121564-96-3

Basic information

• Product Name: 6-BROMO-8-CHLORO-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE
• Synonyms: 6-BROMO-8-CHLORO-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE;6-broMo-8-chloro-3,4-dihydro-2H-1,4-benzoxazin-3-one;6-Bromo-8-chloro-2H-1,4-benzoxazin-3(4H)-one
• CAS NO: 121564-96-3
• Molecular Formula: C8H5BrClNO2
• Molecular Weight: 262.49
• Mol File: 121564-96-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-BROMO-8-CHLORO-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-8-CHLORO-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE(121564-96-3)
• EPA Substance Registry System: 6-BROMO-8-CHLORO-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE(121564-96-3)

Safety Data

• Hazardous Substances Data: 121564-96-3(Hazardous Substances Data)

Upstream product

• 58349-01-2 4-bromo-6-chloro-2-nitrophenol 
• 943994-32-9 methyl 2-(4-bromo-2-chloro-6-nitrophenoxy)acetate 
• 79-07-2 Chloroacetamide 

Downstream Products

• 1454580-56-3 8-chloro-6-[4-(4-fluorophenyl)-2-methyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl]-2H-1,4-benzoxazin-3(4H)-one 
• 1454580-54-1 8-chloro-6-[4-(4-fluorophenyl)-1-(4-methoxybenzyl)-2-methyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl]-2H-1,4-benzoxazin-3(4H)-one 
• 943994-43-2 8-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-1,4-benzoxazin-3(4H)-one 

Relevant articles and documents

Identification of benzoxazin-3-one derivatives as novel, potent, and selective nonsteroidal mineralocorticoid receptor antagonists

Mineralocorticoid receptor (MR) blockade has come into focus as a promising approach for the treatment of cardiovascular diseases such as hypertension and congestive heart failure. In order to identify a novel class of nonsteroidal MR antagonists that exhibit significant potency and good selectivity over other steroidal hormone receptors, we designed a novel series of benzoxazin-3-one derivatives and synthesized them from 6-(7H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazin-6-yl)-2H-1,4-ben-zoxazin-3(4H)-one (1a), high-throughput screening (HTS) hit compound. Our design was based on a crystal structure of an MR/compound complex and a docking model. In the course of lead generation from 1a, a 1,2-diaryl framework was characterized as a key structure with high binding affinity. On the basis of scaffold hopping and optimization studies, benzoxazin-3-one derivatives possessing 1-phenyl-3-trifluoromethylpyrazol-5-yl moiety at the 6-position were identified as a novel series of potent and selective MR antagonists. Among these compounds, 6-[1-(4-fluoro-2-methylphenyl)- 3-(trifluoromethyl)-1H-pyrazol-5-yl]-2H-1,4-benzoxazin-3(4H)-one (14n) showed highly potent activity and good selectivity and also exhibited a significant antihypertensive effect in deoxycorticosterone acetate-salt hypertensive rats. On the basis of these results, compound 14n was progressed for further pharmacological evaluation. (Figure presented)

Synthesis of some 2(H),4(H)-1,2,4-triazino[3,4-c]-1,4-benzoxazin-5-ones

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