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

Autori
Nigović, Biljana ; Antolić, Snježana ; Kojić-Prodić, Biserka ; Kiralj, Rudolf ; Magnus, Volker ; Salopek-Sondi, Branka

Izvornik
Acta crystallographica. Section B, Structural science (0108-7681) 56 (2000), 1; 94-111

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Indole-3-acetic acid ; Phytohormone ; Bioactivity ; Molecular recognition studies.

Sažetak
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 (alkyl = methyl and ethyl) at positions 4-, 6-, or 7- as well as pyrrole substitution at the site 2- resulted in the six compounds which are 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, the 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 van der Waals radii of the ring-substituents. The influence of substitution on the electronic properties of the indole ring and its geometry is discussed on the basis of the UV and H-1 NMR spectra. _____________________________________

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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