- Study on the synthesis, antioxidant properties, and self-assembly of carotenoid–flavonoid conjugates
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Flavonoids and carotenoids possess beneficial physiological effects, such as high antioxidant capacity, anticarcinogenic, immunomodulatory, and anti-inflammatory properties, as well as protective effects against UV light. The covalent coupling of hydropho
- Línzembold, Ildikó,Czett, Dalma,B?ddi, Katalin,Kurtán, Tibor,Király, Sándor Balázs,Gulyás-Fekete, Gergely,Takátsy, Anikó,Lóránd, Tamás,Deli, József,Agócs, Attila,Nagy, Veronika
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- Nickel-catalyzed methylation of aryl halides/tosylates with methyl tosylate
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This work describes the cross-electrophile methylation of aryl bromides and aryl tosylates with methyl tosylate. The mild reaction conditions allow effective methylation of a wide set of heteroaryl electrophiles and dimethylation of dibromoarenes.
- Wang, Jiawang,Zhao, Jianhong,Gong, Hegui
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supporting information
p. 10180 - 10183
(2017/09/23)
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- SYNTHESIS OF ISOFLAVANES AND INTERMEDIATES THEREOF
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Subject of the invention is a method for enantioselective production of an isoflavane from an isoflavone, comprising the steps: (a) selectively reducing the isoflavone, such that the 4-keto group of the isoflavone is converted to a 4-hydroxy group, and the 2,3-double bond of the isoflavone is converted to a 2,3-single bond, thereby obtaining a 4-hydroxy intermediate, and (b) reacting the 4-hydroxy intermediate with a chiral reagent, such that a chiral group is covalently attached to the C4-position of the 4-hydroxy intermediate, thereby obtaining a chiral intermediate. The invention also relates to intermediates of formulae (IV), (V), (VI) and (VII) obtainable in the inventive process.
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Page/Page column 23
(2016/04/20)
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- Synthetic method for equol
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The invention provides a synthetic method for equol. The synthetic method comprises the following steps: with daidzein as a raw material, subjecting daidzein to an esterification reaction to obtain a compound B; subjecting the compound B to olefinic-bond conjugation and a reduction reaction of a carbonyl group so as to obtain a compound C; subjecting the compound C to a dehydration reaction so as to obtain a compound D; and carrying out double-bond hydrogenation on the compound D so as to obtain equol. The synthetic method provided by the invention has the advantages of short synthesis steps, simple operation, economic performance, environmental protection, yield of 70% or above in each step, obviously increased overall yield and suitability for industrial mass production.
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Paragraph 0055; 0056
(2016/10/10)
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- Phosphoramidate protides of five flavones and their antiproliferative activity against HepG2 and L-O2 cell lines
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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.
- Li, Yue-Qing,Yang, Fei,Wang, Liu,Cao, Zhi,Han, Tian-Jiao,Duan, Zhe-Ang,Li, Zhen,Zhao, Wei-Jie
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p. 196 - 208
(2016/05/02)
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- Synthesis of oxygenated 4-arylisoflavans and 4-arylflavans
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Oxygenated 4-arylisoflavans and 4-heteroarylisoflavans were synthesized in good yields via BF3·OEt2 catalyzed arylation reactions of 4′,7-diacetoxyisoflavan-4-ol 8 with activated aryl and heteroaryl compounds. These reactions were found to produce stereoselectively the trans isomers. Similar reactions of 4′,7-diacetoxyflavan-4-ol 16 afforded the corresponding 4-arylflavans and 4-heteroarylflavans as mixtures of cis/trans isomers.
