26964-24-9Relevant articles and documents
Insect antifeedant activity of flavones and chromones against Spodoptera litura
Morimoto, Masanori,Tanimoto, Kumiko,Nakano, Sachiko,Ozaki, Takayoshi,Nakano, Ayako,Komai, Koichiro
, p. 389 - 393 (2003)
The antifeedant polymethylated flavones 5-hydroxy-3,6,7,8,4′-heptamethoxyflavone, 5-hydroxy-3,6,7,8-tetramethoxyflavone, and 5,6-dihydroxy-3,7-dimethoxyflavone have been isolated from the cudweed, Gnaphalium affine D. Don (Compositae). These flavonoids and authentic analogues showed insect antifeedant activity against the common cutworm (Spodoptera litura F.). In a previous paper, it was suggested that there was no substituent on the B-ring of the flavonoid for the beneficial antifeedant activity against the common cutworm. These flavonoids having a phenyl group as the B-ring and the chromone as elimination of the B-ring from the flavonoids were used to test the hypothesis of the previously described B-ring effect. The known fact is that Sculletaria baicarensis (Rutaceae) produced the 2-phenyl flavone. Test compounds and their methylated derivatives were prepared from this material for the structure-activity relationship (SAR) study of insect antifeedant activity. In spite of the 2-phenyl flavonoids, some tested compounds did not show any insect antifeedant activity against the common cutworm, although these inactive flavonoids were deficient in the 6-substituent group on the A-ring of the flavonoid. This 6-position-substituted derivative almost showed strong insect antifeedant activity against common cutworm. Moreover, the tested flavonoids having a hydroxyl group as a substituent on any of the positions tended to increase the activity. These results suggested the importance of the 6-position substitution on the flavonoid; however, hydrophilic substituents decreased the activity. Baicalein (5,6,7-trihydroxyflavone) derivatives did not show any activity despite having the 6-substituent derivative. Although the activity of some chromones increased the activity of the flavone, the bulky B-ring was a disadvantage for the antifeedant activity. It was suggested that the charge on C(3) and C(5) of the flavonoid was important for the biological activity. Additionally, an adequate hydrogen bonding property, which is different from lipophilicity, was an advantage for the activity on the basis of a QSAR analysis.
Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization
Son, Seung Hwan,Cho, Yang Yil,Yoo, Hyung-Seok,Lee, Soo Jin,Kim, Young Min,Jang, Hyu Jeong,Kim, Dong Hwan,Shin, Jeong-Won,Kim, Nam-Jung
, p. 14000 - 14006 (2021/04/22)
Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.
Discovery of polymethoxyflavones as potential cyclooxygenase-2 (COX-2), 5-lipoxygenase (5-LOX) and phosphodiesterase 4B (PDE4B) inhibitors
Hamzah, Ahmad Sazali,Md Idris, Muhd Hanis,Mohd Amin, Siti Norhidayah,Mohd Amin, Siti Norhidayu,Salleh, Mohd Zaki,Selvaraj, Manikandan,Shaameri, Zurina,Teh, Lay Kek,Wibowo, Agustono,Zakaria, Zainul Amiruddin
, (2021/08/06)
Non-steroidal anti-inflammatory drugs (NSAIDs) are widely prescribed to treat inflammatory-related diseases, pain and fever. However, the prolong use of traditional NSAIDs leads to undesirable side effects such as gastric, ulceration, and renal toxicity due to lack of selectivity toward respective targets for COX-2, 5-LOX, and PDE4B. Thus, targeting multiple sites can reduce these adverse effects of the drugs and increase its potency. A series of methoxyflavones (F1–F5) were synthesized and investigated for their anti-inflammatory properties through molecular docking and inhibition assays. Among these flavones, only F2 exhibited selectivity toward COX-2 (Selectivity Index, SI: 3.90, COX-2 inhibition: 98.96 ± 1.47%) in comparison with celecoxib (SI: 7.54, COX-2 inhibition: 98.20 ± 2.55%). For PDEs, F3 possessed better selectivity to PDE4B (SI: 4.67) than rolipram (SI: 0.78). F5 had the best 5-LOX inhibitory activity among the flavones (33.65 ± 4.74%) but less than zileuton (90.81 ± 0.19%). Docking analysis indicated that the position of methoxy group and the substitution of halogen play role in determining the bioactivities of flavones. Interestingly, F1–F5 displayed favorable pharmacokinetic profiles and acceptable range of toxicity (IC50>70 μM) in cell lines with the exception for F1 (IC50: 16.02 ± 1.165 μM). This study generated valuable insight in designing new anti-inflammatory drug based on flavone scaffold. The newly synthesized flavones can be further developed as future therapeutic agents against inflammation.
CeO2-Supported Pd(II)-on-Au Nanoparticle Catalyst for Aerobic Selective α,β-Desaturation of Carbonyl Compounds Applicable to Cyclohexanones
Jin, Xiongjie,Mizuno, Noritaka,Takei, Daisuke,Yabe, Tomohiro,Yamaguchi, Kazuya,Yatabe, Takafumi
, p. 5057 - 5063 (2020/05/27)
Direct selective desaturation of carbonyl compounds to synthesize α,β-unsaturated carbonyl compounds represents an environmentally benign alternative to classical stepwise procedures. In this study, we designed an ideal CeO2-supported Pd(II)-on-Au nanoparticle catalyst (Pd/Au/CeO2) and successfully achieved heterogeneously catalyzed selective desaturation of cyclohexanones to cyclohexenones using O2 in air as the oxidant. Besides cyclohexenones, various bioactive enones can also be synthesized from the corresponding saturated ketones under open air conditions in the presence of Pd/Au/CeO2. Preliminary mechanistic studies revealed that α-C-H bond cleavage in the substrates is the turnover-limiting step of this desaturation reaction.
