84161-84-2Relevant articles and documents
Development of a novel nitric oxide (NO) production inhibitor with potential therapeutic effect on chronic inflammation
Chen, Lijuan,Fan, Tiantian,Lei, Xiangui,Teichmann, Alexander Tobias,Wang, Amu,Wang, Chao,Wei, Zhe,Wieland, Frank Heinrich,Yang, Youzhe,Yin, Jinxiang,Zhou, Li,Zhu, Yue
, (2020/03/24)
Inflammation is a complex biological response to stimuli. Activated macrophages induced excessively release of pro-inflammatory cytokines and mediators such as endogenous radical nitric oxide (NO) play a significant role in the progression of multiple inflammatory diseases. Both natural and synthetic chalcones possess a wide range of bioactivities. In this work, thirty-nine chalcones and three related compounds, including several novel ones, based on bioactive kava chalcones were designed, synthesized and their inhibitory effects on NO production in RAW 264.7 cells were evaluated. The novel compound (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3-methoxy-4-(3-morpholinopropoxy)phenyl)prop-2-en-1-one (53) exhibited a better inhibitory activity (84.0%) on NO production at 10 μM (IC50 = 6.4 μM) with the lowest cytotoxicity (IC50 > 80 μM) among the tested compounds. Besides, western blot analysis indicated that compound 53 was a potent down-regulator of inducible nitric oxide synthase (iNOS) protein. Docking study revealed that compound 53 also can dock into the active site of iNOS. Furthermore, at the dose of 10 mg/kg/day, compound 53 could both significantly suppress the progression of inflammation on collagen-induced arthritis (CIA) and adjuvant-induced arthritis (AIA) models. In addition, the structure-activity relationship (SAR) of the kava chalcones based analogs was also depicted.
Antimitotic and antiproliferative activities of chalcones: Forward structure-activity relationship
Boumendjel, Ahcène,Boccard, Julien,Carrupt, Pierre-Alain,Nicolle, Edwige,Blanc, Madeleine,Geze, Annabelle,Choisnard, Luc,Wouessidjewe, Denis,Matera, Eva-Laure,Dumontet, Charles
, p. 2307 - 2310 (2008/12/22)
A series of 59 chalcones was prepared and evaluated for the antimitotic effect against K562 leukemia cells. The most active chalcones were evaluated for their antiproliferative activity against a panel of 11 human and murine cell cancer lines. We found that three chalcones were of great interest as potential antimitotic drugs. In vivo safety studies conducted on one of the most active chalcones revealed that the compound was safe, allowing further in vivo antitumor evaluation.
Synthesis of isoflavones containing naturally occurring substitution pattern by oxidative rearrangement of respective flavanones using thallium(III) p-tosylate
Singh, Om V.,Muthukrishnan,Sunderavadivelu
, p. 2575 - 2581 (2007/10/03)
Claisen condensation of substituted 2′-hydroxyacetophenones 1a-c with aromatic aldehydes affords respective substituted 2′-hydroxychalcones 2a-n which on base catalyzed cyclization in pyridine:methanol:water (1:1:1) give respective flavanones 3a-n. The oxidative rearrangement of flavanones with thallium(III) p-tosylate furnishes respective isoflavones 4a-n in overall 62-72% yields starting from 1. The present methodology has been successfully applied for the synthesis of naturally occurring isoflavones such as di-O-methyldaidzein 4a, cabruvin 4b, pseudobabtigenin methylether 4d, 5,7-dimethoxyisoflavone 4f, 5,7,4′-trimethoxyisoflavone 4g, derrustone 4i, 7,8,3′,4′- tetramethoxyisoflavone 41, purpuranin-A 4m and 7,8,3′,4′,5′- pentamethoxyisoflavone 4n and thus the first synthesis of 4n is reported.
