- Metabolic studies of four soy isoflavones in rats by HPLC-HR-MS
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In this paper, the metabolites of four soy isoflavones, daidzein, daidzin, genistein, and genistin, on perfused rat intestine-liver model were investigated by high-performance liquid chromatography coupled with high-resolution mass spectrometer/tandem mass spectrometer. Totally 16 metabolites were detected and identified based on accurate mass, fragmentation patterns, and multiple-stage mass data (MSn). The metabolic site of dadzein-7-methyl ether (D-7-M) was further confirmed by nuclear magnetic resonance. Methylation, glucuronide conjugation, and sulfate conjugation were the primary metabolic processes. Among them, six metabolites, daidzin-4′,7-diglucoside, genistein-4′- glucoside, D-7-M, dadzein-4′,7-dimethyl ether, genistein-4′-methyl ether, and genistein-7-methyl ether were detected in rats for the first time and not reported in humans. The metabolic pathways of daidzein, daidzin genistein, and genistin in rats were postulated. The biological effects of these metabolites are worthy of further investigation.
- Li, Ying-Fei,Ren, Qiang,Jin, Ying,Wu, Cai-Sheng,Wang, Cai-Hong,Jia, Zhi-Xin,Zhang, Jin-Lan
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Read Online
- New scheme of the biosynthesis of formononetin involving 2,7,4′-trihydroxyisoflavanone but not daidzein as the methyl acceptor
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Glycyrrhiza echinata cell-free extract produced isoformononetin by the 7-O-transmethylation of daidzein from S-adenosyl-L-methionine (SAM). When the yeast microsome expressing 2-hydroxyisoflavanone synthase was mixed with the cell-free extract and incubated with liquiritigenin and SAM, formononetin emerged. Furthermore, the cell-free extract yielded formononetin on incubation with 2,7,4′-trihydroxyisoflavanone and SAM. We propose a novel pathway of formononetin biosynthesis involving 2,7,4′-trihydroxyisoflavanone as the methyl acceptor.
- Akashi, Tomoyoshi,Sawada, Yuji,Aoki, Toshio,Ayabe, Shin-Ichi
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Read Online
- INDUCIBLY-FORMED ISOFLAVONOIDS FROM LEAVES OF SOYBEAN
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Isoformononetin, glyceollins I, II and III, and 2-isopentenyl-3,6α,9-trihydroxypterocarpan (glyceocarpin) accumulated in soybean (Glycine max) leaves after treatment with aqueous sodium iodoacetate or a cell suspension of the bacterium, Pseudomonas pisi.These compounds were also accompanied by two previously unreported pterocarpans, glycerofuran and its 9-O-methyl derivative.Glyceocarpin is described for the first time as a plant product.Key Word Index- Glycine max; Leguminosae; soybean; Pseudomonas pisi; isoflavonoids; pterocarpans; isoflavone; phytoalexins; antibacterial activity.
- Ingham, John L.,Keen, Noel T.,Mulheirn, Lawrence J.,Lyne, Robert L.
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Read Online
- Scope and Applications of 2,3-Oxidative Aryl Rearrangements for the Synthesis of Isoflavone Natural Products
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The reaction of flavanones with hypervalent iodine reagents was investigated with a view to the synthesis of naturally occurring isoflavones. In contrast to several previous reports in the literature, we did not observe the formation of any benzofurans via a ring contraction pathway, but could isolate only isoflavones, resulting from an oxidative 2,3-aryl rearrangement, and flavones, resulting from an oxidation of the flavanones. Although the 2,3-oxidative rearrangement allows a synthetically useful approach toward some isoflavone natural products due to the convenient accessibility of the required starting materials, the overall synthetic utility and generality of the reaction appear to be more limited than previous literature reports suggest.
- Kwesiga, George,Schmidt, Bernd,Sperlich, Eric
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p. 10699 - 10712
(2021/08/20)
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- Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation
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In this study, polyhydroxyisoflavones that directly prevent the aggregation of both amyloid β (Aβ) and tau were expediently synthesized via divergent Pd(0)-catalyzed Suzuki-Miyaura coupling and then biologically evaluated. By preliminary structure–activity relationship studies using thioflavin T (ThT) assays, an ortho-catechol containing isoflavone scaffold was proven to be crucial for preventing both Aβ aggregation and tau-mediated neurofibrillary tangle formation. Additional TEM experiment confirmed that ortho-catechol containing isoflavone 4d significantly prevented the aggregation of both Aβ and tau. To investigate the mode of action (MOA) of 4d, which possesses an ortho-catechol moiety, 1H-15N HSQC NMR analysis was thoroughly performed and the result indicated that 4d could directly inhibit both the formation of Aβ42 fibrils and the formation of tau-derived neurofibrils, probably through the catechol-mediated nucleation of tau. Finally, 4d was demonstrated to alleviate cognitive impairment and pathologies related to Alzheimer's disease in a 5XFAD transgenic mouse model.
