172805-73-1

Upstream product

• 520-34-3 diosmetin 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 1094471-10-9 7-benzyloxy-2-(3-benzyloxy-4-methoxyphenyl)-5-trifluoromethanesulfonyloxy-4H-chromen-4-one 
• 172805-74-2 7-Benzyloxy-2-(3-benzyloxy-4-methoxy-phenyl)-5-(2-hydroxy-ethoxy)-chromen-4-one 
• 172805-75-3 [7-Benzyloxy-2-(3-benzyloxy-4-methoxy-phenyl)-4-oxo-4H-chromen-5-yloxy]-acetic acid ethyl ester 

Relevant academic research and scientific papers

A convenient microwave-assisted 5-amination of flavones

A few examples of 5-aminoflavones' syntheses exist in the literature and for those, which are described, the amino group is introduced before the formation of the flavone skeleton. We describe here an efficient method, which permits the access to 5-aminoflavones by a simple procedure using an SNAr amination under microwaves irradiation.

Semisynthesis of linarin, acacetin, and 6-iodoapigenin derivatives from diosmin

Semisynthesis of linarin and acacetin from the Citrus flavonoid diosmin was performed via, as first intermediate, the 3′-O-phenyltetrazolyl ether of diosmin. This paper relates also a semisynthetic access to 6-iodoapigenin derivatives, which are key compounds in the synthesis of some biflavonoids such as robustaflavone.

Flavonoid-related modulators of multidrug resistance: Synthesis, pharmacological activity, and structure-activity relationships

A series of 28 flavonoid derivatives containing a N-benzylpiperazine chain have been synthesized and tested for their ability to modulate multidrug resistance (MDR) in vitro. At 5 μM, most compounds potentiated doxorubicin cytotoxicity on resistant K562/DOX cells. They were also able to increase the intracellular accumulation of JC-1, a fluorescent molecule recently described as a probe of P-glycoprotein-mediated MDR. This suggests that these compounds act, at least in part, by inhibiting P-glycoprotein activity. As in other studies, lipophilicity was shown to influence MDR- modulating activity but was not the only determinant. Diverse di- and trimethoxy substitutions on N-benzyl were examined and found to affect the activity differently. The most active compounds had a 2,3,4- trimethoxybenzylpiperazine chain attached to either a flavone or a flavanone moiety (13, 19, 33, and 37) and were found to be more potent than verapamil.

Synthesis of O-(β-hydroxyethyl) derivatives of diosmetin

Five O-(β-hydroxyethyl) derivatives (3, 4, 5, 6, 7) of diosmetin have been synthesized for the first time. Compounds 3 and 6 have been obtained by hydrolysis of 3'-O-(β-hydroxyethyl)- and 3′,5-di-O-(β-hydroxyethyl)diosmin, respectively. Compound 4 has been prepared from diosmetin, after protecting the hydroxyls at C-7 and C-3′, using ethylene oxide or ethyl chloroacetate and sodium borohydride, followed by removal of the protective groups. Compounds 5 and 7 have been prepared by the reaction of diosmetin (8) and 6 with ethylene chlorohydrin, respectively.