136944-33-7Relevant academic research and scientific papers
Nucleophilic deoxyfluorination of catechols
Nemoto, Hiroyuki,Nishiyama, Tsuyoshi,Akai, Shuji
, p. 2714 - 2717 (2011/06/28)
Nucleophilic deoxyfluorinaiton of one of the two hydroxyl groups of catechols has been developed via the Umpolung concept. This method was successively applied to naturally occurring catechols, such as catechins and dopamine, to produce novel fluorinated
Quantitative structure-activity relationship of catechol derivatives inhibiting 5-lipoxygenase
Naito,Sugiura,Yamaura,Fukaya,Yokoyama,Nakagawa,Ikeda,Senda,Fujita
, p. 1736 - 1745 (2007/10/02)
Various catechol derivatives (β-substituted 3,4-dihydroxystyrenes, 1-substituted 3,4-dihydroxybenzenes, and 6-substituted 2,3-dihydroxynaphthalenes) were synthesized and their inhibition of 5-lipoxygenase was assayed. Their structure-activity relationships were examined quantitatively with substituent and structural parameters and regression analysis. The variations in the inhibitory activity were explained in bilinear hydrophobic parameter (log P) terms, and steric (molecular thickness) and electronic (proton nuclear magnetic resonance (1H-NMR) chemical shift of the proton adjacent to the catechol group) parameter terms. The hydrophobicity of the inhibitor molecule was important, and the optimum value of log P was about 4.3-4.6, beyond which inhibition did not increase further. A low electron density of the aromatic ring containing the catechol group and the greater thickness of the lipophilic side chains were unfavorable to the activity. The results added a physicochemical basis for the selection of candidate compounds for developmental studies.