- Do, Ji Min,Gee, Min Sung,Inn, Kyung-Soo,Kim, Jong-Ho,Kim, Nam Kwon,Kim, Nam-Jung,Lee, Hyun Woo,Lee, Jong Kil,Seo, Min-Duk,Seong, Ji Hye,Son, Seung Hwan,Yoo, Hyung-Seok,Yoo, Ji-Na
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- Structure-guided design and synthesis of isoflavone analogs of GW4064 with potent lipid accumulation inhibitory activities
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Our group has previously reported a series of isoflavone derivatives with antidyslipidemic activity. With this background, a series of isoflavone analogs of GW4064 were designed, synthesized and evaluated the lipid-lowering activity of analogs. As a result, most of compounds significantly reduced the lipid accumulation in 3T3-L1 adipocytes and four of them (10a, 11, 15c and 15d) showed stronger inhibitory than GW4064. The most potent compound 15d exhibited promising agonistic activity for FXR in a cell-based luciferase reporter assay. Meanwhile, 15d up-regulated FXR, SHP and BSEP gene expression and down-regulated the mRNA expression of lipogenesis gene SREBP-1c. Besides, an improved safety profile of 15d was also observed in a HepG2 cytotoxicity assay compared with GW4064. The obtained biological results were further confirmed by a molecular docking study showing that 15d fitted well in the binding pocket of FXR and interacted with some key residues simultaneously.
- Qiu, Rongmao,Luo, Guoshun,Cai, Xuerong,Liu, Linyi,Chen, Mingqi,Chen, Deying,You, Qidong,Xiang, Hua
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p. 3726 - 3730
(2018/10/20)
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- Novel isoflavone derivative, preparation method therefor and medicinal use of novel isoflavone derivative
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The invention relates to the field of pharmaceutical chemistry, relates to an isoflavone derivative, a preparation method therefor and medicinal use of the novel isoflavone derivative and particularlyrelates to isoflavone derivatives represented by a general formula (I) shown in the description, preparation methods therefor, pharmaceutical compositions containing these compounds and medicinal useof the isoflavone derivatives and the pharmaceutical compositions, particularly use of drugs for preventing or treating hyperlipidemia, type II diabetes, atherosclerosis and non-alcoholic fatty hepatitis.
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Paragraph 0066-0067; 0071-0073
(2018/07/30)
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- CYTISINE-LINKED ISOFLAVONOID ANTINEOPLASTIC AGENTS FOR THE TREATMENT OF CANCER
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Cytisine-linked isoflavonoids, or pharmaceutically acceptable salts thereof or pharmaceutically acceptable compositions thereof, are useful for the treatment of conditions in which cells have a reliance on peroxisomal HSD17B4 to degrade very long chain fatty acids and provide necessary energy for cell proliferation, such as is seen in colorectal cancer and prostate cancer, for example.
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Paragraph 0057; 0059
(2019/01/04)
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- Developing antineoplastic agents that target peroxisomal enzymes: Cytisine-linked isoflavonoids as inhibitors of hydroxysteroid 17-beta-dehydrogenase-4 (HSD17B4)
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Cytisine-linked isoflavonoids (CLIFs) inhibited PC-3 prostate and LS174T colon cancer cell proliferation by inhibiting a peroxisomal bifunctional enzyme. A pull-down assay using a biologically active, biotin-modified CLIF identified the target of these agents as the bifunctional peroxisomal enzyme, hydroxysteroid 17β-dehydrogenase-4 (HSD17B4). Additional studies with truncated versions of HSD17B4 established that CLIFs specifically bind the C-terminus of HSD17B4 and selectively inhibited the enoyl CoA hydratase but not the d-3-hydroxyacyl CoA dehydrogenase activity. HSD17B4 was overexpressed in prostate and colon cancer tissues, knocking down HSD17B4 inhibited cancer cell proliferation, suggesting that HSD17B4 is a potential biomarker and drug target and that CLIFs are potential probes or therapeutic agents for these cancers.
- Frasinyuk, Mykhaylo S.,Zhang, Wen,Wyrebek, Przemyslaw,Yu, Tianxin,Xu, Xuehe,Sviripa, Vitaliy M.,Bondarenko, Svitlana P.,Xie, Yanqi,Ngo, Huy X.,Morris, Andrew J.,Mohler, James L.,Fiandalo, Michael V.,Watt, David S.,Liu, Chunming
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supporting information
p. 7623 - 7629
(2017/09/27)
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- Repurposing Hsp90 inhibitors as antibiotics targeting histidine kinases
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To address the growing need for new antimicrobial agents, we explored whether inhibition of bacterial signaling machinery could inhibit bacterial growth. Because bacteria rely on two-component signaling systems to respond to environmental changes, and because these systems are both highly conserved and mediated by histidine kinases, inhibiting histidine kinases may provide broad spectrum antimicrobial activity. The histidine kinase ATP binding domain is conserved with the ATPase domain of eukaryotic Hsp90 molecular chaperones. To find a chemical scaffold for compounds that target histidine kinases, we leveraged this conservation. We screened ATP competitive Hsp90 inhibitors against CckA, an essential histidine kinase in Caulobacter crescentus that controls cell growth, and showed that the diaryl pyrazole is a promising scaffold for histidine kinase inhibition. We synthesized a panel of derivatives and found that they inhibit the histidine kinases C. crescentus CckA and Salmonella PhoQ but not C. crescentus DivJ; and they inhibit bacterial growth in both Gram-negative and Gram-positive bacterial strains.
