36330-85-5

Usage

Uses

Used in Medical Applications:
Fenbufen is used as a cyclo-oxygenase inhibitor for its anti-inflammatory and analgesic effects. It helps in reducing pain and inflammation, making it a common choice for various medical applications.
Used in Antipyretic Applications:
Fenbufen is used as an antipyretic to reduce fever. Its ability to inhibit the production of prostaglandins, which are involved in the regulation of body temperature, makes it effective in lowering elevated body temperatures.
Used in Muscle Relaxation:
Fenbufen is used as a muscle relaxant, specifically for smooth muscles. Its anti-inflammatory properties help in reducing muscle spasms and providing relief from discomfort associated with muscle tension.

Originator

Cinopal,Cyanamid,Italy,1976

Manufacturing Process

135 g of aluminum chloride is dissolved in 500 ml of nitrobenzene, the solution being held below 10°C by external cooling. A finely ground mixture of 50 g of succinic anhydride and 75 g of biphenyl is added to the stirred solution, the temperature being held below 10°C. It is then held at room temperature for four days. After pouring the reaction mixture into a solution of 150 ml of concentrated hydrochloric acid in 1 liter of ice water, the nitrobenzene is removed by steam distillation. The solid is collected, dissolved in 4 liters of 3% hot sodium carbonate solution, clarified, and reprecipitated by the addition of excess 6N sulfuric acid solution. The crude product is collected, dried, and recrystallized from ethanol to give the pure subject compound, MP 185°C to 187°C.

Therapeutic Function

Antiinflammatory

Safety Profile

Poison by ingestion,intraperitoneal, and subcutaneous routes. Human systemiceffects by ingestion: cough, sweating, body temperature.An experimental teratogen. Other experimentalreproductive effects. An anti-inflammatory agent. Whenheated to decomposi

InChI:InChI=1/C16H14O3/c17-15(10-11-16(18)19)14-8-6-13(7-9-14)12-4-2-1-3-5-12/h1-9H,10-11H2,(H,18,19)/p-1

Upstream product

• 108-30-5 succinic acid anhydride 
• 92-52-4 biphenyl 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 1230-54-2 ethyl 4-(4-phenylphenyl)-4-oxobutyrate 
• 35288-13-2 3-(4-cyclohexylbenzoyl)propionic acid 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 6057-60-9 4-(4-phenylphenyl)butanoic acid 
• 54011-27-7 methyl 4-([1,1'-biphenyl]-4-yl)-4-oxobutanoate 
• 108-86-1 bromobenzene 
• 56216-10-5 methyl 3-([1,1'-biphenyl]-4-yl)-3-oxopropanoate 
• 92-91-1 biphenyl-4-acetaldehyde 
• 591-50-4 iodobenzene 

Downstream Products

• 92-92-2 biphenyl-4-carboxylic acid 
• 41526-73-2 7-phenyl-3,4-dihydronaphthalen-1(2H)-one 
• 63472-14-0 5-([1,1'-biphenyl]-4-yl)-5-methyldihydrofuran-2(3H)-one 
• 40977-08-0 5-biphenyl-4-yl-3H-furan-2-one 
• 124-38-9 carbon dioxide 
• 63472-16-2 3-(4-Phenylbenzoyl)propionsaeure-p-chloranilid 
• 113231-60-0 5-Biphenyl-4-yl-3-[1-(2-hydroxy-phenyl)-meth-(Z)-ylidene]-3H-furan-2-one 
• 63472-01-5 C₁₉H₂₂N₄O₂*ClH 
• 3218-36-8 4-Phenylbenzaldehyde 
• 264199-97-5 5-Biphenyl-4-yl-3-[1-(2-chloro-phenyl)-meth-(Z)-ylidene]-3H-furan-2-one 
• 264199-98-6 5-Biphenyl-4-yl-3-[1-(2-bromo-phenyl)-meth-(Z)-ylidene]-3H-furan-2-one 
• 496861-83-7 Acetic acid 4-[5-biphenyl-4-yl-2-oxo-furan-(3E)-ylidenemethyl]-2-methoxy-phenyl ester 
• 496861-77-9 Acetic acid 2-acetoxy-5-[5-biphenyl-4-yl-2-oxo-furan-(3E)-ylidenemethyl]-phenyl ester 
• 496861-78-0 5-Biphenyl-4-yl-3-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-3H-furan-2-one 

Relevant academic research and scientific papers

Phospholipid bicelles that align with their normals parallel to the magnetic field

