76751-94-5

Upstream product

• 59-49-4 2-Benzoxazolinone 
• 74-11-3 para-chlorobenzoic acid 
• 13787-58-1 3-(4-chlorobenzoyl)-3H-1,3-benzoxazol-2-one 
• 122-01-0 4-chloro-benzoyl chloride 
• 790-41-0 4-chlorobenzoic anhydride 

Downstream Products

• 76752-02-8 3-[6-(4-Chloro-benzoyl)-2-oxo-benzooxazol-3-yl]-propionic acid 
• 123172-45-2 (4-Amino-3-hydroxy-phenyl)-(4-chloro-phenyl)-methanone 
• 76751-97-8 [6-(4-Chloro-benzoyl)-2-oxo-benzooxazol-3-yl]-acetic acid 
• 76752-07-3 2-[6-(4-Chloro-benzoyl)-2-oxo-benzooxazol-3-yl]-propionic acid ethyl ester 
• 116337-63-4 7-(4-Chloro-benzoyl)-4H-benzo[1,4]oxazin-3-one 
• 116337-65-6 7-(4-Chloro-benzoyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one 
• 116337-64-5 7-(4-Chloro-benzoyl)-2-methyl-4H-benzo[1,4]oxazin-3-one 
• 76752-12-0 2-[6-(4-Chloro-benzoyl)-2-oxo-benzooxazol-3-yl]-propionic acid 

Relevant academic research and scientific papers

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.

'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.

ACYLATION OF 2,3-DIHYDROBENZOXAZOL-2-ONE IN A TWO STEPS METHOD INVOLVING AN ACYL MIGRATION

A new method of acylation of 2,3-dihydrobenzoxazol-2-one 1 is proposed in a two-steps procedure involving an acyl migration.

Acyl-7 dihydro-2,3 benzoxazin-1,4 ones-3 et proprietes normolipemiantes

7-Acyl-2,3-dihydro-1,4-benzoxazin-3-ones and normolipemic properties.Fibrates are still among the most widely used drugs for the treatment of dyslipoproteinemia. 7-Acyl-2,3-dihydro-1,4-benzoxazin-3-ones (Fig.1B) can be considered as conformationally restrained analogues of fibrates, such as fenofibrate.These compounds have been prepared and studied for their normolipemic activity particularly on plasma cholesterol, triglyceride and high density lipoprotein (HDL) cholesterol levels.Hepatotoxicity and mutagenicity have also been evaluated.Some of them show an interesting activity, quite comparable to fenofibrate, and are devoid of hepatotoxicity. hyperlipidemia / hypocholesterolemic drugs / fibrates / 7-acyl-1,4-benzoxazin-3-ones