- 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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- Synthesis and biological evaluation of pyranoisoflavone derivatives as anti-inflammatory agents
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In this paper, barbigerone (1a) and its twenty-seven related structural analogues were synthesized via complementary synthetic routes and their anti-inflammatory effects on the expression of TNF-α in LPS-stimulated splenocytes were evaluated. Among these compounds, 1a, 1d, 1f and 1g were found to remarkably inhibit TNF-α production. Furthermore, 1g showed the most potent and dose-dependent manner inhibitory effect on TNF-α release, with better IC50 value (3.58 μM) than barbigerone (8.46 μM). Oral administration of 1g at 20 mg/kg/day for two weeks obviously demonstrated protective effect in adjuvant-induced arthritis models as evaluated by clinical score of paws, and histological examination of joint tissues from rats. Mechanism studies on mRNA and protein level suggested that 1g inhibited the TNF-α production via depressing TNF-α converting enzyme (TACE) mRNA expression. In conclusion, these data show 1g with potential therapeutic effects as an anti-inflammatory agent.
- Wei, Zhe,Yang, Youzhe,Xie, Caifeng,Li, Chunyan,Wang, Guangcheng,Ma, Liang,Xiang, Mingli,Sun, Jian,Wei, Yuquan,Chen, Lijuan
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p. 172 - 183
(2014/07/21)
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- The synthesis and evaluation of flavone and isoflavone chimeras of novobiocin and derrubone
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The natural products novobiocin and derrubone have both demonstrated Hsp90 inhibition and structure-activity relationships have been established for each scaffold. Given these compounds share several key structural features, we hypothesized that incorporation of elements from each could provide insight to structural features important for Hsp90 inhibition. Thus, chimeric analogues of novobiocin and derrubone were constructed and evaluated. These studies confirmed that the functionality present at the 3-position of the isoflavone plays a critical role in determining Hsp90 inhibition and suggests that the bicyclic ring system present in both novobiocin and derrubone do not share similar modes of binding.
- Mays, Jared R.,Hill, Stephanie A.,Moyers, Justin T.,Blagg, Brian S.J.
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experimental part
p. 249 - 266
(2010/04/05)
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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; 66
(2009/04/25)
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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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- FLAVONOIDS OF Thermopsis alterniflora. CROTONOYLTHERMOPSOSIDE AND CROTONOYLCOSMOSIIN - NEW ACYLATED FLAVONE GLYCOSIDES
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From the epigeal part of Thermopsis alterniflora Rgl. et Schmalh. (Fabaceae), in addition to formononetin, ononin, cynaroside, and rothindin, two new acylated flavone glycosides have been isolated and, on the basis of chemical transformations and spectral characteristics, their structures have been established as 4',5,7-trihydroxy-3'-methoxyflavone 7-O-(6"-O-crotonoyl-β-D-glucopyranoside) and 4',5,7-trihydroxyflavone 7-O-(6"-O-crotonoyl-β-D-glucopyranoside).
- Yuldashev, M. P.,Batirov, E. Kh.,Vdovin, A. D.,Malikov, V. M.,Yagudaev, M. R.
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p. 303 - 308
(2007/10/02)
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- Total Synthesis of Isoflavones: Jamaicin, Calopogonium Isoflavone-B, Pseudobaptigenin, and Maxima Substance-B. Friedel-Crafts Acylation Reactions with Acid-Sensitive Substrates
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The Friedel-Crafts acylation reaction was studied on several acid-sensitive substrates.Under the proper conditions of varying Lewis acids, solvents, and reaction temperatures, the acylation indeed took place, thus obviating the necessity for functional group protection-deprotection sequences.By use of these procedures, the naturally occuring isoflavones jamaicin (1), calopogonium isoflavone-B (2), maxima substance-B (30), and pseudobaptigenin (31) were synthesized and characterized.
- Schuda, Paul Francis,Price, William A.
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p. 1972 - 1979
(2007/10/02)
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- HYDROBORATIONS: NEW SYNTHESIS OF PSEUDO-BAPTIGENIN, O-METHYL PSEUDO-BAPTIGENIN AND CABREUVIN.
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Application of hydroboration followed by chromic acid oxydation to 4-hydroxy 7-methoxy(3',4'-methylenedioxyphenyl) coumarin and 4-hydroxy 7-benzyloxy 3-(3',4'-methylenedioxyphenyl) coumarin forms the corresponding isoflavanones which are dehydrogenated into isoflavones.
- Kirkiacharian, B. Serge,Brion, Jean-Daniel,Gomis, Michel,Reynaud, Pierre
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p. 1929 - 1934
(2007/10/02)
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