- Syntheses, characterization and antitumor activities of transition metal complexes with isoflavone
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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).
- Chen, Xiang,Tang, Li-Jun,Sun, Yu-Na,Qiu, Pei-Hong,Liang, Guang
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- A Direct Synthesis of 2-(ω-Carboxyalkyl)isoflavones from ortho-Hydroxylated Deoxybenzoins
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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.
- 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.
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supporting information
p. 5460 - 5463
(2018/10/20)
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- Synthesis, Characterization, and Antioxidant Activities of Genistein, Biochanin A, and Their Analogues
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A series of naturally occurring genistein (3) and biochanin A (4) compounds and their analogues were synthesized from phloroglucinol. The structures of all the synthesized compounds were established by the combined use of 1HNMR, 13CNMR, IR spectral data, and mass spectrometry; their antioxidant activities were investigated. Most of the synthesized compounds show moderate-to-high activity; only two compounds exhibit no significant activity.
- Hamza Sherif, Salah,Gebreyohannes, BerihuTekluu
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- Synthesis method of biochanin A
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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.
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Paragraph 0035; 0036
(2017/08/23)
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- Synthesis and aminomethylation of 7-hydroxy-5-methoxyisoflavones
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A synthetic method for 7-hydroxy-5-methoxyisoflavones starting from 5,7-dihydroxyisoflavones was developed. Dimethylcarbamoylchloride was proposed for protection of the 7-hydroxy group. Aminomethylation of the synthesized 7-hydroxy-5-methoxyisoflavones by formaldehyde aminals was studied.
- Mrug,Bondarenko,Khilya,Frasinyuk
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p. 235 - 241
(2013/07/26)
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- Ester and carbamate ester derivatives of Biochanin A: Synthesis and in vitro evaluation of estrogenic and antiproliferative activities
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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.
- Fokialakis, Nikolas,Alexi, Xanthippi,Aligiannis, Nektarios,Siriani, Despina,Meligova, Aggeliki K.,Pratsinis, Harris,Mitakou, Sofia,Alexis, Michael N.
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experimental part
p. 2962 - 2970
(2012/07/16)
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- Synthesis and structure-activity relationship study of deoxybenzoins on relaxing effects of porcine coronary artery
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Deoxybenzoins are potent antioxidants and tyrosinase inhibitors with potential to be developed as food preservatives and cosmetic ingredients. To explore the potential in cardiovascular protection, 25 polyphenolic deoxybenzoins were synthesized and evaluated for inhibitory effects on KCl-induced porcine coronary arterial contraction. The results revealed deoxybenzoins are significant inhibitors of KCl-induced arterial contraction. Among those synthesized, two-thirds of the deoxybenzoins exhibited moderate to good efficacy on relaxing contracted artery including 2,4-dihydroxydeoxybenzoin with EC50 = 3.30 μM (Emax = 100%, n = 7) and 2,4-dihydroxy-4′-methoxydeoxybenzoin EC50 = 3.70 μM (E max = 100%, n = 5). Deoxybenzoins displayed an endothelium-dependent relaxing manner on the contracted artery; the contractile responses of neither endothelium denuded nor L-NAME deactivated rings were inhibited. The structure-activity relationships of deoxybenzoin on arterial relaxing effects concluded that the 2,4-dihydroxylated deoxybenzoins presented a potential vascular relaxing pharmacophore, with favoring substitution on ring B in the order of H ≤ p-OMe > p-OH > o-OMe > m,p-diOMe ≤ m-OMe.
- Lu, Tzy-Ming,Kuo, Daih-Huang,Ko, Horng-Huey,Ng, Lean-Teik
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experimental part
p. 10027 - 10032
(2011/05/17)
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- Potential antioxidants and tyrosinase inhibitors from synthetic polyphenolic deoxybenzoins
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Deoxybenzoins (DOBs) are one-pot synthetic precursors of isoflavones with feature analogous to those beneficial polyphenols such as resveratrol (stilbene) and phloretin (dihydrochalcone). In this study, seventeen polyphenolic DOBs were synthesized and evaluated by various antioxidant assays and tyrosinase inhibitory effect in vitro. Results displayed that these DOBs are powerful antioxidants; for example, 2,3,4-trihydroxy-3′,4′-dimethoxydeoxybenzoin possesses an excellent anti-lipid peroxidation activity (IC50 = 0.72 ± 0.16 μM), whilst 2,4,4′,5-tetrahydroxydeoxybenzoin showed good DPPH radical scavenging activity (IC50 = 0.69 ± 0.04 μM), which were better than Trolox and vitamin C. Besides exhibiting a weak metal chelating effect, these DOBs were effective in scavenging ABTS{radical dot}+ and superoxide anion (O2{radical dot} -) radicals. DOBs also exhibited potent mushroom tyrosinase inhibitory activity; for example 2,3,4′-trihydroxy-4-methoxydeoxybenzoin displayed stable and significant inhibitory effect on tyrosinase activity, with IC50 values 43.37, 43.10 and 46.10 μM at incubation intervals of 0.5, 1.5, and 2.5 h, respectively. These results suggest that, with the advantage of being readily synthesizable small molecules, DOBs can be potentially developed into clinical and industrial antioxidants. Crown Copyright
- Ng, Lean-Teik,Ko, Horng-Huey,Lu, Tzy-Ming
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experimental part
p. 4360 - 4366
(2009/10/17)
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- Synthesis and evaluation of derrubone and select analogues
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(Chemical Equation Presented) Recently, we reported that the natural product derrubone exhibits Hsp90 inhibitory activity. Due to its unique architectural scaffold and proposed rapid assembly, the synthesis of this natural product was pursued with the aim of identifying structure-activity relationships. Synthesis of the natural product was accomplished in eight highly convergent steps, which led to a facile method for the construction of related compounds. Biological evaluation of derrubone and its analogues identified several compounds that exhibit low micromolar inhibitory activity against breast and colon cancer cell lines.