We have recently reported phospholipid bicelles (bilayered micelles) that have positive anisotropy of the magnetic susceptibility and align with their normals parallel to an external magnetic field [J. Am. Chem. Soc. 2001, 123, 1537]. Improvements have been made via the synthesis of a new phospholipid, 1-dodecanoyl-2-(4-(4-biphenyl)butanoyl)-sn-glycero-3-phosphocholine (DBBPC). Bicelles can be formed by mixing DBBPC with a short-chain phospholipid, 1,2-dihexanoyl-sn-glycero-3-phosphocholine (DHPC) in a ratio between 5.1:1 and 6.5:1 in an aqueous medium. The 31P NMR spectra clearly show that these bicelles align with their principal axes parallel to the magnetic field within a wide temperature range. The 31P chemical shifts indicate that the conformation of the polar headgroup in these bicelles may be different from that in common bicelles. The phase behavior of a mixture of DBBPC/DHPC with 6:1 mole ratio was investigated in the temperature range of 10-75 °C using 31P, 2H, and 23Na NMR. At lower temperatures (10-54 °C), the system is dominated by the bicellar phase. At higher temperatures (54-75 °C), isotropic micelles are formed and coexist with the bicelles. The partial alignment of maltotriose in the DBBPC/ DHPC system was studied at three temperatures, and the 1H-13C dipolar coupling constants are compared with those obtained for two other bicelle solutions.

Nickel- and Palladium-Catalyzed Cross-Coupling of Stibines with Organic Halides: Site-Selective Sequential Reactions with Polyhalogenated Arenes

Herein, we disclose a general and efficient method for the synthesis of Sb-aryl and Sb-alkyl stibines by the nickel-catalyzed cross-coupling of halostibines with organic halides. The synthesized Sb-aryl stibines couple with aryl halides to give biaryls efficiently via palladium catalysis. Sequential reactions of stibines with polyhalogenated arenes bearing active C–I/C–Br sites and inactive C–Cl sites successfully proceeded, resulting in the formation of a variety of complex molecules with good site selectivity. Drugs such as diflunisal and fenbufen, as well as a fenofibrate derivative, were synthesized on gram scales in good yields, together with the high recovery of chlorostibine. Furthermore, catalytic mechanisms are proposed based on the results of control experiments.

Pd Nanoparticles Embedded Into MOF-808: Synthesis, Structural Characteristics, and Catalyst Properties for the Suzuki–Miyaura Coupling Reaction

Abstract: A heterogeneous single-site catalyst Pd@MOF-808 was successfully synthesized by water-based, green synthesis procedure. The catalytic experiments exhibited the Pd@MOF-808 promoted efficiently the Suzuki–Miyaura coupling reaction without the assistance of organic phosphine ligands at atmospheric pressure conditions. The catalyst also could be applied in the gram-scale synthesis of industrially anti-inflanmatory analgestic Fenbufen. Graphic Abstract: [Figure not available: see fulltext.]

Multi-Targeting Tacrine Conjugates with Cholinesterase and Amyloid-Beta Inhibitory Activities: New Anti-Alzheimer's Agents

Alzheimer's disease (AD) is a severe age dependent and chronic problem with no cure so far. The available treatments are temporary, acting over short period of time. The main pathological hallmark of the disease includes cholinergic dysfunction, oxidative stress, accumulation of Aβ fibrils and tau tangles. In context with the multi-factorial nature of this disease, two different series of molecules were developed to hit the multifactorial disease targets. Mainly, the molecules were designed to inhibit the AChE and aggregation of Aβ, and also oxidative damage. Two novel series of TAC-fenbufen/menbutone conjugated molecules were designed, synthesized and bio-assayed. All compounds showed inhibition capacity towards AChE, Aβ aggregation and moderate to good radical scavenging capacity. Particularly, five TAC-menbutone molecules showed improved AChE and Aβ aggregation inhibition capacity compared to TAC-fenbufen conjugated molecules. Overall, these novel series of molecules may be potential drug lead molecules in the treatment of AD.

Enantioselective decarboxylative Mannich reaction of β-keto acids withC-alkynylN-BocN,O-acetals: access to chiral β-keto propargylamines

The chiral keto-substituted propargylamines are an essential class of multifunctional compounds in the field of organic and pharmaceutical synthesis and have attracted considerable attention, but the related synthetic approaches remain limited. Therefore, a concise and efficient method for the enantioselective synthesis of β-keto propargylaminesviachiral phosphoric acid-catalyzed asymmetric Mannich reaction between β-keto acids andC-alkynylN-BocN,O-acetals as easily availableC-alkynyl imine precursors has been demonstrated here, affording a broad scope of β-ketoN-Boc-propargylamines in high yields (up to 97%) with generally high enantioselectivities (up to 97?:?3 er).

