15485-66-2Relevant articles and documents
Syntheses, characterization and antitumor activities of transition metal complexes with isoflavone
Chen, Xiang,Tang, Li-Jun,Sun, Yu-Na,Qiu, Pei-Hong,Liang, Guang
, p. 379 - 384 (2010)
Five new complexes were synthesized by the reaction of 4′-methoxy-5,7-dihydroxy-isoflavone ligand (a) with transition metal ions zinc (Zn2+) (complex b), manganese (Mn2+) (complex c), copper (Cu2+) (complex d), cobalt (Co2+) (complex e) and nickel (Ni2+) (complex f). The composition of the complexes has been characterized by elemental analysis, IR, mass spectrometry (MS) and 1H NMR spectrometric techniques. Their antitumor properties were evaluated against five human cancer cell lines using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and flow cytometry. The results indicated that the complexes possess higher growth inhibitory effects than free isoflavone and corresponding metal ions. Complex c and f showed greater antitumor activity and selectivity than other described complexes, even more effective than the positive control cisplatin against the selected cell lines. In addition, DNA flow cytometric analysis demonstrated that complexes display a significant G2/M phase arrest, which then progressed to early apoptosis as detected by flow cytometry after double-staining with annexin V and propidium iodide (PI).
A Direct Synthesis of 2-(ω-Carboxyalkyl)isoflavones from ortho-Hydroxylated Deoxybenzoins
Mrug, Galyna P.,Demydchuk, Bohdan A.,Bondarenko, Svitlana P.,Sviripa, Vitaliy M.,Wyrebek, Przemyslaw,Mohler, James L.,Fiandalo, Michael V.,Liu, Chunming,Frasinyuk, Mykhaylo S.,Watt, David S.
supporting information, p. 5460 - 5463 (2018/10/20)
As part of a program focused on the development of new antineoplastic agents based on scaffolds found in natural products, we explored the isoflavone family as potential enzyme inhibitors. We required biotin-modified isoflavones to identify potential biological targets, and we selected the C-2 position in isoflavones as an attachment site for an alkyl group bearing a terminal carboxylic acid to which we could attach a biotin derivative. The base-catalyzed condensation of 2,4-dihydroxy-substituted deoxybenzoins with cyclic anhydrides mediated by a combination of triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene led to an efficient synthesis of the desired 2-(ω-carboxyalkyl)isoflavones with functional groups at C-5, 6 and 7 and with various substituents in the C-3 phenyl group.
Synthesis method of biochanin A
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Paragraph 0035; 0036, (2017/08/23)
The invention provides a synthesis method of biochanin A. The synthesis method includes: under room temperature, adding phosphorus oxychloride into phloroglucinol, 4-Methoxybenzyl cyanide and isopropyl ether, performing hydrolysis after reaction is completed, and decoloring with activated carbon to obtain an intermediate; allowing the obtained intermediate and methylsufonyl chloride to generate crude products of the biochanin A in DMF (dimethyl formamide) in a ring-closing manner; performing recrystallization on the obtained crude products of the biochanin A by adopting ethyl alcohol and decoloring with the activated carbon to obtain the biochanin A. The synthesis method is simple in process, low in cost, timesaving, high in yield, low in equipment corrosiveness and suitable for industrialized production.
Ester and carbamate ester derivatives of Biochanin A: Synthesis and in vitro evaluation of estrogenic and antiproliferative activities
Fokialakis, Nikolas,Alexi, Xanthippi,Aligiannis, Nektarios,Siriani, Despina,Meligova, Aggeliki K.,Pratsinis, Harris,Mitakou, Sofia,Alexis, Michael N.
experimental part, p. 2962 - 2970 (2012/07/16)
Biochanin A (BCA), a major isoflavone in red clover and many other legumes, has been reported to display estrogenic as well as cancer chemopreventive properties. Ingested BCA is known to display low bioavailability due to poor solubility, extensive metabolism and rapid clearance. Esters of bioactive isoflavones are known to increase metabolic stability and bioavailability following local rather than systemic administration. We synthesized BCA from phloroglucinol and p-methoxy-phenylacetic acid by a Friedel-Crafts reaction and cyclization. We also synthesized esters (1, 3) and carbamate esters (2, 4, 5) at position 7 of BCA using short aliphatic chains bearing a chlorine (1, 2) or a bromine atom (3, 4) or long aliphatic chains without such atoms (5). We tested the estrogenic and antiproliferative activities of 1-5 and BCA using human breast and endometrial adenocarcinoma cells. We found that 5 affects MCF-7 and Ishikawa cells in a manner providing for induction of gene expression to a level similar to 17β-estradiol and BCA but, unlike both of the latter, for suppression of cell proliferation as well. In addition, 5 appeared to display higher stability compared to 1-4 and BCA in both MCF-7 and Ishikawa cells. The inference is that 5 may represent a safer than BCA alternative to hormone replacement therapy.
