- Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives
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Thirty dihydroflavonol derivatives (D1–D30) were designed and synthesized, meanwhile the synthesized compounds were characterized on the basis of spectroscopic analyzes. Their inhibitory activity against the pro-inflammatory inducible interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophages were evaluated and showed various efficiency. Compounds D1–D30 showed no toxic effects on RAW 264.7 cells at the concentration 20 μM; among them, compounds D9, D13, and D19 exhibited best anti-inflammatory activity through decreasing IL-1β, IL-6, and TNF-α. Furthermore, their structure–activity relationships were discussed preliminarily.
- Hu, Chunling,Zhou, Zongbao,Xiang, Yuanhang,Song, Xiaoying,Wang, Hong,Tao, Kaiqi,Ye, Xiaochuan
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p. 194 - 205
(2018/04/19)
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- Production of hydroxlated flavonoids with cytochrome P450 BM3 variant F87V and their antioxidative activities
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A variant of P450 BM3 with an F87V substitution [P450 BM3 (F87V)] is a substrate-promiscuous cytochrome P450 monooxygenase. We investigated the bioconversion of various flavonoids (favanones, chalcone, and isoflavone) by using recombinant Escherichia coli cells, which expressed the gene coding for P450 BM3 (F87V), to give their corresponding hydroxylated products. Potent antioxidative activities were observed in some of the products.
- Kitamura, Emi,Otomatsu, Toshihiko,Maeda, Chiemi,Aoki, Yoko,Ota, Chihiro,Misawa, Norihiko,Shindo, Kazutoshi
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p. 1340 - 1343
(2013/07/26)
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- Hydromagnesite as an efficient recyclable heterogeneous solid base catalyst for the synthesis of flavanones, flavonols and 1,4-dihydropyridines in water
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A form of hydromagnesite (HM) with flower-like thin-sheet morphology was synthesized by an environmentally benign approach using simple conventional heating at moderate temperature without using any template in water as medium. The versatility of this HM catalyst was studied in the synthesis of flavanones, flavonols and the multicomponent synthesis of 1,4-dihydropyridines in water. The recyclability of catalyst was studied for six times and there was no appreciable loss in its catalytic activity. Copyright
- Rajesh, U. Chinna,Manohar, Sunny,Rawat, Diwan S.
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p. 3170 - 3178
(2013/12/04)
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- Oxidative rearrangement of flavanones with thallium(III) nitrate, lead tetraacetate and hypervalent iodines in trimethyl orthoformate and perchloric or sulfuric acid
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An HPLC monitoring protocol has been developed to follow the reaction of flavanone [(±)-1] with thallium(III) nitrate, lead tetracetate, phenyliodonium diacetate (PIDA) or [hydroxyl(tosyloxy)iodo]benzene in trimethyl orthoformate. Besides the major ring-c
- Nemeth, Istvan,Kiss-Szikszai, Attila,Zita Illyes, Tuende,Mandi, Attila,Komaromi, Istvan,Kurtan, Tibor,Antus, Sandor
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p. 1289 - 1296
(2013/02/23)
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- Facile epoxidation of α,β-unsaturated ketones with cyclohexylidenebishydroperoxide
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Cyclohexylidenebishydroperoxide was successfully used as the oxygen source for the oxidation of α,β-unsaturated ketones for the first time. The corresponding epoxides were obtained in excellent yields under the Weitz-Scheffer reaction conditions.
- Jakka, Kavitha,Liu, Jinyun,Zhao, Cong-Gui
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p. 1395 - 1398
(2007/10/03)
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- Synthetic studies towards the preparation of 2-benzyl-2-hydroxybenzofuran- 3(2H)-one, the prototype of naturally occurring hydrated auronols
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Various synthetic approaches were employed to prepare 2-benzyl-2- hydroxybenzofuran-3(2H)-one (8), the prototype of naturally occurring auronols. While the base-induced ring transformation of 3-hydroxyflavanone (2) as well as the hydration of 2-benzylidenebenzofuran-3(2H)-one (=aurone; 6) proved to be inappropriate, the hydrogenolytic epoxide-ring opening of 2′- phenylspiro[benzofuran-2(3H),2′-oxiran]-3-one (7), obtained from 6, represents an efficient method to afford the auronol 8.