- Deodhar, Mandar,Wood, Kasey,Black, David Stc,Kumar, Naresh
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p. 6697 - 6700,4
(2012/12/13)
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- Synthesis of oxygenated 4-arylisoflavans and 4-arylflavans
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Oxygenated 4-arylisoflavans and 4-heteroarylisoflavans were synthesized in good yields via BF3·OEt2 catalyzed arylation reactions of 4′,7-diacetoxyisoflavan-4-ol 8 with activated aryl and heteroaryl compounds. These reactions were found to produce stereoselectively the trans isomers. Similar reactions of 4′,7-diacetoxyflavan-4-ol 16 afforded the corresponding 4-arylflavans and 4-heteroarylflavans as mixtures of cis/trans isomers.
- Deodhar, Mandar,Wood, Kasey,Black, David Stc,Kumar, Naresh
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p. 6697 - 6700
(2013/01/15)
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- Retinylisoflavonoid as a novel membrane antioxidant
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We report a novel molecular dyad as an antioxidant, retinylisoflavonoid, with a retinal analogue C22-aldehyde and the isoflavonoid daidzein covalently linked. Its physicochemical properties, pKa (pK a1 = 8.45, pKa2 = 11.42), oxidation potential (1.03 V vs NHE), and Log10 partition (Log P = 1.96), as well as the Trolox equivalent antioxidant capacity (TEAC = 0.4), have been characterized. Spectroscopic and quantum chemical investigations have revealed the following unique structural characters: (i) Either free in solution or included in liposomal membranes, the C22-aldehyde moiety of retinylisoflavonoid is coplanar with the B-ring of daidzein owing to the strong intramolecular hydrogen bonding C 14-=O···HO-B4′. Accordingly, the C 22-aldehyde moiety extends its π-conjugation significantly to the B-ring. (ii) The inherent amphiphilicity of retinylisoflavonoid allows the C22-aldehyde moiety embedded in the lipid phase of the liposomes, whereas the daidzein counterpart stays at the membrane surface, in effect facilitating interior-to-surface radical communication. As the result, the antilipooxidation activity of retinylisoflavonoid is improved significantly in protecting membrane lipids compared to the parent compounds alone or in combination, and importantly, the performance is more prominent under higher-level oxidative stress. This work provides an advanced case study of new antioxidant development based on optimized electronic and molecular structures.
- An, Cun-Bin,Liang, Ran,Ma, Xiao-Hua,Fu, Li-Min,Zhang, Jian-Ping,Wang, Peng,Han, Rui-Min,Ai, Xi-Cheng,Skibsted, Leif H.
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experimental part
p. 13904 - 13910
(2011/03/16)
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- Production of isoflavone derivatives
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Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.
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Page/Page column 5
(2008/06/13)
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- Isoaurostatin: Total synthesis and structural revision
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Isoaurostatin, a topoisomerase I inhibitor isolated from Thermomonospora alba has been synthesized for the first time from 2,4-dihydroxyacetophenone via 6-methoxybenzo-2(3H)-furanone in five steps. The E-isomer was converted into Z-isomer, but spectroscopic data of either of these two isomers did not match with those of the natural product. The structure of isoaurostatin has been revised to a known isoflavone, daidzein (2), based on careful analysis of spectroscopic data.
- Venkateswarlu, Somepalli,Panchagnula, Gopala K.,Guraiah, Mothukuri Bala,Subbaraju, Gottumukkala V.
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p. 3013 - 3017
(2007/10/03)
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- Hydrogen bonds and π-π stacking interaction in 4′, 7-dimethoxylisoflavone and 4′,7-diacetyl-O-isoflavone
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4′,7-dimethoxylisoflavone, C17H14O4, (I), is linked into a supramolecular structure by a variety of weak but direction-specific intermolecular forces, the molecules are linked into chains through C-H...O hydrogen bonds, th
- Zhang, Zun-Ting,Wang, Xiao-Bing,Wang, Qiu-Ya,Wu, Li-Na
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p. 923 - 929
(2007/10/03)
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- Dietary phytoestrogens and their synthetic structural analogues as calcium channel blockers in human platelets.
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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.
- Dobrydneva, Yuliya,Williams, Roy L,Morris, Gary Z,Blackmore, Peter F
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p. 399 - 410
(2007/10/03)
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