4537-34-2

Upstream product

• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 121-33-5 vanillin 
• 100-44-7 benzyl chloride 
• 32865-61-5 2-iodophenyl acetate 
• 261785-34-6 3-(o-acetoxyphenyl)-1-(m-methoxy-p-benzyloxyphenyl)prop-2-yn-ol 
• 27320-50-9 1-(3'-Methoxy-4'-benzyloxyphenyl)prop-2-ynol 

Downstream Products

• 1209470-01-8 4'-hydroxy-3'-methoxy-5'-benzylflavanone 
• 112818-98-1 4'-benzyloxy-3'-methoxyflavonol 
• 159184-95-9 3-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

3′-Hydroxy-3,4′-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells

Flavonoids are naturally occurring polyphenolic compounds and are among the most promising anticancer agents. A series of flavonols and their 3-methyl ether derivatives were synthesized and assessed for cytotoxicity. It was found that 3′-hydroxy-3,4′-dime

Exploration of Pharmacophore in Chrysosplenol C as Activator in Ventricular Myocyte Contraction

Chrysosplenol C (4',5,6-trihydroxy-3,3',7-trimethoxyflavone) isolated from Miliusa balansae has unique structural features as a reversible inotropic agent independent of β-adrenergic signaling and with selective activation of cardiac myosin ATPase. Hence, a series of chrysosplenol analogues were synthesized and explored for identification of pharmacophore that is essential for the increasing contractility in rat ventricular myocytes. Analogue 7-chloro-2-(3-hydroxyphenyl)-3-methoxy-4H-chromen-4-one showed highly potent contractility (54.8% at 10 μM) through activating cardiac myosin ATPase (38.7% at 10 μM). Our systematic structure-activity relationship study revealed that flavonoid nucleus of chrososplenol C appears to be an essential basic skeleton and hydrophobic substituent at position 7 of chromenone such as methoxy or chloro enhances the activity. Additionally, our ATPase study suggested that these chrysosplenol analogues have selectivity toward cardiac myosin activation. Thus, the novel flavonone with 3-/7-hydrophobic substituent and 3'-hydrogen bonding donor function is a novel scaffold for discovery of a new positive inotropic agent.

Synthesis of dihydrodehydrodiconiferyl alcohol: The revised structure of lawsonicin

Structural revision of lawsonicin, a natural product of Lawsonia alba, is reported based upon comparison of its spectral data with that of the naturally occurring dihydrobenzo[b]furan neolignan (rac)-trans-dihydrodehydrodiconiferyl alcohol, which is found to be identical. A concise synthesis of dihydrodehydrodiconiferyl alcohol, via Rh2[S-DOSP]4-catalysed intramolecular C-H insertion, is described. 10.1039/b918179b The Royal Society of Chemistry 2010.

Acidic rearrangement of (benzyloxy)chalcones: A short synthesis of chamanetin

Treatment of (benzyloxy)chalcones with trifluoroacetic acid in refluxing chloroform gave several new benzyl(hydroxy)flavanones in high yields and good regioselectivities. By using this procedure, we prepared the natural compound chamanetin in good yield from readily available reagents. Georg Thieme Verlag Stuttgart - New York.

Synthesis of a library of glycosylated flavonols

Flavonols are an important class of natural products isolated from plants. Some glycosylated flavonols showed very interesting biological activities. A library of flavonols has been made through Algar-Flynn-Oyamada reaction from 2′-hydroxyacetophenones an

Understanding the cardioprotective effects of flavonols: Discovery of relaxant flavonols without antioxidant activity

3′,4′-Dihydroxyflavonol (DiOHF) is a cardioprotective flavonol that can reduce injury after myocardial ischemia and reperfusion and thus is a promising small molecule for the treatment of cardiovascular disease. Like all vasoactive flavonols reported to date, DiOHF is both relaxant and antioxidant, hindering investigation of the relative contribution of each activity for the prevention of reperfusion injury. This study investigates structure-activity relationships of variations at the 3′ and 4′ positions of the B ring of DiOHF and vasorelaxant and antioxidant activities. Relaxation of rat isolated aortic rings precontracted with KCl revealed that the most active flavonols were those with a 4′-hydroxyl group, with the opening of potassium channels as a possible contributing mechanism. For the antioxidant activity, with the exception of DiOHF, none of the flavonols investigated were able to significantly scavenge superoxide radical, and none of the three most potent vasorelaxant flavonols could prevent oxidant-induced endothelial dysfunction. The discovery of single-acting vasorelaxant flavonols without antioxidant activity, in particular 4′-hydroxy-3′-methoxyflavonol, will assist in investigating the mechanism of flavonol-induced cardioprotection.

Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure-activity relationships

A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-positive), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compounds resulted very active against at least two of the studied tumoral cells. Alkaline single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compounds on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship analysis of these compounds was performed and for 4- and 3,4-disubstituted derivatives a quantitative correlation was obtained in the case of anti-HT-29 activity.

A concerted synthesis of hydroxychalcones, flavanones and benzo[b]furans through palladium-catalysed reactions

A convenient palladium-catalysed procedure for the synthesis of o-hydroxychalcones, flavanones and benzo[b]furans is described where o-iodophenyl acetate was used as a common precursor.