engleski

Correlation of structural and physico-chemical parameters with the bioactivity of alkylated derivatives of indole-3-acetic acid, a phytohormone (auxin)

As part of molecular recognition studies on the phytohormone, indole-3-acetic acid (IAA), a series of alkylated IAAs has been examined. Phenyl-ring substitution at positions 4-, 6-, or 7- as well as pyrrole substitution at the site 2 resulted in the six compounds which were analyzed: 2-Me-IAA, 4-Me-IAA, 6-Me-IAA, 7-Me-IAA, 4-Et-IAA, and 6-Et-IAA. Structure-activity relationship includes the geometrical parameters of the molecular structures determined by X-ray analysis, electronic properties defined on the base of the UV and H-1 NMR spectra, growth-promoting activities in the Avena coleoptile straight-growth bioassay, and relative lipophilicities calculated from retention times on a reversed-phase HPLC column and from RF-values in reversed-phase TLC. Lipophilicities are correlated with the momenta of inertia, average polarizability, molecular mass, and the volume of the ring-substituent.

phytohormone; auxin; ring-substituted indole-3-acetic acid; structure activity correlation; molecular recognition

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