3809-93-6

Basic information

• Product Name: 2-Methyl-4H-pyrido[3,2-e][1,3]oxazin-4-one
• Synonyms: 2-Methyl-4H-pyrido[3,2-e][1,3]oxazin-4-one;2-Methyl-4H-pyrido[2,3-d][3,1]oxazin-4-one;2-methyl-4H-pyrido[2,3-d][1,3]oxazin-4-one
• CAS NO: 3809-93-6
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.14544
• Mol File: 3809-93-6.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Methyl-4H-pyrido[3,2-e][1,3]oxazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-4H-pyrido[3,2-e][1,3]oxazin-4-one(3809-93-6)
• EPA Substance Registry System: 2-Methyl-4H-pyrido[3,2-e][1,3]oxazin-4-one(3809-93-6)

Safety Data

• Hazardous Substances Data: 3809-93-6(Hazardous Substances Data)

Upstream product

• 59-67-6 nicotinic acid 
• 2398-81-4 Nicotinic acid N-oxide 
• 2942-59-8 2-chloronicotinic acid 
• 14667-47-1 methyl 2-aminonicotinate 
• 108-24-7 acetic anhydride 
• 5345-47-1 2-aminopyridin-3-carboxylic acid 

Downstream Products

• 54716-26-6 3-(4-chloro-phenyl)-2-methyl-3H-pyrido[2,3-d]pyrimidin-4-one 
• 76285-18-2 2-Methyl-3-phenethyl-3H-pyrido[2,3-d]pyrimidin-4-one 
• 94243-07-9 2-(p-Methoxystyryl)-3-phenylpyrido<2,3-d>pyrimidin-4(3H)-one 
• 94243-12-6 2-((E)-Styryl)-3-p-tolyl-3H-pyrido[2,3-d]pyrimidin-4-one 
• 94243-14-8 3-(4-Chloro-phenyl)-2-((E)-styryl)-3H-pyrido[2,3-d]pyrimidin-4-one 
• 94243-11-5 3-(4-Methoxy-phenyl)-2-((E)-styryl)-3H-pyrido[2,3-d]pyrimidin-4-one 
• 94243-08-0 3-Phenyl-2-((E)-2-p-tolyl-vinyl)-3H-pyrido[2,3-d]pyrimidin-4-one 
• 94243-10-4 2-[(E)-2-(4-Chloro-phenyl)-vinyl]-3-phenyl-3H-pyrido[2,3-d]pyrimidin-4-one 
• 94243-09-1 2-[(E)-2-(2-Nitro-phenyl)-vinyl]-3-phenyl-3H-pyrido[2,3-d]pyrimidin-4-one 
• 94243-13-7 3-(3-Nitro-phenyl)-2-((E)-styryl)-3H-pyrido[2,3-d]pyrimidin-4-one 
• 54716-27-7 2-Methyl-3-phenylpyrido<2,3-d>pyrimidin-4(3H)-one 
• 76285-14-8 3-(3-chloro-phenyl)-2-methyl-3H-pyrido[2,3-d]pyrimidin-4-one 
• 76285-13-7 3-(2-chlorophenyl)-2-methyl-pyrido<2,3-d>pyrimidin-4(3H)-one 
• 15511-44-1 2-Methyl-3-(2',4'-dimethylphenyl)-4-oxo-3,4-dihydropyrido<2,3-d>pyrimidin 

Relevant articles and documents

Reactions of 2-methyl-4H-pyrido[2,3-d][3,1]oxazin-4-one with active methylene compounds: A new efficient route to 3-substituted 4-hydroxy-1,8-naphthyridin-2(1H)-ones

3-Substituted 1,8-naphthyridine-2,4-diones, compounds of very important pharmaceutical use, have been synthesized using a new efficient route. The reaction of 2-methyl-4H-pyrido-[2,3-d][3,1]oxazin-4-one, 1b, with active methylene compounds furnishes the 1-acetyl-3-substituted-4-hydroxy-1,8-naphthyridin-2-ones 3-5, in good yields. In the case of cyanoacetic esters the intermediate C-acylation compounds 7 and 8 were isolated and subsequently cyclized to 1-acetyl-3-cyano-4-hydroxy-1,8-naphthyridin-2-one 6. Spectral data and physical characteristics for all compounds are reported.

Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C–O Bond Formation

Enantioselective Cu-catalyzed C–O cross coupling reactions yielding atropisomeric resorcinol-bearing quinazolinones have been developed. Utilizing a new guanidinylated dimeric peptidic ligand, a set of products were generated in good yields with excellent

Synthesis and evaluation of new quinazolin-4(3H)-one derivatives as potent antibacterial agents against multidrug resistant Staphylococcus aureus and Mycobacterium tuberculosis

Staphylococcus aureus and Mycobacterium tuberculosis are major causative agents responsible for serious nosocomial and community-acquired infections impacting healthcare systems globally. Over several decades, these pathogens have developed resistance to multiple antibiotics significantly affecting morbidity and mortality. Thus, these recalcitrant pathogens are amongst the most formidable microbial pathogens for which international healthcare agencies have mandated active identification and development of new antibacterial agents for chemotherapeutic intervention. In our present work, a series of new quinazolin-4(3H)-one derivatives were designed, synthesized and evaluated for their antibacterial activity against ESKAP pathogens and pathogenic mycobacteria. The experiments revealed that 4'c, 4'e, 4'f and 4'h displayed selective and potent inhibitory activity against Staphylococcus aureus with MIC values ranging from 0.03-0.25 μg/mL. Furthermore, compounds 4'c and 4'e were found to be benign to Vero cells (CC50 = >5 μg/mL) and displayed promising selectivity index (SI) > 167 and > 83.4 respectively. Additionally, 4'c and 4'e demonstrated equipotent MIC against multiple drug-resistant strains of S. aureus including VRSA, concentration dependent bactericidal activity against S. aureus and synergized with FDA approved drugs. Moreover, compound 4′c exhibited more potent activity in reducing the biofilm and exhibited a PAE of ～2 h at 10X MIC which is comparable to levofloxacin and vancomycin. In vivo efficacy of 4'c in murine neutropenic thigh infection model revealed that 4'c caused a similar reduction in cfu as vancomycin. Gratifyingly, compounds 4d, 4e, 9a, 9b, 14a, 4'e and 4'f also exhibited anti-mycobacterial activity with MIC values in the range of 2-16 μg/mL. In addition, the compounds were found to be less toxic to Vero cells (CC50 = 12.5->100 μg/mL), thus displaying a favourable selectivity index. The interesting results obtained here suggest the potential utilization of these new quinazolin-4(3H)-one derivatives as promising antibacterial agents for treating MDR-Staphylococcal and mycobacterial infections.