- Hydrogen bonding and π-π stacking in dimethylgenistein
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The title compound, 5-hydroxy-4′,7-dimethoxyisoflavone, Q 17H14O5, is composed of a benzopyranone moiety, a phenyl moiety and two methoxy groups. The benzopyranone ring is not coplanar with the phenyl ring, the dihedral an
- Zhang, Zun-Ting,Wang, Xiao-Bing,Liu, Qian-Guang,Zheng, Jian-Bin,Yu, Kai-Bai
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- Synthesis, Characterization, and Antiradical Activity of 6-Hydroxygenistein
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A convergent synthesis route of 6-hydroxygenistein (6-OHG) was reported, starting from cheap and readily available biochanin A, via methylation, bromination, methoxylation, and demethylation. The structure of the products was confirmed by MS, IR, 1/
- Shao, Jin,Zhao, Tong,Ma, Hui-Ping,Jia, Zheng-Ping,Jing, Lin-Lin
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p. 821 - 826
(2020/09/21)
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- Application of Mannich bases to the synthesis of hydroxymethylated isoflavonoids as potential antineoplastic agents
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The regiospecific Mannich aminomethylation of 7-hydroxyisoflavonoids using bis(N,N-dimethylamino)methane afforded C-8 substituted N,N-dimethylaminomethyl adducts, and the regioselective aminomethylation of 5-hydroxy-7-methoxyisoflavonoids afforded predomi
- Frasinyuk, Mykhaylo S.,Mrug, Galyna P.,Bondarenko, Svitlana P.,Sviripa, Vitaliy M.,Zhang, Wen,Cai, Xianfeng,Fiandalo, Michael V.,Mohler, James L.,Liu, Chunming,Watt, David S.
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p. 11292 - 11301
(2015/11/27)
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- Synthesis and cytotoxic activity of genistein derivatives
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A series of genistein derivatives was prepared and tested in vitro against leukocythemia (HL-60), colorectal adenocarcinoma (HT-29), and human gastric adenocarcinoma (SGC-7901) cell lines. Among these derivatives, 4′,5-di-n-octoxy-7-gem-difluoromethylenegenistein, 9f, had the strongest activity against HL-60, HT-29, and SGC-7901 cells.[Figure not available: see fulltext.]
- Zheng, Xing,Yao, Xu,Liu, Yunmei,Zheng, Zitong,Cao, Jianguo,Liao, Duanfang
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experimental part
p. 1296 - 1306
(2011/10/12)
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- Biotransformation of isoflavones by the larvae of the common cutworm (Spodoptera litura)
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Biotransformation of the 5,7,4′-trimethoxyisoflavone (1), 6,7,4′-trimethoxyisoflavone (2), and 7,4′-dimethoxyisoflavone (3) by insects, Spodoptera litura was investigated. Compound 1 was transformed to 5-hydroxy-7,4′-dimethoxyisoflavone (4), 7-hydroxy-5,4
- Takahashi, Koji,Araki, Hideo,Miyazawa, Mitsuo
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p. 719 - 721
(2007/10/03)
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- Genistein derivatives as selective estrogen receptor modulators: Sonochemical synthesis and in vivo anti-osteoporotic action
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Genistein derivatives were synthesized from genistein through a facile sonochemical approach in high yields. The bioassay was performed on ovariectomized (OVX) rats in terms of bone mineral density (BMD) and the weight of bone ash (WBA) to lead to the discovery of eight novel genistein-based selective estrogen receptor modulators. Attention to the structure-activity relationship disclosed that the newly introduced 2-hydroxyethylthio scaffolds were essential for the anti-osteoporotic activity. Moreover, the anti-osteoporotic action of genistein, deprivable by methylation, could be restored and enhanced by subsequent sulfonation. The most promising compound was 4′,5,7-tri[3-(2-hydroxyethylthio)propoxy]isoflavone, displaying 24% (or 8%) increment in BMD and 31% (or 11%) increase in WBA of the femora relative to those discerned with the OVX (or genistein) group. Acute toxicity test showed that none of the active compounds was acutely toxic.
- Wang, Shi F.,Jiang, Qing,Ye, Yong H.,Li, Yang,Tan, Ren X.
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p. 4880 - 4890
(2007/10/03)
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- Study of sophoricoside derivatives with the aid of lanthanoid shift reagents
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Acylated and methylated derivatives of sophoricoside and of genistein have been synthesized, and their interaction in solution with the lanthanoid shift reagent (LSR) Eu(FOD)3 has been studied. For 5-O-alkyl derivatives of genistein an anomalous broadening of the 1H NMR signals was observed in the presence of the LSR, which is explained by the formation with the LSR of a chelate having a low rate of dissociation. The temperature and concentration dependencies of the paramagnetic broadenings of the signals have been studied.
- Turov,Bondarenko,Khilya
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p. 535 - 538
(2007/10/03)
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- Studies on Zoospore-Attracting Activity. I. Synthesis of Isoflavones and Their Attracting Activity to Aphanomyces euteiches Zoospore
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Prunetin (2) and its derivatives were synthesized in order to study the relationship between structure and attracting activity to Aphanomyces euteiches zoospore.All of the derivatives (1, 2, 4 and 6), which had a hydroxyl group at the C-5 position in the isoflavone, showed attracting activity, but the methyl ether derivatives (3, 5, 7 and 8) do not have or have very weak attracting activity.The isoflavones (1, 2, and 4) with strong attracting activity also had estrogenic activity.Keywords - isoflavone; prunetin; genistein; biochanin A; 5-methylgenistein; 5-hydroxy-4',7-dimethoxyisoflavone; Aphanomyces euteiches; zoospore; attracting activity; estrogenic activity
- Sekizaki, Haruo,Yokosawa, Ryozo
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p. 4876 - 4880
(2007/10/02)
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