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.

A Convoluted Polyvinylpyridine-Palladium Catalyst for Suzuki-Miyaura Coupling and C?H Arylation

The development of highly active and reusable supported catalysts for Suzuki-Miyaura coupling and catalytic C?H arylation is important for fundamental and applied chemistry, with these reactions being used to produce medical compounds and functional materials. Herein, we found that a mesoporous composite made of a linear poly(4-vinylpyridine) and tetrachloropalladate acted as a dual-mode catalyst for a variety of cross-coupling reactions, with both Pd nanoparticles and a Pd complex catalyst being observed under different conditions. The polyvinylpyridine-palladium composite 1 was readily prepared via the molecular convolution of poly(4-vinylpyridine) and sodium tetrachloropalladate to provide a hardly soluble polymer-metal composite. The Suzuki-Miyaura coupling and the C?H arylation of aryl chlorides and bromides with arylboronic acids, thiophenes, furans, benzene, and anisole proceeded in the presence of 0.004 mol% (40 mol ppm) to 1 mol% Pd of 1 to afford the corresponding coupling products in high yields. Furthermore, the catalyst was reused without an appreciable loss of activity. Pharmaceutical compounds and functional materials were synthesized via the coupling reactions. N2 gas adsorption/desorption analysis indicated that the catalyst had a mesoporous nature, which played a crucial role in the catalysis. In the Suzuki-Miyaura couplings, in situ generated palladium nanoparticles in the polymer matrix were catalytically active, while a polymeric Pd(II) complex was crucial in the C?H arylations. These catalytic species were investigated via XAFS, XPS, far-infrared absorption, and Raman spectroscopies, as well as DFT calculations. (Figure presented.).

Intermolecular Reductive Heck Reaction of Unactivated Aliphatic Alkenes with Organohalides

A general intermolecular reductive Heck reaction of organohalides with both terminal and internal unactivated aliphatic alkenes has been first realized in high yield with complete anti-Markovnikov selectivity. The challenging vinyl bromides, aryl chlorides, and polysubstituted internal alkenes were first applied. More than 100 remote carbofunctionalized alkyl carboxylic acid derivatives were rapidly synthesized from easily accessible starting materials. The synthesis of drug molecules has further demonstrated the wide synthetic utility of this scalable strategy. Preliminary mechanistic studies are consistent with the proposed catalytic cycle.

Visible-light-induced oxidation/[3 + 2] cycloaddition/oxidative aromatization to construct benzo[ a]carbazoles from 1,2,3,4-tetrahydronaphthalene and arylhydrazine hydrochlorides

An efficient synthesis of benzo[a]carbazoles via visible-light-induced tandem oxidation/[3 + 2] cycloaddition/oxidative aromatization reactions was reported. The benzylic C(sp3)-H of tetrahydronaphthalene was activated through visible-light photoredox catalyst with oxygen as the clean oxidant under mild reaction conditions. This protocol proceeds efficiently with broad substrate scope, and the mechanism study was performed.

Synthesis method of Fenbufen

The invention discloses a synthesis method of Fenbufen. The synthesis method comprises the following steps: uniformly mixing raw materials of N-(oct-aminoquinoline) butyl-3-enamide, 4-bromobiphenyl and so on with anhydrous 2, 3-butanediol and performing a drastic stirring reaction on the mixture in an oil bath at the temperature of 125-135 DEG C for 12h, so as to obtain a compound with a guiding group; adding the compound into an ethanol solvent containing sodium hydroxide for heating reflux, so as to obtain biphenyl butyrate; mixing biphenyl butyrate, p-toluenesulfonic acid and methanol for heating reflux, so as to obtain biphenyl methyl butyrate; adding biphenyl methyl butyrate and potassium peroxomonosulfate into nitromethane, then adding potassium bromide, performing a reaction at thetemperature of 50 DEG C, adding sodium hydroxide for reflux acidification, so as to obtain Fenbufen. According to the synthesis method, the problem that a synthesis process of the existing Fenbufen has excessive steps is effectively solved; additionally, the synthesis method has the characteristics of being high in reaction regioselectivity and yield, mild in reaction conditions and simple in reaction and aftertreatment purification processes.