094596-25-4 C₁₇H₁₈O₃ 
• 1356067-53-2 (+/-)-oxiran-2-ylmethyl 4-(4-benzylphenyl)butanoate 
• 1356067-57-6 (+/-)-tetrahydro-2H-pyran-2-ylmethyl 4-(4-benzylphenyl)butanoate 
• 18908-77-5 4-(4-Benzyl-phenyl)-4-oxo-butyric acid methyl ester 
• 63472-00-4 3-Brom-3-(4-Benzylbenzoyl)propionsaeure 
• 36330-88-8 3-(4-Benzoylbenzoyl)propionsaeure 

Relevant academic research and scientific papers

Synthesis, anti-convulsant activity and molecular docking study of novel thiazole pyridazinone hybrid analogues

Pyridazinone analogues have been known to be potential candidates for anticonvulsant agents. We have identified several pyridazinone-based anticonvulsant agents. As a continuation to our previous research, a series of hybrid pyridazinone-thiazole connected through amide linkage were designed and synthesized. Among these, compound SP-5F demonstrated significant anticonvulsant activity with median effective dose of 24.38 mg/kg (MES) and 88.23 mg/kg (scPTz). Results of GABA estimation showed a marked increase in the GABA level when compared with control. Molecular docking studies at the active site of GABA receptor, further confirmed the GABA modulatory effects of SP-5F.

Design, Synthesis, and Pharmacological Screening of Pyridazinone Hybrids as Anticonvulsant Agents

A series of new hybrid benzimidazole containing pyridazinones derivatives were designed and synthesized in accordance with the pharmacophoric requirements essential for the anticonvulsant activity. The synthesized compounds were evaluated for anticonvulsant activity on mice by the gold standard maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ)-induced seizure models. Among the compounds tested, SS-4F showed significant anticonvulsant activity in both the screens with ED50 values of 25.10 and 85.33 mg/kg in the MES and scPTZ screens, respectively. Compound SS-4F emerged as safer and effective anticonvulsant due to its several-fold higher protective indices. Further, the gamma-aminobutyric acid (GABA) estimation result showed a marked increase in the GABA level (1.7-fold) as compared to the control, which was further confirmed by good binding properties with the GABAA receptor.

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.

Novel high-affinity and selective biaromatic 4-substituted γ-hydroxybutyric acid (GHB) analogues as GHB ligands: Design, synthesis, and binding studies

γ-Hydroxybutyrate (GHB) is a metabolite of γ-aminobutyric acid (GABA) and has been proposed to function as a neurotransmitter or neuromodulator. GHB is used in the treatment of narcolepsy and is a drug of abuse. GHB binds to both GABAB receptors and specific high-affinity GHB sites in brain, of which the latter have not been linked unequivocally to function, but are speculated to be GHB receptors. In this study, a series of biaromatic 4-substituted GHB analogues, including 4′-phenethylphenyl, 4′-styrylphenyl, and 4′-benzyloxyphenyl GHB analogues, were synthesized and characterized pharmacologically in a [3H](E,RS)-(6,7, 8,9-tetrahydro-5-hydroxy-5H-benzocyclohept-6-ylidene)acetic acid ([ 3H]NCS-382) binding assay and in GABAA and GABA B receptor binding assays. The compounds were selective for the high-affinity GHB binding sites and several displayed Ki values below 100 nM. The affinity of the 4-[4′-(2-iodobenzyloxy)phenyl] GHB analogue 17b was shown to reside predominantly with the R-enantiomer (Ki = 22 nM), which has higher affinity than previously reported GHB ligands.

Syntheses and antiinflammatory activity of some 6-aryl-2,3,4,5-tetrahydro-3-pyridazinones

6-Aryl-2, 3, 4, 5-tetrahydro-3-pyridazinones (2c-22c) are obtained by dehydrocyclisation of various hydrazides formed by the reaction of appropriate methyl β-aroylpropionate and hydrazine hydrate in the presence of anhydrous sodium acetate. They show promising antiinflammatory activity during their evaluation by carrageenin induced paw edema test in rats.

Zwitterionic sulfobetaine inhibitors of squalene synthase

A substantial number of sulfobetaines (e.g., 10) have been synthesized and evaluated as inhibitors of squalene synthase (SS) on the basis of the idea that their zwitterionic structure would have properties conducive both to binding in the active site and to passage through cell membranes. When the simple sulfobetaine moiety is incorporated into compounds containing hydrophobic portions like those in farnesyl diphosphate (1) or presqualene diphosphate (2), inhibition of SS in a rat liver microsomal assay was indeed observed. For example, farnesylated sulfobetaine 10 has IC50 = 10 μM and aromatic derivative 35 has IC50 = 2 μM for SS inhibition. A wide variety of structural modifications, exemplified by compounds 43, 52, 76, 85, 91, 99, 111, and 115, was investigated. Unfortunately, no inhibitors in the submicromolar range were discovered, and exploration of a different type of zwitterion seems necessary if this appealing approach to inhibition of SS is going to provide a potential antihypercholesterolemic agent.

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.