- Hastings, Jedidiah M.,Hadden, M. Kyle,Blagg, Brian S. J.
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p. 369 - 373
(2008/09/17)
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- Microwave-promoted synthesis of polyhydroxydeoxybenzoins in ionic liquids
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A microwave-promoted synthesis of polyhydroxydeoxybenzoins and -phenylpropanones has been developed, using bis{(trifluoromethyl)sulfonyl}amine (HNTf2) or BF3·OEt2 in an ionic liquid solvent.
- Hakala, Ullastiina,W?h?l?, Kristiina
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p. 8375 - 8378
(2007/10/03)
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- PREPARATION METHOD OF 2-PHENYLACETOPHENONE DERIVATIVES
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Disclosed is a preparation method of 2-phenylacetophenone derivatives which are used as key intermediates in total syntheses of coumestans and isoflavonoids such as coumestrol, genistein and daidzein which are phytoestrogens contained in soybean and black
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Page/Page column 9
(2008/06/13)
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- Synthesis of analogs of natural isoflavonoids containing phloroglucinol
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Analogs of the natural isoflavonoids biochanin A and orobol were synthesized. Alkylation involving phenolic hydroxyls and the chromone ring was studied.
- Bondarenko,Levenets,Frasinyuk,Khilya
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p. 271 - 275
(2007/10/03)
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- Estrogens for treating ALS
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A method for preventing and treating ALS by administering a phytoestrogen, preferably genistein.
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- The first isolation and crystal structure of a boron difluoro complex (isoflavone yellow). Biologically active intermediates produced during isoflavone synthesis
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The yellow intermediate 4f produced during the reaction of the deoxybenzoin 3f with N,N'-dimethyl(chloromethylene)ammonium chloride in the presence of BF3*Et2O prior to the formation of the corresponding isoflavone was isolated for the first time and characterized by NMR, MS and single-crystal X-ray diffraction techniques. These yellow intermediates showed anticancer, nematicidal and mosquitocidal activities.
- Balasubramanian, Sreenivasan,Ward, Donald L.,Nair, Muraleedharan G.
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p. 567 - 570
(2007/10/03)
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- A facile synthesis of 2-substituted isoflavones for immunoassay: Assembly of the isoflavonoid skeleton by means of a novel cyclisation reaction
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For the purpose of the development of immunoassays for wide-scale screening, isoflavones suitable for attachment to a hapten were prepared. A new cyclisation reaction allowed the direct conversion of 2- (acyloxy)deoxybenzoins to 2-alkylisoflavones by treatment with chlorotrimethylsilane and triethylamine in dimethylformamide.
- Pelter, Andrew,Ward, Robert S.,Whalley, Jacqueline L.
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p. 1793 - 1802
(2007/10/03)
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- Microwave-Mediated Synthesis of Anticarcinogenic Isoflavones from Soybeans
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Soybean isoflavonoids, 7,4'-dihydroxyisoflavone (daidzein), 7-hydroxy-4'-methoxyisoflavone (formononetin), 5,7,4'-trihydroxyisoflavone (genistein), and 5,7-dihydroxy-4'-methoxyisoflavone (biochanin A), were synthesized in high yields by cyclization of their corresponding ketones in a conventional microwave oven. Keywords: Microwave synthesis; isoflavones; daidzein; genistein; formononetin; biochanin A
- Chang, Yu-Chen,Nair, Muraleedharan G.,Santell, Ross C.,Helferich, William G.
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p. 1869 - 1871
(2007/10/02)
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- Synthesis of deoxybenzoins
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Zinc chloride-phosphoryl chloride is an efficient condensing agent for the preparation of hydroxy(methoxy)deoxybenzoins at room temperature directly from phenols and arylacetic acids.
- Devi, Nirada,Jain, Niveta,Krishnamurty, H. G.
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p. 874 - 875
(2007/10/02)
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