943994-74-9

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 2-(4-bromo-2-methyl-6-nitrophenoxy)acetate is used as an intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into complex molecular structures, contributing to the development of new drugs.
Used in Agrochemical Synthesis:
It is also used as an intermediate in the synthesis of agrochemicals, particularly due to its structural similarity to known compounds used in agriculture, such as pesticides or herbicides.
Used in Organic Synthesis:
Methyl 2-(4-bromo-2-methyl-6-nitrophenoxy)acetate is utilized as a versatile building block in organic synthesis, allowing for the creation of a wide range of complex molecules for various applications across different industries.

Upstream product

• 20294-50-2 4-bromo-2-methyl-6-nitrophenol 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 1221500-65-7 6-[5-(4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-yl]-8-methyl-2H-1,4-benzoxazin-3(4H)-one 
• 943994-87-4 8-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-1,4-benzoxazin-3(4H)-one 
• 121564-97-4 6-bromo-8-methyl-2H-1,4-benzoxazin-3(4H)-one 

Relevant academic research and scientific papers

Discovery of 6-[5-(4-fluorophenyl)-3-methyl-pyrazol-4-yl]-benzoxazin-3-one derivatives as novel selective nonsteroidal mineralocorticoid receptor antagonists

In the course of our study on selective nonsteroidal mineralocorticoid receptor (MR) antagonists, a series of novel benzoxazine derivatives possessing an azole ring as the core scaffold was designed for the purpose of attenuating the partial agonistic activity of the previously reported dihydropyrrol-2-one derivatives. Screening of alternative azole rings identified 1,3-dimethyl pyrazole 6a as a lead compound with reduced partial agonistic activity. Subsequent replacement of the 1-methyl group of the pyrazole ring with larger lipophilic side chains or polar side chains targeting Arg817 and Gln776 increased MR binding activity while maintaining the agonistic response at the lower level. Among these compounds, 6-[1-(2,2-difluoro-3-hydroxypropyl)-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl]-2H-1,4-benzoxazin-3(4H)-one (37a) showed highly potent in vitro activity, high selectivity versus other steroid hormone receptors, and good pharmacokinetic profiles. Oral administration of 37a in deoxycorticosterone acetate-salt hypertensive rats showed a significant blood pressure-lowering effect with no signs of antiandrogenic effects.

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)

FUSED HETEROCYCLIC COMPOUND AND USE THEREOF

The present invention relates to wherein each symbol is as defined in the specification. The compound has a superior mineral corticoidreceptorantagonistic action and is useful as an agent for the prophylaxis or treatment of hypertension, cardiac failure and the like, a compound having a fused heterocycle, or a prodrug thereof, or a salt thereof; and an agent for the prophylaxis or treatment of hypertension, cardiac failure and the like.