- Vo, Chau D.,Shebert, Hanna L.,Zikovich, Shannon,Dryer, Rebecca A.,Huang, Tony P.,Moran, Lindsey J.,Cho, Juno,Wassarman, Douglas R.,Falahee, Bryn E.,Young, Peter D.,Gu, Garrick H.,Heinl, James F.,Hammond, John W.,Jackvony, Taylor N.,Frederick, Thomas E.,Blair, Jimmy A.
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supporting information
p. 5235 - 5244
(2017/11/01)
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- Synthesis, crystal structure, characterization and antifungal activity of 3,4-diaryl-1H-Pyrazoles derivatives
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A series of 3,4-diaryl-1H-pyrazoles derivatives were designed and synthesized by the reaction of 3-heteroarylchromones and 3-phenylchromones with hydrazine hydrate in good yields. All of those compounds were characterized by 1H NMR, 13C NMR, IR, and HRMS. Moreover, 3-(2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-1H-pyrazole and 3-(2,4-dihydroxy phenyl)-4-(4-methoxyphenyl)-1H-pyrazole were further conformed by the single crystal X-ray diffraction. In addition, the antifungal activity against five phytopathogenic fungi (Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani and Fusarium solani) of 3,4-diaryl-1H-pyrazoles were evaluated. 3-(2-Hydroxy-4-isopropoxyphenyl)-4-phenyl-1H-pyrazole was more better and broader inhibitory effect on Cytospora sp., C. gloeosporioides, A. solani and Fusarium solani with IC50 values of 26.96, 28.84, 16.77 and 22.10 μg/mL, respectively. 4-(4-Fluorophenyl)-3-(2-hydroxy-4-methoxyphenyl)-1H-pyrazole exhibited fairly effective antifungal activity against Cytospora sp., C. gloeosporioides and A. solani with IC50 values of 11.91, 14.92 and 16.98 μg/mL, respectively.
- Zhang, Jin,Tan, Da-Jin,Wang, Tao,Jing, Si-Si,Kang, Yang,Zhang, Zun-Ting
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p. 235 - 242
(2017/08/09)
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- Design and synthesis of 3-arylbenzopyran based non-steroidal vitamin-D3 mimics as osteogenic agents
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3-Arylbenzopyran based non-steroidal osteogenic agents have been explored as structural templates of estrogen and vitamin-D3. The target molecules 18a-c, 19a-c, 26a-c, 27a-c and intermediates 17a-c and 25a-c were studied for their osteogenic activity in an osteoblast differentiation assay in vitro using mouse calvarial osteoblast cells. Compounds 25c, 26b, 27b and 27c effectively increased ALP activity at 1 pM concentration compared to the untreated cells. The active compounds were devoid of inherent toxicity at 1 pM concentration in osteoblast cells. The most active compound, 27b, was studied for mineralization of osteoblast cells and expression of marker genes, viz. BMP-2, RUNX-2 & Osx, involved in osteogenesis. Molecular docking analysis performed for 27b showed its possible interactions with estrogen receptor-α and -β (ER-α and ER-β) as well as the vitamin-D receptor (VDR).
- Ahmad, Mohd. Imran,Raghuvanshi, Dushyant Singh,Singh, Sarita,John, Aijaz A.,Prakash, Ravi,Nainawat, Kripa Shankar,Singh, Divya,Tripathi, Shubhandra,Sharma, Ashok,Gupta, Atul
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p. 2381 - 2394
(2016/12/18)
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- Combinatorial synthesis of structurally diverse triazole-bridged flavonoid dimers and trimers
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Flavonoids are a large family of compounds associated with a broad range of biologically useful properties. In recent years, synthetic compounds that contain two flavonoid units linked together have attracted attention in drug discovery and development projects. Numerous flavonoid dimer systems, incorporating a range of monomers attached via different linkers, have been reported to exhibit interesting bioactivities. From a medicinal chemistry perspective, the 1,2,3-triazole ring system has been identified as a particularly attractive linker moiety in dimeric derivatives (owing to several favourable attributes including proven biological relevance and metabolic stability) and triazole-bridged flavonoid dimers possessing anticancer and antimalarial activities have recently been reported. However, there are relatively few examples of libraries of triazole-bridged flavonoid dimers and the diversity of flavonoid subunits present within these is typically limited. Thus, this compound type arguably remains underexplored within drug discovery. Herein, we report a modular strategy for the synthesis of novel and biologically interesting triazole-bridged flavonoid heterodimers and also very rare heterotrimers from readily available starting materials. Application of this strategy has enabled step-efficient and systematic access to a library of structurally diverse compounds of this sort, with a variety of monomer units belonging to six different structural subclasses of flavonoid successfully incorporated.
