690632-05-4

Basic information

• Product Name: TERT-BUTYL 6-BROMO-4-OXO-3,4-DIHYDRO-1'H-SPIRO[1,3-BENZOXAZINE-2,4'-PIPERIDINE]-1'-CARBOXYLATE
• Synonyms: 6-BROMOSPIRO[1,3-BENZOXAZINE-2,4'-PIPERIDINE]-4(3H)-ONE, N-BOC PROTECTED;TERT-BUTYL 6-BROMO-4-OXO-3,4-DIHYDRO-1'H-SPIRO[1,3-BENZOXAZINE-2,4'-PIPERIDINE]-1'-CARBOXYLATE;6-Bromospiro[1,3-benzoxazine-2,4'-piperidine]-4(3H)-one, N-BOC protected 95%;tert-Butyl 6-bromo-3,4-dihydro-4-oxo-1'H-spiro[1,3-benzoxazine-2,4'-piperidine]-1'-carboxylate;tert-Butyl 6-broMo-4-oxo-3,4-dihydrospiro[benzo[e][1,3]oxazine-2,4'-piperidine]-1'-carboxylate;6-Bromospiro[1,3-benzoxazine-2,4'-piperidine]-4(3H)-one,N-BOCprotected95%
• CAS NO: 690632-05-4
• Molecular Formula: C17H21BrN2O4
• Molecular Weight: 397.26
• Mol File: 690632-05-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 226 °C
• Boiling Point: 571.5 °C at 760 mmHg
• Flash Point: 299.4 °C
• Appearance: /
• Density: 1.49 g/cm³
• CAS DataBase Reference: TERT-BUTYL 6-BROMO-4-OXO-3,4-DIHYDRO-1'H-SPIRO[1,3-BENZOXAZINE-2,4'-PIPERIDINE]-1'-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 6-BROMO-4-OXO-3,4-DIHYDRO-1'H-SPIRO[1,3-BENZOXAZINE-2,4'-PIPERIDINE]-1'-CARBOXYLATE(690632-05-4)
• EPA Substance Registry System: TERT-BUTYL 6-BROMO-4-OXO-3,4-DIHYDRO-1'H-SPIRO[1,3-BENZOXAZINE-2,4'-PIPERIDINE]-1'-CARBOXYLATE(690632-05-4)

Safety Data

• Hazard Codes: C
• Hazardous Substances Data: 690632-05-4(Hazardous Substances Data)

Usage

General Description

Tert-butyl 6-bromo-4-oxo-3,4-dihydro-1'H-spiro[1,3-benzoxazine-2,4'-piperidine]-1'-carboxylate is a complex organic compound with the molecular formula C20H26BrNO4. It is a spirocyclic chemical that contains a benzoxazine and piperidine ring system. TERT-BUTYL 6-BROMO-4-OXO-3,4-DIHYDRO-1'H-SPIRO[1,3-BENZOXAZINE-2,4'-PIPERIDINE]-1'-CARBOXYLATE is commonly used in organic synthesis and medicinal chemistry research, as it has potential pharmacological properties. However, due to its complex structure and potential reactivity, it should be handled and used with caution in a controlled laboratory setting.

Upstream product

• 6329-74-4 5-bromo-2-hydroxybenzamide 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 

Downstream Products

• 1445145-54-9 C₂₃H₂₃FN₂O₄ 
• 1192128-27-0 (E)-3-(1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl)-acrylic acid methyl ester 
• 1192129-06-8 C₃₄H₃₇N₃O₅ 
• 1192129-16-0 C₃₅H₃₉N₃O₅ 
• 1192129-15-9 C₃₀H₃₀N₂O₄ 
• 1445145-66-3 C₃₁H₃₂N₂O₄ 
• 1192129-05-7 C₂₉H₂₈N₂O₄ 
• 1192129-04-6 C₃₀H₃₀N₂O₄ 
• 1192129-09-1 C₂₈H₃₃N₃O₅ 
• 1192129-08-0 C₂₃H₂₄N₂O₄*ClH 
• 1192129-07-9 C₂₄H₂₆N₂O₄ 
• 1192127-66-4 C₂₃H₂₄N₂O₄*ClH 
• 1192129-11-5 C₃₂H₃₉N₃O₇ 
• 1192129-10-4 C₂₇H₃₀N₂O₆ 

Relevant articles and documents

Synthesis and biological characterization of spiro[2H-(1,3)-benzoxazine-2, 4′-piperidine] based histone deacetylase inhibitors

Histone Deacetylases (HDACs) have become important targets for the treatment of cancer and other diseases. In previous studies we described the development of novel spirocyclic HDAC inhibitors based on the combination of privileged structures with hydroxamic acid moieties as zinc binding group. Herein, we report further explorations, which resulted in the discovery of a new class of spiro[2H-(1,3)-benzoxazine-2,4′-piperidine] derivatives. Several compounds showed good potency of around 100 nM and less in the HDAC inhibition assays, submicromolar IC50 values when tested against tumour cell lines and a remarkable stability in human and mouse microsomes. Two representative examples exhibited a good pharmacokinetic profile with an oral bioavailability equal or higher than 35% and one of them studied in an HCT116 murine xenograft model showing a robust tumour growth inhibition. In addition, the two benzoxazines were found to have a minor affinity for the hERG potassium channel compared to their corresponding ketone analogues.