161176-99-4

Basic information

• Product Name: 2-(2-HYDROXYETHYL)-2H-1,4-BENZOXAZIN-3(4H)-ONE
• Synonyms: 2-(2-HYDROXYETHYL)-2H-1,4-BENZOXAZIN-3(4H)-ONE
• CAS NO: 161176-99-4
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• Mol File: 161176-99-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2-HYDROXYETHYL)-2H-1,4-BENZOXAZIN-3(4H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-HYDROXYETHYL)-2H-1,4-BENZOXAZIN-3(4H)-ONE(161176-99-4)
• EPA Substance Registry System: 2-(2-HYDROXYETHYL)-2H-1,4-BENZOXAZIN-3(4H)-ONE(161176-99-4)

Safety Data

• Hazardous Substances Data: 161176-99-4(Hazardous Substances Data)

Upstream product

• 88-75-5 2-hydroxynitrobenzene 
• 58835-34-0 3-(2-nitrophenoxy)dihydrofuran-2-one 
• 5061-21-2 α-bromo-γ-butyrolactone 
• 95-55-6 2-amino-phenol 

Downstream Products

• 374626-86-5 [2-(2-{4-[2-(3,4-dichloro-phenyl)-ethyl]-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl}-ethoxy)-phenyl]-acetic acid methyl ester 
• 374108-46-0 (2-{2-[3-oxo-4-(4-trifluoromethyl-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester 
• 374626-92-3 (2-{2-[4-(3,4-difluoro-benzyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester 
• 374626-23-0 {2-[2-(4-benzo[1,3]dioxol-5-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-ethoxy]-phenyl}-acetic acid methyl ester 
• 374626-84-3 (2-{2-[4-(3,4-dichloro-benzyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester 
• 374626-54-7 3-(2-{2-[4-(4-chloro-benzyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-propionic acid methyl ester 
• 374626-08-1 (2-{2-[4-(4-methoxy-benzyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester 
• 374626-27-4 (2-{2-[4-(4-methyl-benzyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester 
• 374626-58-1 (3-{2-[4-(4-chloro-benzyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester 
• 374626-52-5 (2-{2-[4-(4-chloro-benzyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester 
• 374626-90-1 (2-{2-[4-(4-fluoro-benzyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester 

Relevant articles and documents

Benzoxazinones as PPARγ Agonists. 2. SAR of the Amide Substituent and In Vivo Results in a Type 2 Diabetes Model

A series of benzoxazinones has been synthesized and tested for PPARγ agonist activity. Synthetic approaches were developed to provide either racemic or chiral compounds. In vitro functional potency could be measured through induction of the aP2 gene, a target of PPARγ. These studies revealed that compounds with large aliphatic chains at the nitrogen of the benzoxazinone were the most potent. Substitution of the chain was tolerated and in many cases enhanced the in vitro potency of the compound. Select compounds were further tested for metabolic stability, oral bioavailability in rats, and efficacy in db/db mice after 11 days of dosing. In vivo analysis with 13 and 57 demonstrated that the series has potential for the treatment of type 2 diabetes.

Benzoxazinones as PPARγ agonists. Part 1: SAR of three aromatic regions

A series of benzoxazinones was synthesized as PPARγ agonists. The compounds were obtained in seven steps, and SAR was developed by variations to the core shown below. The compounds were tested as functional agonists in the induction of the aP2 gene in preadipocytes, and the most potent compound in the series has an EC50=0.51 μM. The potency was further confirmed through a PPAR-Gal4 construct. Efficacy has been demonstrated in the db/db mouse model of hyperglycemia.

The preparation of 2-hydroxyethyl-2,3-dihydro-2H-1,4-benzoxazin-3(4H)- one derivatives

An efficient synthesis of 2-hydroxyethyl-2,3-dihydro-2H-1,4-benzoxazin- 3(4H)-one derivatives is described using α-bromo-γ-butyrolactone as a bis- electrophile containing a latent hydroxyethyl functional group.