Indol-3-ylacetic acid

The diketoindoles 777 were prepared in three steps starting from indol-3-ylacetic acid (680) and 5-chloro indol-3-ylacetic acid (774) in 75% and 66% overall yield, respectively. The indole acids 680 and 774 were converted into Weinreb amides 775, followed by reaction with ethyl Grignard reagent to afford the corresponding indol-3-yl ketones 776. In order to introduce the second carbonyl moiety, the 3-substituted... 

The mechanism of metabolic degradation of indol-3-ylacetic acid (39) is a matter of debate. A possible route demonstrated in vitro includes oxidative decarboxylation to skatolyl hydroperoxide (40), catalyzed by horseradish peroxidase isoenzyme C (HRP-C), followed by rearrangement to 3-(hydroxymethyl)oxindole (41), as shown in equation 12 . 

The MS of compound 40, a putative intermediate of the metabolic degradation of indol-3-ylacetic acid (39), shows the molecular peak at m e 163 and the parent negative peak at 162. This and other spectral and chemical evidence pointed to the compound being a hydroperoxide . 

To make use of the Mannich reaction it is possible to methylate the N-atom of the new side chain and eliminate trimethylamine. The product, a 3-methyleneindoleninium salt, can then be trapped with suitable nucleophiles. In the example shown in Scheme 7.7b, cyanide ion is used, and reduction of the resultant nitrile yields the important amine trypta-mine. Indol-3-ylacetonitrile is also the source of indol-3-ylacetic acid and other biologically useful compounds (see Section 7.1.7). 

Both compounds are rapidly translocated herbicides that selectively kill broad-leaved weeds. They mimic the natural auxin, indol-3-ylacetic acid, which is responsible for promoting cell elongation and hence cause unrestrained growth. This uses up all the available nutrients, leading to the death of the plant. A review of the pyridinecarboxylic acids has been published (B-75MI10702). 

Iminoctadine guanidine Inabenfide amide, pyridine Indol-3-ylacetic acid heterocyclic nitrogen, indole 4-Indol-3-ylbutyric acid heterocyclic nitrogen, indole... 

Glycine cypermethrin, eglinazine, glyphosate, 8-hydroxy quinoline sulfate, iprodione, proglinazine Glycoaldehyde fenfuram Glycolide indol-3 ylacetic acid Glyoxylic acid oxamyl... 

Disposition in the Body. It is inactive when taken orally. After intramuscular injection it is rapidly and extensively metabolised, primarily to indol-3-ylacetic acid. About 33% of a dose is excreted in the urine in 6 hours as free and conjugated... 

Acetylation of indol-3-ylacetic acid leads, in situ, to an enol-lactone an indole fnsed to a 2-pyrone. This can be hydrolysed to the keto-acid, or the diene character of the 2-pyrone (11.2.2.4) can be utilised, as illustrated. ... 

Starting from indole, and using a common intermediate, how could one prepare (i) indol-3-ylacetic acid and (ii) tryptamine ... 

The physiological activity of lysergic acid diethylamide (LSD) is notorious. The synthetic indol-3-ylacetic acid derivative Indomethacin is used for the treatment of rheumatoid arthritis. 

The growth of plants can be retarded by inhibiting the transport of the auxin, indol-3-ylacetic acid. Schneider (1964) prepared a series offluorene derivatives to produce dwarf varieties of economic plants. Another use of these morph-actins, as they are called, is to retard the growth of dicotyledonous weeds in a... 

Price-Jones, M.J. and Harwood, J. L. (1983) Hormonal regulation of phosphatidylcholine synthesis in plants. The inhibition of cytidylyltransferase activity by indol-3-ylacetic acid, Biochem. J. 216, 627-631. 

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