4053-51-4

Upstream product

• 351-28-0 N-(3-fluorophenyl)acetamide 
• 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 
• 588-16-9 m-methoxyacetanilide 
• 103-84-4 Acetanilid 
• 74097-24-8 N-(6',6'-dimethoxy-3'-oxocyclohexa-1',4'-dienyl)acetamide 
• 621-42-1 meta-hydroxyacetanilide 
• 93525-28-1 N-(2,5-dihydroxyphenyl)acetamide 
• 614-80-2 2-(acetylamino)phenol 

Downstream Products

• 2072-30-2 2-acetamido-5-bromo-1,4-benzoquinone 
• 72767-62-5 1H-benzindole-4,9-dione 
• 14422-99-2 2-(ethylamino)naphthalene-1,4-dione 

Relevant academic research and scientific papers

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 synthetic analogues: Preliminary exploration of their cytotoxic activity

In this study, we explore the cytotoxic activity of four natural abenquines (2a–d) and fourteen synthetic analogues (2e–j and 3a–h) against a panel of six human cancer cell lines using a SRB assay. It was found that most of the compounds revealed higher levels of cytotoxic activities than naturally occurring abenquines. The analogues carrying ethylpyrrolidinyl and ethylpyrimidinyl with either an acetyl group (2?h–i) or a benzoyl group (3f–g), were the most potent against all human cancer cell lines and displayed EC50 between a range of 0.6–3.4?μM. Notably, of the compounds tested, compound 2i proved the most cytotoxic against both ovarian (A2780) and breast (MCF7) cells, showing EC50?=?0.6 and 0.8?μM respectively. Likewise, the analogues 2i, 3f and 3?g showed strong activity against cell HT29 with EC50?=?0.9?μM for these compounds.

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.

Tailoring Natural Abenquines to Inhibit the Photosynthetic Electron Transport through Interaction with the D1 Protein in Photosystem II

Abenquines are natural N-acetylaminobenzoquinones bearing amino acid residues, which act as weak inhibitors of the photosynthetic electron transport chain. Aiming to exploit the abenquine scaffold as a model for the synthesis of new herbicides targeting photosynthesis, 14 new analogues were prepared by replacing the amino acid residue with benzylamines and the acetyl with different acyl groups. The synthesis was accomplished in three steps with a 68-95% overall yield from readily available 2,5-dimethoxyaniline, acyl chlorides, and benzyl amines. Key steps include (i) acylation of the aniline, (ii) oxidation, and (iii) oxidative addition of the benzylamino moiety. The compounds were assayed for their activity as Hill inhibitors, under basal, uncoupled, or phosphorylating conditions, or excluding photosystem I. Four analogues showed high effectiveness (IC50 = 0.1-0.4 μM), comparable with the commercial herbicide diuron (IC50 = 0.3 μM). The data suggest that this class of compounds interfere at the reducing side of photosystem II, having protein D1 as the most probable target. Molecular docking studies with the plastoquinone binding site of Spinacia oleracea further strengthened this proposal.

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.

Synthesis of amino-1,4-benzoquinones and their use in Diels - Alder approaches to the aminonaphthoquinone antibiotics

A new protocol for the synthesis of protected amino-1,4-benzoquinones by oxidation of the corresponding 2,5-dimethoxyaniline derivatives using PhI(OAc)2 or PhI- (OCOCF3)2 in water containing 2.5% methanol is reported. The process represents an improvement over previously reported methods, both in terms of yield and number of steps, and in the range of nitrogen protecting groups that it tolerates. A number of novel aminobenzoquinones were prepared and subsequently used as dienophiles in Diels - Alder reactions to (Figure presented) form building blocks for the synthesis of the aminonaphthoquinone antibiotics such as salinisporamycin.

Oxidation of anisoles to p-benzoquinone monoketals catalyzed by a ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane with tert-butyl hydroperoxide

A protocol based on [RuIII(Me3tacn)(CF 3CO2)2(H2O)]CF3CO 2 (1, Me3tacn = 1,4,7-trimethyl-1,4,7-triazacyclononane) as catalyst and tert-butyl hydroperoxide (TBHP) as oxidant was developed for oxidation of anisoles to p-benzoquinone monoketals. This reaction can be formally considered as regioselective aromatic C-H oxidation. With 2-methoxyanisole as substrate, 3,4-dimethoxy-4-tert-butoxy-2,5-cyclohexadienone can be obtained in up to 82% yield based on 84% substrate conversion.

Mechanistic diversity of the selective oxidations mediated by supported iron phthalocyanine complexes

Selective oxidations of (i) phenols and condensed aromatics to quinones and (ii) alkynes to α,β-acetylenic ketones mediated by supported iron phthalocyanine complexes exhibit very different mechanistic features as evidenced by 18O labelling and kinetic isotope effect studies. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.

Acetamidoquinone and acetamidohydroxy derivatives as inhibitors for both dihydroxyacetamido epoxidase and dehydrogenase

A series of monohydroxy and dihydroxyacetanilides, acetamidoquinones and bromoacetamidoquinones have been synthesised and tested as substrates and/or inhibitors of highly purified dihydroxyacetamido epoxidase (DHAE) and dihydroxy acetamido dehydrogenase (DHADH) from Streptomyces LL-C10337. None was found to act as substrates but many selectively inhibit the enzymes. Kinetic analysis has shown that all the compounds act as reversible competitive inhibitors with respect to the substrates 2,5-dihydroxyacetanilide and 2,3-epoxy-1,4-benzoquinone-5-acetanilide. Monohydroxy acetanilides showed weak inhibition to these enzymes compared to the dihydroxy derivatives while the more powerful inhibitors were the benzoquinoneacetanilide and its 5-bromo equivalent.

Iodine(V) reagents in organic synthesis. Part 2. Access to complex molecular architectures via Dess-Martin periodinane-generated o-imidoquinones

o-Imidoquinones, a rather rare class of compounds, are prepared from anilides by the action of Dess-Martin pedodinane (DMP) and water. Their chemistry has been extensively investigated and found to lead to p-quinones and polycyclic systems of diverse mole