4053-51-4

Basic information

• Product Name: Acetamide, N-(3,6-dioxo-1,4-cyclohexadien-1-yl)-
• CAS NO: 4053-51-4
• Molecular Formula: C8H7NO3
• Molecular Weight: 165.148
• Mol File: 4053-51-4.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: Acetamide, N-(3,6-dioxo-1,4-cyclohexadien-1-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamide, N-(3,6-dioxo-1,4-cyclohexadien-1-yl)-(4053-51-4)
• EPA Substance Registry System: Acetamide, N-(3,6-dioxo-1,4-cyclohexadien-1-yl)-(4053-51-4)

Safety Data

• Hazardous Substances Data: 4053-51-4(Hazardous Substances Data)

Upstream product

• 614-80-2 2-(acetylamino)phenol 
• 621-42-1 meta-hydroxyacetanilide 
• 588-16-9 m-methoxyacetanilide 
• 92959-62-1 2,4-diacetamidophenyl acetate 
• 75258-07-0 1,2-diacetamido-4-acetoxybenzene 
• 137-09-7 2,4-diaminophenol dihydrochloride 
• 51-28-5 2,4-Dinitrophenol 
• 102-56-7 2,5-dimethoxyaniline 
• 93-26-5 2-methoxyacetanilide 
• 3467-59-2 2,5-dimethoxyacetanilide 
• 103-84-4 Acetanilid 
• 74097-24-8 N-(6',6'-dimethoxy-3'-oxocyclohexa-1',4'-dienyl)acetamide 
• 93525-28-1 N-(2,5-dihydroxyphenyl)acetamide 
• 75258-08-1 1-hydroxy-3,4-diacetamidobenzene 

Downstream Products

• 615-94-1 2,5-dihydroxy-1,4-benzoquinone 
• 124251-44-1 5-anilino-2-hydroxy-1,4-benzoquinone 
• 72767-62-5 1H-benzindole-4,9-dione 
• 14422-99-2 2-(ethylamino)naphthalene-1,4-dione 

Relevant articles and documents

Tertiary amines as vinyl source for the formations of aryl or pyrrole ring on amido-substitued 1,4-quinone with the assistance of palladium salt

The one-pot synthesis of 3-isopropyl-6-methyl-1H-benzo[f]indole-4,9-dione (3e), N-(4-[isopentylamino]-3,6-dioxocyclohexa-1,4-dien-1-yl)acetamide (4d), 2-(isopentylamino)-6-methylnaphthalene-1,4-dione (5b), and 2-(4-acetamido-3,6-dioxocyclohexa-1,4-dien-1-

Natural Abenquines and Their Synthetic Analogues Exert Algicidal Activity against Bloom-Forming Cyanobacteria

Abenquines are natural quinones, produced by some Streptomycetes, showing the ability to inhibit cyanobacterial growth in the 1 to 100 μM range. To further elucidate their biological significance, the synthesis of several analogues (4f-h, 5a-h) allowed us to identify some steric and electronic requirements for bioactivity. Replacing the acetyl by a benzoyl group in the quinone core and also changing the amino acid moiety with ethylpyrimidinyl or ethylpyrrolidinyl groups resulted in analogues 25-fold more potent than the natural abenquines. The two most effective analogues inhibited the proliferation of five cyanobacterial strains tested, with IC50 values ranging from 0.3 to 3 μM. These compounds may be useful leads for the development of an effective strategy for the control of cyanobacterial blooms.

First total synthesis and phytotoxic activity of Streptomyces sp. metabolites abenquines

The first total synthesis of abenquines A, B2, C and D has been achieved in three steps starting from commercially available 2,5-dimethoxyaniline, with overall yields of 41-61%. Four analogues bearing the amino acids d-valine (17), l-methionine (18), and glycine (19), and benzylamine (20), were also prepared in 45-72% yield. The inhibitory properties of these compounds were evaluated against the photoautotrophic growth of a model Synechococcus sp. strain. Abenquine C and its enantiomer were substantially ineffective, whereas all other abenquines significantly inhibited cell proliferation, with concentrations causing 50%-inhibition of algal growth ranging from 10-5 to 10-6 M.