Oxolinic acid

5,8 - dihydro-5 - ethyl -8 - oxo- 1,3 - dioxolo [4,5 - g] quinoline- 7-carboxylic acid

Attention

• 525 mg · kg -1 ( LD50, rat, oral)

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Oxolinic acid is a gyrase inhibitor ( topoisomerase II inhibitor) from the family of quinolones.

Production and representation

Oxolinic acid can be obtained by a multi-step reaction starting from catechol. This reacts with formaldehyde to methylenedioxybenzene, which further reacts with nitric acid, hydrogen and diethyl ethoxymethylenemalonate. Thermal decomposition and reaction with sodium hydroxide and ethyl iodide now created the finished product.

Alternatively, oxolinic acid are obtained starting from 1,2 - methylenedioxybenzene. This is nitrated to 3,4- methylenedioxy -1 -nitrobenzene, which is hydrogenated to 3,4- methylenedioxyaniline. This then reacts with the substitution Ethoxymethylenmalonat product which. By heating to the ethyl ester of 4-hydroxy -6 ,7- methylendioxychinolin - 3-carboxylic acid is cyclized Hydrolysis with a base in dimethyl formamide and reaction with iodoethane now leads to the final product.

Use

Oxolinic acid is an antibiotic and is used as a bactericide ( Starner ) in rice cultivation. It is also effective against fire blight.