927429-56-9Relevant academic research and scientific papers
Divergent approach to flavones and aurones via dihaloacrylic acids. unexpected dependence on the halogen atom
Kraus, George A.,Gupta, Vinayak
supporting information; experimental part, p. 5278 - 5280 (2011/02/21)
The reaction of phenols with 7a led to the synthesis of aurones, while the reaction of phenols with 7b led to the synthesis of flavones.
Synthesis and insect antifeedant activity of aurones against spodoptera litura larvae
Morimoto, Masanori,Fukumoto, Hiromi,Nozoe, Toki,Hagiwara, Ai,Komai, Koichiro
experimental part, p. 700 - 705 (2009/10/01)
A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect antifeedant activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 μmol/cm2. The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect antifeedant activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect antifeedant activity, but 4,5,6- and 3 ,4 ,5 -trisubstituted compounds did not show this activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect antifeedant activity against S. litura. Although the melting points did not correlate well with the insect antifeedant activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological activity (pED50) and a hydrogen-bonding parameter calculated from the Rf value obtained from SiOH thin-layer chromatography and a lipophilicity parameter (log k) calculated from the retention time in ODS high-performance liquid chromatography. The respective correlation coefficients (r) were -0.83 and -0.70. The introduction of alkoxy and alkyl groups along with adequate hydrogen bonding seems to contribute to the antifeedant activity of the compounds tested.
