16281-43-9

Usage

Uses

Used in Pharmaceutical Industry:
1-Oxo-3-methyl-8-hydroxy-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid is used as an intermediate in the synthesis of Ochratoxin B (O148500), a toxic metabolite produced by Aspergillus ochraceus. 1-Oxo-3-methyl-8-hydroxy-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid plays a crucial role in the development of pharmaceuticals targeting fungal infections and understanding the mechanisms of toxicity associated with ochratoxins.
Used in Chemical Research:
1-Oxo-3-methyl-8-hydroxy-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid is utilized as a key compound in chemical research, particularly in the study of natural products and their biosynthetic pathways. Its unique structure makes it an interesting target for the development of new drugs and bioactive molecules with potential applications in various therapeutic areas.
Used in Agricultural Industry:
As an intermediate in the biosynthesis of Ochratoxin B, 1-Oxo-3-methyl-8-hydroxy-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid is relevant to the agricultural industry for understanding and managing the risks associated with mycotoxin contamination in crops. This knowledge can contribute to the development of strategies to prevent or reduce the presence of these toxic compounds in the food chain.

Upstream product

• 98360-99-7 N,N-diethyl-2-methoxy-3-(diethylcarbamoyl)benzamide 
• 141207-16-1 dimethyl 2-hydroxy-4-propenyl-1,3-benzenedicarboxylate 
• 98360-97-5 N,N-diethyl-2-methoxy-3-carboxybenzamide 
• 82819-70-3 O-(2-N,N-diethylcarbamoyl)phenyl N,N-diethylcarbamate 
• 65009-00-9 O-phenyl N,N-diethylcarbamate 
• 216967-83-8 N,N-diethyl-2-methoxy-3-(diethylcarbamoyl)-6-methylbenzamide 
• 1951-38-8 2-methoxyisophthalic acid 
• 98361-03-6 N,N-diethyl-2-methoxy-3-carboxy-6-allylbenzamide 
• 98361-01-4 N,N-diethyl-2-methoxy-3-(diethylcarbamoyl)-6-allylbenzamide 
• 141207-15-0 (+/-)-dimethyl 4-(2-acetoxypropyl)-2-hydroxy-1,3-benzenedicarboxylate 
• 141207-17-2 2-hydroxy-4-propenyl-1,3-benzenedicarboxylic acid 
• 83769-04-4 methyl 8-hydroxy-3-methyl-1-oxo-3,4-dihydro-(1H)-2-benzopyran-7-carboxylate 

Downstream Products

• 216967-81-6 ochratoxin B methyl ester 

Relevant academic research and scientific papers

COMPOUNDS AND COMPOSITIONS USEFUL IN THE TREATMENT OF NEOPLASIA

There is described compounds for use in therapy, said compounds being defined by Formula (1): There is also described an anti-proliferative composition comprising one or more compounds according to Formula (1), and a method of treatment of neoplasia comprising the administration of such a compound or composition.

On the role of copper and iron in DNA cleavage by ochratoxin A. Structure-activity relationships in metal binding and copper-mediated DNA cleavage

Ochratoxin A (OTA, 1: X = Cl) is a fungal carcinogen that facilitates single-strand DNA cleavage and DNA adduction when metabolically activated. To determine if redox-active transition metals induce OTA-mediated DNA damage, we have examined the toxin's ab

SYNTHESES OF (+)- AND (-)-MELLEIN UTILIZING AN ANNELATION REACTION OF ISOXAZOLES WITH DIMETHYL 3-OXOGLUTARATE

Naturally occurring dihydroisocoumarins, (+)- and (-)-mellein (2 and 3), metabolites of fungals, Cercospora sp. and Aspergillus sp., etc., were synthesized from the isoxazoles (32) and (33) by the annelation reactions with dimethyl 3-oxoglutarate.

Mise au point. Reaction de metallation ortho dirigee des composes aromatiques. Nouvelles methodologies et applications en synthese organique

In recent years, the aromatic directed metalation reaction has developed into a broadly useful protocol for the regiospecific construction of polysubstituted aromatics and has been applied in efficient total syntheses of diverse classes of natural products.In this review, both methodological and total synthesis advences using primarily the tertiary carboxamide and carbamate as metalation directors are presented.First, general aspects such as the nature of the directed metalation group (DMG) (scheme 1), the effect of two meta-related DMGs on the metalation process (scheme 2), the relative directed metalation abilities of different DMGs (scheme 3), and the scope of reaction with various electrophiles (scheme 4) are first discussed.Next, the advantage of the directed metalation tactic for the synthesis of several classes of natural products (anthramycin, scheme 7 ; angular anthracyclinones, scheme 8 ; and cannabifuran, schemes 10 and 11) are conceptualized and briefly described.Further, the significance of silicon functionality in context of directed metalation chemistry is demonstrated by its use for protection of prefferentially reactive aromatic C-H and C-methyl sites (scheme 12), ipso desilylation (scheme 13), generation of o-quinodimethanes (scheme 14), and overcoming normal Friedel-Crafts regioselectivity in carboannelation (schemes 16-18).Aspects of the tertiary carbamate as a ortho metalation director (scheme 19) are delineated : the development of an anionic ortho-Fries rearrangement (scheme 21) ; a new, also anionic, ortho-tolyl carbamate rearrangement leading to benzofuranones (scheme 22) ; its comparison with tertiary amide a methoxymethoxy as a DMG (scheme 23) ; its use for the generation of benzamide benzyne intermediates (scheme 24) ; metalation of O-pyridyl carbamates (scheme 25) and its synthetic ramifications (schemes 26-28) ; and its application in conjunction with amide metalation for the synthesis of the ochratoxin metaolites (scheme 29).Dimetalation of benzamides (scheme 32), phthalamides (scheme 33), p,p- and o,o-aryl dicarbamates (schemes 34 and 35) are supported by reactions with various electrophiles.To conclude, recent work aimed at connecting the aromatic directed metalation strategy to other modern synthetic methods is described.Coupling the directed metalation process with the radical-induced annelation provides new routes to benzofurans (scheme 36) and furopyridines (scheme 37) and is applied to the preparation of a key synthon for the mould metabolite, aflatoxin (scheme 38).Anionic aromatic and heteroaromatic ring annelation processes which depend upon ortho metalated precursors lead to naphthalene (schemes 39-41) and 4-quinolone (scheme 42) derivatives.Aryl boronic acids with ortho-DMGs, synthesized by metalation-boronation and ipso borodesilylation methods, are cross coupled with aryl bromides under palladium (O) catalysis leading to new routes for the preparation of unsymmetrical biaryls (scheme 45).