- Sum, Tze Han,Sum, Tze Jing,Galloway, Warren R. J. D.,Collins, Súil,Twigg, David G.,Hollfelder, Florian,Spring, David R.
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- Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals
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The aminomethylation of hydroxylated isoflavones with 2-aminoethanol, 3-amino-1-propanol, 4-amino-1-butanol, and 5-amino-1-pentanol in the presence of excess formaldehyde led principally to 9-(2-hydroalkyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]-oxazin-4-ones 4 and/or the tautomeric 7-hydroxy-8-(1,3-oxazepan-3-ylmethyl)-4H-chromen-4-ones 5. The ratio of these tautomers was dependent on solvent polarity, electronic effects of aryl substituents in the isoflavone and the structure of the amino alcohol. NMR studies confirmed the interconversion of tautomeric forms.
- Frasinyuk, Mykhaylo S.,Bondarenko, Svitlana P.,Khilya, Volodymyr P.,Liu, Chunming,Watt, David S.,Sviripa, Vitaliy M.
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p. 1053 - 1067
(2015/08/03)
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- Novel daidzein analogs and their in vitro anti-influenza activities
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A series of novel isoflavonoids were synthesized based on structural modifications of daidzein, an active ingredient of traditional Chinese medicine (TCM) and evaluated for their anti-influenza activity, in vitro, against H1N1 Tamiflu-resistant (H1N1 TR) virus in the MDCK cell line. Among them, 4-oxo-4H-1-benzopyran-8-carbaldehydes 11a-11g were most promising, and they demonstrated better activities and selectivities comparable to those the reference ribarivin, a nucleoside antiviral agent. 3-(4-Bromophenyl)-7-hydroxy-4-oxo-4H-1-benzopyran-8-carboxaldehyde (11c) displayed the best inhibitory activity (EC50, 29.0 μM) and selectivity index (SI>10.3). Analysis of the structure￡activity relationships (SAR) indicated that both the non-naturally-occurring Br-substituted B-ring and appropriate CHO and OH groups on the A-ring might be critical for the activity and selectivity against H1N1 TR influenza viruses.
- Chung, Shu-Ting,Huang, Yi-Ting,Hsiung, Hsin-Yi,Huang, Wen-Hsin,Yao, Chen-Wen,Lee, An-Rong
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p. 685 - 696
(2015/04/27)
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- New para-substituted non-symmetric isoflavones for their fast photo-switching ability: Synthesis and their liquid crystal characterization
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The first example of non-symmetric isoflavone-based fast photo-switchable liquid crystals with different functional groups at the terminal position were synthesized and characterized. Polarizing optical microscopy study revealed that the compounds showed least ordered nematic phase. Optical photo switching study exhibited very fast photoisomerization effect in solution. The E-Z and Z-E conversion occurred around 3-5 s and 40-700 s respectively. This is also the first example of para-substituted non-symmetric isoflavone liquid crystals exhibiting very fast photo switching property in solution. Argument based on non-symmetrical behaviour might be the reason for the observed behaviour.
- Yuvaraj,Yam, Wan Sinn,Chan, Tze Nee,Goh, Yit Peng,Hegde, Gurumurthy
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p. 1115 - 1122
(2014/11/12)
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- Chevalierinoside a: A new isoflavonoid glycoside from the stem bark of Antidesma chevalieri Beille (euphorbiaceae)
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Chevalierinoside A (1), a new isoflavonoid glycoside determined as biochanin A 7-O- [α-L-rhamnopyranosyl-1→6-β-D-apiofuranosyl- 1→2-β-D-glucopyranoside], together with the known friedelin (2), friedelan-3β-ol (3) and betulinic acid (4), were isolated from
- Djouossi, Marie Genevieve,Tebou, Perrin Lanversin Foning,Mabou, Florence Declaire,Ngnokam, David,Tapondjou, Leon A.,Harakat, Dominique,Voutquenne-Nazabadioko, Laurence
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p. 309 - 314
(2014/06/24)
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- Novel synthesis of 3-phenyl-chromen-4-ones using n-heterocyclic carbene as organocatalyst: An efficient domino catalysis type approach
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Herein is reported a simple and efficient synthesis of isoflavones starting from various substituted phenacyl bromides and salicylaldehydes in presence of NHC. The mechanism involved domino catalysis type approach with consumption and regeneration of catalyst in two catalytic cycles. This method proved to be very lucrative and gives very good yield. The method described here represents an environmentally benign alternative to classical approach.
- Mishra, Priya,Singh, Sarita,Ankit, Preyas,Fatma, Shahin,Singh, Divya,Singh, Jagdamba
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p. 1070 - 1076
(2013/07/28)
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- A mild and efficient protocol to synthesize chromones, isoflavones, and homoisoflavones using the complex 2,4,6-trichloro-1,3,5-triazine/ dimethylformamide
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A mild and efficient one-flask method has been developed for the synthesis of chromones, isoflavones, and homoisoflavones from 2-hydroxyacetophenones, deoxybenzoins, and dihydrochalcones, respectively, via one-carbon extension using the complex 2,4,6-trichloro-1,3,5-triazine/dimethylformamide. Deoxybenzoins and dihydrochalcones were prepared in situ by the reaction of readily available substituted phenols with phenylacetic acids and 3-phenylpropanoic acids, respectively. This method allows the synthesis of a wide range of compounds with multiple phenolic hydroxyls and other substituents. The methodology has been applied to the synthesis of three naturally occurring isoflavones such as formononetin (9c), daidzein (9d), and retusin (9h).
