54903-11-6

Upstream product

• 59-49-4 2-Benzoxazolinone 
• 123-62-6 propionic acid anhydride 
• 33388-19-1 3-propionylbenzo[d]oxazol-2(3H)-one 
• 337913-25-4 phosphorus pentaoxide 
• 802294-64-0 propionic acid 
• 79-03-8 propionyl chloride 

Downstream Products

• 54903-18-3 6-(1-hydroxy-propyl)-3H-benzooxazol-2-one 
• 54903-52-5 4-Amino-3-hydroxypropiophenone 
• 54943-19-0 3-methyl-6-propionyl-3H-benzooxazol-2-one 
• 1346701-40-3 3-benzyl-6-propionyl-3H-benzoxazol-2-one 
• 1346701-41-4 methyl 2-[2-(3-benzyl-2-oxo-2,3-dihydro-benzoxazol-6-yl)-1-methyl-2-oxo-ethyl]pentanoate 
• 1346701-42-5 2-(2-(4-benzylamino-3-hydroxy-phenyl)-1-methyl-2-oxo-ethyl)pentanoic acid 
• 1266604-45-8 3-(3-methylbenzoyl)-6-propionyl-2(3H)-benzoxazolone 
• 1266604-43-6 3-(3-phenylpropionyl)-6-propionyl-2(3H)-benzoxazolone 
• 1266604-42-5 3-(phenylacetyl)-6-propionyl-2(3H)-benzoxazolone 
• 1266604-48-1 3-(4-nitrobenzoyl)-6-propionyl-2(3H)-benzoxazolone 
• 1266604-46-9 3-(4-methylbenzoyl)-6-propionyl-2(3H)-benzoxazolone 
• 1266604-44-7 3-benzoyl-6-propionyl-2(3H)-benzoxazolone 
• 1266604-47-0 3-(2-chlorobenzoyl)-6-propionyl-2(3H)-benzoxazolone 
• 81513-95-3 6-Propionyl-3-[4-(3-trifluoromethyl-phenyl)-piperazin-1-ylmethyl]-3H-benzooxazol-2-one 

Relevant academic research and scientific papers

BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS

The present invention relates to benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides benzoxazolone derivatives for use as a medicament in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

Discovery and optimization of novel fatty acid transport protein 1 (FATP1) inhibitors

The discovery, optimization and structure-activity relationship of novel FATP1 inhibitors have been described. The detailed SAR studies of each moiety of the inhibitors combined with metabolite analysis led to the identification of the potent inhibitors 1

PYRIDAZINONES AS GPR119 AGONISTS

The present invention relates to pyridazinone derivatives of general formula (I), wherein the groups A, G and R1 are as defined in the application, the tautomers thereof, stereoisomers thereof, the mixtures thereof and the salts thereof, which

Design and synthesis of 3-acyl-2(3H)-benzoxazolone and 3-acyl-2(3H)- benzothiazolone derivatives

A simpler and efficient "green" method using solid sodium hydroxide in a solvent mixture of acetone/water was found to catalyze N-acylation of 2(3H)-benzoxazolones and 2(3H)-benzothiazolones for facile and rapid synthesis of N-acyl derivatives in excellent yields. This method was applied to the synthesis of a series of 132 compounds employing a variety of acyl chlorides. Graphical abstract: [Figure not available: see fulltext.]

'Fries like' rearrangement: A novel and efficient method for the synthesis of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones

6-Acyl-2(3H)-benzoxazolone and 6-acyl-2(3H)-benzothiazolone derivatives have particularly interesting anti-inflammatory, antiepileptic, analgesic and antiviral properties. In this study, we report an original method of acylation on the 6-position of 2(3H)-banzoxazolone and 2(3H)benzothiazolone which consists in a two-step procedure involving migration of the acyl group from the N-position to the 6-position of the hetexocycle, at 165 °C and catalyzed by AlCl3. This new procedure was found to be more efficient with regard to the consumption of AICI3 and the yield (76-90%) than other acylation methods previously described.

Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)- benzothiazolone derivatives

A series of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives were synthesized and evaluated for anticonvulsant activity. The compounds were assayed, intraperitoneally in mice and per os in rats, against seizures induced by maximal electroshock (MES) and pentylene-tetrazole (scMet). Neurologic deficity was evaluated by the rotarod test. The compounds were prepared to determine the relationship between the 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives' structures and anticonvulsant activity. Several of these compounds showed significant anticonvulsant activity. Compounds 43 and 45 were the most active of the series against MES-induced seizures with ED50 values of 8.7 and 7.6 mg/kg, respectively. Compound 45 displayed good protection against MES-induced seizures and low toxicity in rats with an oral ED50 of 18.6 mg/kg and a protective index (PI = TD50/ED50) of 1 receptors with nanomolar affinities.

PROCESS FOR THE PREPARATION OF 6-(3,4-DIHYDRO-3-OXO-1,4(2H)-BENZOXAZIN-7-YL)-2,3,4,5-TETRAHYDROPYRIDAZIN-3-ONES

The invention relates to a process for the synthesis of compounds of the formula I, wherein R1-R5 are as defined herein. The process is a multistep process which comprises acylating a 2-benzoxazolinone with an alkanoic anhydride to form an acylated carbamate, hydrolyzing the carbamate, reacting the resultant aminophenol with haloalkanoyl halide to form a substituted benzoxazine, reacting the benzoxazine with an aldehyde, alkylating the resultant aminomethyl compound with an alkylating agent to form a quaternary ammonium salt, reacting the salt with an alkali metal cyanide to form a nitrile, hydrolyzing the nitrile and reacting the resultant carboxylic acid with hydrazine. The compounds are useful as cardiotonic and vasodilating agents and as inhibitors of phosphodiesterase fraction III and platelet aggregation. In addition, the compounds are active as smooth muscle relaxants and bronchodilators.

A Convenient and Efficient Method for the Preparation of 6-Acyl-2(3H)-benzoxazolones

Benzoxazolinone derivatives have been found to exhibit various pharmacological properties and 6-acyl-2(3H)-benzoxazolones are considered as key starting materials for the preparation of these compounds.Reported here are the optimal conditions for a regioselective acylation at the 6-position of the benzoxazolinone ring.A general method leading to the expected products in excellent yields consists in using a mixture of aluminum chloride-dimethylformamide as catalyst and acid anhydrides or chlorides as acylating agents.

Regioselectivity in the c-acylation of 2(3H)-benzoxazolones

Unequivocal synthetic routes towards 5- and 6-acyl-2(3H)-benzoxazolones are described. Comparison of the physicochemical properties of the compounds obtained by direct acylation under various Friedel-Crafts reaction conditions always leads to the conclusion that 6-acyl derivatives are the only isolated products. This observation contradicts previously published results.