54903-12-7

Usage

InChI:InChI=1/C14H9NO3/c16-13(9-4-2-1-3-5-9)10-6-7-11-12(8-10)18-14(17)15-11/h1-8H,(H,15,17)

Upstream product

• 59-49-4 2-Benzoxazolinone 
• 618-32-6 Benzoyl bromide 
• 455-32-3 benzoyl fluoride 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 153756-94-6 4-acetamidophenyl N-(4-benzoyl-2-hydroxyphenyl)carbamate 
• 13787-59-2 3-benzoyl-2(3H)-benzoxazolone 
• 65-85-0 benzoic acid 

Downstream Products

• 139101-54-5 6-Benzoyl-3-(2-pyridin-4-yl-ethyl)-3H-benzooxazol-2-one 
• 76752-01-7 3-(6-benzoyl-2-benzoxazolinon-3-yl)propanoic acid 
• 31684-63-6 4-amino-3-hydroxybenzophenone 
• 104837-20-9 6-Benzoyl-3-(4-phenyl-piperidin-1-ylmethyl)-3H-benzooxazol-2-one 
• 104837-19-6 6-Benzoyl-3-(4-hydroxy-4-phenyl-piperidin-1-ylmethyl)-3H-benzooxazol-2-one 
• 76751-96-7 (6-benzoyl-2-benzoxazolinon-3-yl)acetic acid 
• 128029-48-1 6-Benzoyl-3-[2-(4-bromo-phenyl)-2-oxo-ethyl]-3H-benzooxazol-2-one 
• 76752-06-2 2-(6-Benzoyl-2-oxo-benzooxazol-3-yl)-propionic acid ethyl ester 
• 353280-51-0 dimethyl 4-[2-(6-benzoyl-2(3H)-benzoxazolon-3-yl)ethoxy]benzylidenemalonate 
• 76752-11-9 2-(6-Benzoyl-2-oxo-benzooxazol-3-yl)-propionic acid 
• 99541-40-9 6-benzoyl-3-piperidinomethyl-2(3H)-benzoxazolone 

Relevant academic research and scientific papers

FeCl3-DMF complex as efficient catalyst for the synthesis of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones

FeCl3-DMF complex has been tested on Friedel-Crafts reaction of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone with acid chlorides and anhydrides as acylating agents. In these conditions, the 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones were obtained in yields ranging from 52 to 89%. Among the various commonly catalysts; AlCl3-DMF, ZnCl2-DMF and PPA, explored in this study, the best conditions using FeCl3-DMF were found the most convenient one

Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure-Activity Relationship (SAR) Studies

Ceramides are lipid-derived intracellular messengers involved in the control of senescence, inflammation, and apoptosis. The cysteine amidase, acid ceramidase (AC), hydrolyzes these substances into sphingosine and fatty acid and, by doing so, regulates their signaling activity. AC inhibitors may be useful in the treatment of pathological conditions, such as cancer, in which ceramide levels are abnormally reduced. Here, we present a systematic SAR investigation of the benzoxazolone carboxamides, a recently described class of AC inhibitors that display high potency and systemic activity in mice. We examined a diverse series of substitutions on both benzoxazolone ring and carboxamide side chain. Several modifications enhanced potency and stability, and one key compound with a balanced activity-stability profile (14) was found to inhibit AC activity in mouse lungs and cerebral cortex after systemic administration. The results expand our arsenal of AC inhibitors, thereby facilitating the use of these compounds as pharmacological tools and their potential development as drug leads.

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.

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.]

Aromatase inhibitor compounds and uses thereof

The invention concerns the use of a compound of formula (I) inhibitor of aromatase for the preparation of a pharmaceutical formulation intended for treatment of cancer or psoriasis. It equally relates to compounds of formula (I), notably for their use as active ingredients of a medication.

Unsymmetrical Diarylketones from Electron-rich Heterocyclic Arenes

AlCl3-mediated chlorocarbonylation of a first arene by oxalyl chloride followed by in situ Friedel-Crafts acylation of a second electron-rich arene expeditiously provides, in a one-pot procedure, either symmetrical or unsymmetrical benzophenones with yields ranging from 17-52%. Best results are obtained when the more activated substrate is used as the second arene. Another advantage is that the resultant benzophenone precipitates from the reaction mixture allowing facile workup.

Benzazole compounds and their use

The present invention discloses a method for repelling insects, mites and ticks from warm-blooded animals with a benzazole compound.

On the reaction of Meldrum's acid with N- trimethylsilylanilines substituted by electron withdrawing groups

The reaction of Meldrum's acid with silylated anilines substituted by an electron withdrawing group easily yields the corresponding N-phenyl malonamic acid, when the reaction is performed under high vacuum in dichlorobenzene.

Friedel-crafts acylation of 2(3H)-benzoxazolone: Investigation of the role of the catalyst and microwave activation

To study the scope and limitations of the use of complexed species of AlCl3 in Friedel-Crafts reactions, we investigated the acctylation and benzoylation of 2(3H)-benzoxazolone and 3-methyl-2(3H)-benzoxazolone varying the amide complexing agent. We replaced dimethylformamide by N-methylformamide, dimethylacetamide, pyrrolidone, N-methylpyrrolidone, tetramethylurea, and dimethylsulfoxide. However, there was no particular advantage of substituting dimethylformamide by another amide ligand. This can probably be ascribed to the fact that the complex formed between AlCl3 and the complexing agent becomes too stable. Alternatively, a route using polyphosphoric acid and microwave activation was explored. The major advantage of running the reaction in a microwave oven was that a good yield was reached in a rather short period of time.

'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.