- Basha, G. Mahaboob,Yadav, S. Kumar,Srinuvasarao,Prasanthi,Ramu,Mangarao,Siddaiah
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p. 763 - 768
(2013/08/23)
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- ISOFLAVONE FATTY ACID ESTER DERIVATIVES, PREPARATION METHOD AND PHARMACEUTICAL USES THEREOF
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Isoflavone fatty acid ester derivatives of formula (I) or (II), the preparation method thereof and the pharmaceutical compositions containing such compounds are disclosed. The uses of such compounds in preparation of medicaments for preventing or treating hyperlipidemia, obesity or type II diabetes are also disclosed.
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Paragraph 0092
(2013/04/10)
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- Synthesis and anti-tumor activities of novel oxazinyl isoflavonoids
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The design, synthesis and biological evaluation of a novel series of oxazinyl isoflavonoids is described. Several analogs were shown to exhibit growth inhibitory effects against SKOV-3, DU-145 and HL-60 human colon cancer cell lines with IC50 values in the micromolar range. The cellular potency of compounds 7e and 12h were found to have greater in vitro inhibitory activities than phenoxodiol, the parental compound currently in late-stage clinical trials for the treatment of cancer. The results shown are suitable for further lead optimization.
- Wang, Dun,Hou, Like,Wu, Lirong,Yu, Xin
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scheme or table
p. 513 - 520
(2012/05/05)
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- Deglycosylation of isoflavonoid glycosides from maackia amurensis cell culture by β-D-glucosidase from littorina sitkana hepatopancrease
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Maakia amurensis (strain A-18) cell culture synthesizes a significant quantity of isoflavonoids, a large part of which consists of isoflavone glucosides and malonylglucosides. β-D-Hydrolase enzyme complexes from the marine mollusk Littorina sitkana and the marine mycelial fungus P. canescens were used to obtain isoflavones from their conjugated forms. The specificity of β-D-glucanases from L. sitkana for various glycosides was studied. The deglycosylation efficiency depended on the aglycon structure. The deglycosylated fraction of isoflavonoids obtained from M. amurensis cell culture exhibited antitumor activity.
- Kusaikin,Zakharenko,Ermakova,Veselova,Grigoruk,Fedoreev,Zvyagintseva
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experimental part
p. 197 - 200
(2011/09/12)
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- Synthetic analogs of daidzein, having more potent osteoblast stimulating effect
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A series of didzein derivatives were synthesized and assessed for stimulation of osteoblast differentiation using primary cultures of rat calvarial osteoblasts. Data suggested that three synthetic analogs, 1c, 3a and 3c were several folds more potent than daidzein in stimulating differentiation and mineralization of osteoblasts. Further, these three compounds did not show any estrogen agonistic activity, however had mild estrogen antagonistic effect. Out of the three compounds, 3c was found to maximally increase the mineralization of bone marrow osteoprogenitor cells. Compound 3c also robustly increased the mRNA levels of osteogenic genes including bone morphogenetic protein-2 and osteocalcin in osteoblasts. Unlike daidzein, 3c did not inhibit osteoclastogenesis. Collectively, we demonstrate osteogenic activity of daidzein analogs at significantly lower concentrations than daidzein.
- Yadav, Dinesh K.,Gautam, Abnish K.,Kureel, Jyoti,Srivastava, Kamini,Sahai, Mahendra,Singh, Divya,Chattopadhyay, Naibedya,Maurya, Rakesh
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p. 677 - 681
(2011/03/18)
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- Active Compound Combinations
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Compositions comprising a (A) dithiino-tetracarboximide of formula (I) and at least one agriculturally beneficial biological control agent (B) are disclosed. A method for curatively or preventively controlling phytopathogenic fungi of plants or crops is disclosed. A method for treating seed and a method for protecting seed are disclosed.
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- Synthesis and structural study on heterocyclic compounds 7-decanoyloxy-3-(4′-substitutedphenyl)-4H-1-benzopyran-4-ones: Crystal structure of 7-decanoyloxy-3-(4′-methylphenyl)-4H-1-benzopyran-4-one
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Six new isoflavone-based esters, 7-decanoyloxy-3-(4′-substitutedphenyl)-4H-1-benzopyran-4-ones, derived from 1,3-benzenediol (resorcinol) and different para substituted phenylacetic acids have been synthesized and characterized. The molecular structures of the title compounds were elucidated with the employment of physical measurements and spectroscopic techniques (FTIR, 1D and 2D NMR). The conformation of 7-decanoyloxy-3-(4′-methylphenyl)-4H-1-benzopyran-4-one was determined by single crystal X-ray diffraction analysis of which the title compound crystallized into triclinic lattice with P-1 space group. Crystal structure of the title compound also revealed that the two phenyl rings of the central moiety were planar whilst the heterocyclic ring was found to pucker slightly from the mean plane.
