5995-97-1

Upstream product

• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 108-24-7 acetic anhydride 
• 152-95-4 sophoricoside 

Downstream Products

• 100409-92-5 5-O-methylgenistein diacetate 
• 23050-36-4 4-(5-acetoxy-7-hydroxy-4-oxo-4H-chromen-3-yl)phenyl acetate 
• 1610737-96-6 5-(benzyloxy)-3-(4-(benzyloxy)phenyl)-7-morpholino-4H-chromen-4-one 
• 1610737-92-2 5-(benzyloxy)-3-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-7-yl-4-methylbenzenesulfonate 
• 251985-66-7 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl-4-methylbenzenesulfonate 
• 1610737-86-4 4-(5-acetoxy-4-oxo-7-(tosyloxy)-4H-chromen-3-yl)phenyl acetate 
• 1610737-81-9 4-(5-acetoxy-7-(tert-butoxy)-4-oxo-4H-chromen-3-yl)phenyl acetate 
• 1610737-53-5 4-(5-acetoxy-7-((4-fluorobenzyl)oxy)-4-oxo-4H-chromen-3-yl)phenyl acetate 
• 1610737-75-1 5-hydroxy-3-(4-hydroxyphenyl)-7-morpholino-4H-chromen-4-one 
• 1610737-64-8 7-(tert-butoxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one 
• 1093389-85-5 7-((4-fluorobenzyl)oxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one 
• 4569-98-6 7-hydroxy-3-(4-hydroxy-phenyl)-5-methoxy-chromen-4-one 

Relevant academic research and scientific papers

Phosphoramidate protides of five flavones and their antiproliferative activity against HepG2 and L-O2 cell lines

A series of flavone-7-phosphoramidate derivatives were synthesized and tested for their antiproliferative activity in vitro against human hepatoma cell line HepG2 and human normal hepatic cell line L-O2. Compound 8d, 16d and 17d, incorporating the amino acid alanine, exhibited high inhibitory activity on HepG2 cell line with IC50 values of 9.0 μmol/L, 5.5 μmol/L and 6.6 μmol/L. The introduction of acyl groups played a pivotal role in the selective inhibition toward human hepatoma HepG2 cells, except for compound 8a, 9a and 16b. Compound 8d, 16d and 17d could significantly induce G2/M arrest in HepG2 cells. Specially, Compound 16d could lead early apoptosis in HepG2 cells.

Design and discovery of flavonoid-based HIV-1 integrase inhibitors targeting both the active site and the interaction with LEDGF/p75

HIV integrase (IN) is an essential enzyme for the viral replication. Currently, three IN inhibitors have been approved for treating HIV-1 infection. All three drugs selectively inhibit the strand transfer reaction by chelating a divalent metal ion in the

An efficient method for the glycosylation of isoflavones

The isoflavone phytoestrogens are still of current interest for their positive and negative health benefits. However, there are still many unanswered questions regarding their absorption, metabolism and bioavailability. Studies in this area require access to samples of both the isoflavone 7-O-glucosides, the form found in plants and the 7-O-glucuronides, which are important mammaliam metabolites. A new efficient, high-yielding glycosylation procedure is described for isoflavones, which employs 2,2,2-trifluoro-N-(p-methoxyphenyl) acetamidates as the glycosyl donors. This methodology was used to prepare the 7-O-glycosides of the three main isoflavones, daidzein, genistein and glycitein. The isoflavones were protected with hexanoyl groups which improved their solubility in organic solvents and improved the efficiency of the reaction. The same methodology was then adapted for the synthesis of the analogous 7-O-glucuronides. The new synthesis will provide access to large quantities of these compounds for further biological studies. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Dietary phytoestrogens and their synthetic structural analogues as calcium channel blockers in human platelets.

Phytoestrogens have been shown to inhibit platelet activation by blocking platelet calcium channels. This study examined the effect of several synthetic derivatives of trans-resveratrol, genistein, and daidzein on platelet free intracellular calcium ([Ca2+]i) elevation in thrombin-activated platelets and the possible mechanisms of this inhibitory effect. Studies were conducted on fresh human platelets from healthy volunteers. The fluorescent dye fura-2 was used to monitor [Ca2+]i in platelets. At 10 microM-resveratrol, triacetyl-trans-resveratrol, and trimethoxy-trans-resveratrol produced, respectively, 57 +/- 4%, 40 +/- 4%, and 21 +/- 1% inhibition; genistein, acetylgenistein, and dihydrogenistein produced 51 +/- 10%, 26 +/- 7%, and 16 +/- 2% inhibition, respectively; daidzein and diacetyldaidzein produced 56 +/- 5% and 45 +/- 10% inhibition of thrombin-induced [Ca2+]i elevation. The inhibitory effect was immediate and appeared to directly affect the calcium influx channels. Phytoestrogen action on [Ca2+]i did not cause alteration in nitric oxide signaling. Tyrosine phosphorylation was not involved in the inhibition of [Ca2+]i elevation by phytoestrogens, because the percent inhibition produced by the tyrosine kinase inhibitor genistein and its inactive analogue daidzein on thrombin-induced and thapsigargin-induced [Ca2+]i elevation was not significantly different for either compound at any concentration tested. Structure-activity relationship studies on this limited set of compounds reveal the requirements for the stilbene pharmacophore for the calcium-blocking activity.

Study of sophoricoside derivatives with the aid of lanthanoid shift reagents

Acylated and methylated derivatives of sophoricoside and of genistein have been synthesized, and their interaction in solution with the lanthanoid shift reagent (LSR) Eu(FOD)3 has been studied. For 5-O-alkyl derivatives of genistein an anomalous broadening of the 1H NMR signals was observed in the presence of the LSR, which is explained by the formation with the LSR of a chelate having a low rate of dissociation. The temperature and concentration dependencies of the paramagnetic broadenings of the signals have been studied.