- Yeap, Guan-Yeow,Yam, Wan-Sinn,Dominiak, Paulina,Ito, Masato M.
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experimental part
p. 25 - 33
(2010/06/16)
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- Processes for Preparing Isoflavonoids using 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran as a Starting Material
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Disclosed herein are processes for the preparation of isoflavonoids, in particular haginin E, equol, daidzein, formononetin and the like, in which 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran is used as a common starting material.
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Page/Page column 8-9
(2010/12/29)
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- Synthesis and biological evaluation of isoflavone fatty acid esters with potential weight loss and hypolipidemic activities
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A series of isoflavone fatty acid esters were designed on the basis of endogenous oleoyl-estrone using estrogen moiety modification strategy. Ten new compounds were synthesized, and their body weight loss and hypolipidemic bioactivities were assayed. Some of these novel compounds could effectively inhibit the differentiation of 3T3-L1 preadipocytes in vitro. The most potent compound 1a significantly decreased the body weight and white adipose tissue weight in a high-fat diet-induced rat model. Also, compound 1a showed good hypolipidemic activity and low toxicity.
- Xiang, Hua,Zhao, Wei,Xiao, Hong,Qian, Lei,Yao, Yao,Li, Xiao-Bo,Liao, Qing-Jiang
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experimental part
p. 3036 - 3042
(2010/07/06)
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- Synthesis of haginin E, equol, daidzein, and formononetin from resorcinol via an isoflavene intermediate
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New syntheses of haginin E, equol, daidzein, and formononetin are described in this Letter. Through a sequence of a Wittig reaction, O-alkylation, and another Wittig reaction, 4-benzyloxysalicylaldehyde, which was prepared from resorcinol in two steps, was converted into the desired diene in one pot. Subsequently, the prepared diene was subjected to ring-closing metathesis using Grubbs' catalyst (II) to construct the desired isoflavene intermediate. Using the prepared isoflavene, certain isoflavonoids such as haginin E, equol, daidzein, formononetin, and other related compounds were derived smoothly and in good overall yields.
- Li, Sie-Rong,Chen, Po-Yuan,Chen, Liang-Yeu,Lo, Yi-Fang,Tsai, Ian-Lih,Wang, Eng-Chi
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supporting information; experimental part
p. 2121 - 2123
(2009/07/26)
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- A Wacker-Cook synthesis of isoflavones: formononetine
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A total synthesis of the isoflavone formononetine 1 by an oxidative Pd-mediated cyclization of α-methylenedeoxybenzoins 4a-c is described. Substrates 4a-c were rapidly assembled using 'protected cyanohydrin' chemistry.
- Granados-Covarrubias, Evin H.,Maldonado, Luis A.
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scheme or table
p. 1542 - 1545
(2009/06/18)
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- 7-Hydroxy-benzopyran-4-one derivatives: A novel pharmacophore of peroxisome proliferator-activated receptor α and -γ (PPARα and γ) dual agonists
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Design, synthesis, and in vitro bioevaluation of a new class of potential dual PPARα and γ agonists discovered through a structure-driven design paradigm are described. The 7-hydroxy-benzopyran-4-one moiety (includes flavones, flavanones, and isoflavones) is the key pharmacophore of these novel molecules, exhibiting similarity to the core structure of both fibrates and thiazolidinediones. New lead PPAR ligands were identified from "natraceuticals" and synthetic analogues. In total, 77 molecules, including chalcones, flavones, flavanones, isoflavones, and pyrazole derivatives, were screened and structure-activity relationship studies of the dual agonists undertaken. Compounds 68, 70, 72, and 76 were identified as novel and potent dual PPARα and γ agonists. These novel molecules may have the potential to be the future leads in PPAR-related disorders, including type II diabetes mellitus and metabolic syndrome. 2009 American Chemical Society.
- Matin, Azadeh,Gavande, Navnath,Kim, Moon S.,Yang, Nancy X.,Salam, Noeris K.,Hanrahan, Jane R.,Roubin, Rebecca H.,Hibbs, David E.
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experimental part
p. 6835 - 6850
(2010/04/04)
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- FLAVONOID PPAR AGONISTS
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The present invention relates to PPAR agonists, and their use in therapy including the treatment of disease. In particular, the invention relates to flavonoid compounds which are PPAR-gamma agonists and/or PPAR alpha/gamma dual agonists.
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Page/Page column 36; 65
(2009/04/25)
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- Daidzein as an antioxidant of lipid: Effects of the microenvironment in relation to chemical structure
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Isoflavone daidzein (D, pKa1 = 7.47 ± 0.02 and pK a2 = 9.65 ± 0.07) was, through a study of the parent compound and its three methyl anisol derivatives 7-methyldaidzein (7-Me-D, pKa = 9.89 ± 0.05), 4'-methyldaidzein (4'-Me-D, pKa = 7.43 ± 0.03), and 7,4'-dimethyldaidzein (7,4'-diMe-D), found to retard lipid oxidation in liposomal membranes through two mechanisms: (i) radical scavenging for which the 4'-OH was more effective than the 7-OH group in agreement with the oxidation potentials: 0.69 V for 4'-OH and 0.92 V for 7-OH versus Ag/AgCl in acidic solution and 0.44 V for 4'-O- and 0.49 V for 7-O- in alkaline solution and (ii) change in membrane fluidity through incorporation of the isoflavones, in effect hampering radical mobility. The radical scavenging efficiency measured by the rate of the reaction with the ABTS?+ in aqueous solution followed the order D > 7-Me-D > 4'-Me-D > 7,4'-diMe-D, as also found for antioxidant efficiency in liposomes when oxidation was initiated with the water-soluble AAPH radical and monitored as the formation of conjugate dienes. For oxidation initiated by the lipid-soluble AMVN radical, the antioxidant efficiency was ranked as 4'-Me-D > D > 7,4'-diMe-D > 7-Me-D, and change in fluorescence anisotropy of fluorescent probes bound to the membrane surface or inside the lipid bilayer confirmed the effects of isoflavones on the membrane fluidity, especially for 7,4'-diMe-D.
- Liang, Jun,Tian, Yu-Xi,Fu, Li-Min,Wang, Tian-He,Li, Hai-Jun,Wang, Peng,Han, Rui-Min,Zhang, Jian-Ping,Skibsted, Leif H.
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experimental part
p. 10376 - 10383
(2010/03/25)
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- Practical and efficient entry to isoflavones by Pd(0)/C-mediated Suzuki-Miyaura reaction. Total synthesis of geranylated isoflavones
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A scalable synthesis of isoflavones taking advantage of the Suzuki-Miyaura reaction catalyzed by Pd(0)/C is described. The approach developed has been extended to the total synthesis of 7-O-geranylformononetin, griffonianone D, and conrauinone D, which did not display cytotoxicity against human HeLa carcinoma cells. In addition, this study established unambiguously the absolute configuration of natural griffonianone D.
- Felpin, Fran?ois-Xavier,Lory, Cécile,Sow, Hawaa,Acherar, Samir
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p. 3010 - 3016
(2007/10/03)
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- A convenient one-pot synthesis of 7-hydroxy-isoflavones from resorcinol with substituted phenylacetic acids
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A mild and highly efficient one-pot synthesis of 7-hydroxy-isoflavones is reported. The acylation of resorcinol with various phenyl acetic acids in molten zinc chloride affords an intermediate deoxybenzoin which without isolation is subjected to cyclization with N,N-dimethylformamide in the presence of boron trifluoride diethyl etherate and methanesulfonyl chloride to afford the 7-hydroxy-isoflavone without the formation of any by-product.
- Singh, Himanshu,Pratap, Ram
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p. 8161 - 8163
(2007/10/03)
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- Catalytic specificity of pea O-methyltransferases suggests gene duplication for (+)-pisatin biosynthesis
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S-adenosyl-l-methionine: 2-hydroxyisoflavanone 4′-O-methyltransferase (HI4′OMT) methylates 2,7, 4′-trihydroxyisoflavanone to produce formononetin, an essential intermediate in the synthesis of isoflavonoids with methoxy or methylenedioxy groups at carbon 4′ (isoflavone numbering). HI4′OMT is highly similar (83% amino acid identity) to (+)-6a-hydroxymaackiain 3-O-methyltransferase (HMM), which catalyzes the last step of (+)-pisatin biosynthesis in pea. Pea contains two linked copies of HMM with 96% amino acid identity. In this report, the catalytic activities of the licorice HI4′OMT protein and of extracts of Escherichia coli containing the pea HMM1 or HMM2 protein are compared on 2,7,4′-trihydroxyisoflavanone and enantiomers of 6a-hydroxymaackiain. All these enzymes produced radiolabelled 2,7-dihydroxy-4′-methoxyisoflavanone or (+)-pisatin from 2,7,4′-trihydroxyisoflavanone or (+)-6a-hydroxymaakiain when incubated with [methyl-14C]-S-adenosyl-l-methionine. No product was detected when (-)-6a-hydroxymaackiain was used as the substrate. HI4′OMT and HMM1 showed efficiencies (relative Vmax/Km) for the methylation of 2,7,4′-trihydroxyisoflavanone 20 and 4 times higher than for the methylation of (+)-6a-hydroxymaackiain, respectively. In contrast, HMM2 had a higher Vmax and lower Km on (+)-6a-hydroxymaackiain, and had a 67-fold higher efficiency for the methylation of (+)-6a-hydroxymaackiain than that for 2,7,4′-trihydroxyisoflavanone. Among the 15 sites at which HMM1 and HMM2 have different amino acid residues, 11 of the residues in HMM1 are the same as found in HI4′OMTs from three plant species. Modeling of the HMM proteins identified three or four putative active site residues responsible for their different substrate preferences. It is proposed that HMM1 is the pea HI4′OMT and that HMM2 evolved by the duplication of a gene encoding a general biosynthetic enzyme (HI4′OMT).
- Akashi, Tomoyoshi,VanEtten, Hans D.,Sawada, Yuji,Wasmann, Catherine C.,Uchiyama, Hiroshi,Ayabe, Shin-ichi
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p. 2525 - 2530
(2007/10/03)
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- COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH
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The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.
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Page/Page column 17
(2010/11/30)
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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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- An efficient 'one pot'synthesis of isoflavones
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Initial formation of deoxybenzoin 3 from phenyl acetic acid 1 and phenol 2 in the presence of BF3.Et2O followed by its treatment at room temperature with N, N'-dimethyl (chloromethylene) ammonium chloride, generated by reacting PCl5 with DMF provides a mild and efficient route for a 'one pot' synthesis of Isoflavones in high yields.
- Balasubramanian, Sreenivasan,Nair, Muraleedharan G.
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p. 469 - 484
(2007/10/03)
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- Compositions and treatments for reducing potential unwanted side effects associated with long-term administration of androgenic testosterone precursors
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A method for reducing potential adverse effects of androgenic testosterone precursors by interfering with production or action of testosterone and estrogen metabolites by nutrient combinations is described. Although androgenic testosterone precursors themselves have little or no toxicity, there is the potential for their metabolites, estradiol and dihydrotestosterone, to enhance or cause hormone-responsive illnesses such as breast or prostatic cancer, benign prostatic hyperplasia, or hirsutism or acne in women. The use of the invented nutrient combinations reduces the formation or action of estradiol and dihydrotestosterone, thereby reducing potential adverse effects from increased production of these hormones following androgenic testosterone precursor administration. This may be accomplished without negating the effects of testosterone on muscle anabolism. The nutrient combinations include androstenedione, DHEA, pregnenolone, androstenediols, norandrostenedione and norandrostenediols, and natural products which reduce estrogen effects in the estrogen-responsive tissues, and substances to reduce formation of dihydrotestosterone from testosterone in prostate tissue.
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- Process for the preparation of isoflavones
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A process for the preparation of an isoflavone from a 2'-hydroxydeoxybenzoin(I) is described. The process uses prepared N,N'-dimethyl(chloromethylene) ammonium chloride as a reactant with (I) in borontrifluoride etherate or other Lewis acid as a solvent. The isoflavones are known biologically active compounds.
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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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- Mixed Anhydride of Acetic and Formic Acids in the Synthesis of Chromones. 2. Synthesis of 3-Arylchromones
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A study was carried out on the reaction of α-substituted 2-hydroxyacetophenones eith the mixed anhydride of acetic and formic acids in the presence of bases of different strength.Chromones containing a conjugated electron-withdrawing substituent at C(3) are formed in close to quantitative yield in the presence of triethylamine.The preparation of chromones containing an unconjugated substituent under these conditions is recommended only for 5-hydroxychromones.
- Pivovarenko, V. G.,Khilya, V. P.
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p. 497 - 502
(2007/10/02)
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- Expedient Synthesis of Polyhydroxyisoflavones
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A general and direct synthesis of polyhydroxy isoflavones (3-phenyl-4H-1-benzopyran-4-ones) starting from the corresponding unprotected phenols and arylacetic acids is described.The aryl rings may carry additional alkyl, methoxy and/or halogeno groups.Intermediate polyhydroxydeoxybenzoins (1,2-diphenylethanones) can also be isolated in good yields.
- Waehaelae, Kristiina,Hase, Tapio A.
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p. 3005 - 3008
(2007/10/02)
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- Ground mixture
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A ground mixture of a poorly soluble crystalline drug and an adsorbent is remarkably improved in the rates of dissolution and adsorption of the drug.
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- EFFECTIVE SYNTHESIS OF 7-HYDROXYISOFLAVONE O-GLUCOSIDES
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An effective procedure for condensing acetobromoglucose with 2,4-dihydroxy phenyl benzyl ketones has been developed.The 2-hydroxy-4-(β-D-tetra-O-acetylglucopyranosyloxy)phenyl benzyl ketones synthesized with yields of 47-69percent have been converted under the action of ethyl orthoformate in pyridine solution into 7-hydroxyisoflavone O-glukosides and these have also been obtained by the glycosylation of 7-hydroxyisoflavone.The advantages and disadvantages of the alternative pathways of the synthesis of 7-hydroxyisoflavone O-glykosides are discussed.
- Pivovarenko, V. G.,Khilya, V. P.,Kovalev, V. N.,Vasil'ev, S. A.
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p. 432 - 438
(2007/10/02)
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- One-Pot Synthesis of Unsymmetrically Substituted 2,4-Dialkylisoflavenes
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The trimethylsilyl derivative of formonometine reacts sequentially with two different organometallic derivatives to afford regiospecifically and with good yield 2,4-dialkylisoflavenes unsymmetrically substituted.
- Alberola, Angel,Andres, Celia,Ortega, Alfonso Gonzalez,Pedrosa, Rafael,Vicente, Martina
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p. 1781 - 1783
(2007/10/02)
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