- Loeser, Reik,Chlupacova, Marta,Marecek, Ales,Opletalova, Veronika,Guetschow, Michael
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p. 2597 - 2601
(2007/10/03)
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- Synthesis of racemic and enantiomerically enriched α- oxyfunctionalized benzocyclanones and chromanones by dimethyldioxirane and dimethyldioxirane/Mn(III) salen system
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Enolacetates of benzocyclanones and chromanones were synthesized and treated with dimethyldioxirane and the asymmetric oxidizing system dimethyldioxirane/chiral, non-racemic Mn(III) salen complex/axial ligand. The latter reagent resulted in the corresponding enantiomerically enriched cyclic α-hydroxy ketones and their acetates in moderate-to-good yields and modest enantioselectivity under mild and neutral conditions from tetralone and chromanone. On the contrary, flavanone provided poor yields due to the competitive C-H insertion at position 2. The use of R,R-Mn(III)salen catalyst induced an S absolute configuration at the position α in the whole series. Springer-Verlag 2004.
- Patonay, Tamas,Jeko, Jozsef,Kiss-Szikszai, Attila,Levai, Albert
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p. 743 - 756
(2007/10/03)
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- Flavonoid epoxides. Part 20. Some unusual reactions of dimethyldioxirane (DMD) with flavonoid compounds
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Dimethyldioxirane (DMD), generally as a solution in acetone, has proved itself to be an excellent epoxidising agent. It was observed that either the 2'-hydroxychalcone epoxide or the tans-2,3-dihydroflavonol could be obtained depending on the pH of the reaction mixture and the type of β-arene ring present in the substrate. Using this methodology trans-2,3-dihydroflavonols can be synthesised in far better yields than by the most commonly used method for their synthesis, that of the Algar-Flynn-Oyamada reaction. Treatment of both flavonol 14 and the novel isoaurone 21 with DMD gave unusual products instead of the expected epoxides, but nonetheless, an epoxide was assumed to have formed during the reaction.
- Burke, Anthony J.,O'Sullivan, W. Ivo
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p. 8491 - 8500
(2007/10/03)
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- Synthesis and cyclization of 1-(2-hydroxyphenyl)-2-propen-1-one epoxides: 3-Hydroxychromanones and -flavanones versus 2-(1-hydroxyalkyl)-3-coumaranones
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Competitive α and β cyclization of 2'-hydroxychalcone epoxides affords 2-(α-hydroxybenzyl)-3-coumaranone and/or 3-hydroxyflavanones, which depends on the conditions employed. Epoxidation of 2'-hydroxychalcones by dimethyldioxirane followed by either base- or acid-catalyzed ring closure provides a novel, general, and efficient method for the synthesis of trans-3-hydroxyflavanones, which includes also the naturally occurring derivatives. Extension of this two-step procedure to 1-(2-hydroxyphenyl)-2-alken-1-ones was also accomplished. A strong preference for α cyclization was observed in the case of β-unsubstituted or -monoalkylated α,β-enones, while both 2,2-dimethyl-3-hydroxychromanones and 2-(1-hydroxy-1-methylethyl)-3-coumaranones were obtained from the β,β-dimethylated substrates.
- Patonay, Tamas,Levai, Albert,Nemes, Csaba,Timar, Tibor,Toth, Gabor,Adam, Waldemar
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p. 5375 - 5383
(2007/10/03)
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- Dimethyldioxirane Oxidation of Titanium Enolates: Diastereoselective α-Hydroxylations
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The oxidation of titanium enolates, derived from a transmetalation of the corresponding lithium enolates with (i-PrO)3TiCl, (Et2N)3TiCl, or Cp2TiCl2, by dimethyldioxirane has been investigated.Furthermore, the diastereoselective hydroxylation of the chiral metal enolates, e.g., derived from camphor (1f), menthone (1g), flavanone (1h), and 2-benzylcyclopentanone (1i), by dimethyldioxirane has been examined.The diastereoselectivity of the oxygen transfer strongly depends on the metal partner coordinated to the enolate.The titanium enolates 4 resulted in much higher diastereoselectivities (up to 96percent de) than the corresponding sodium enolates 5 and at least as high if not higher than the silyl enol ethers 6.Moreover, the aldol reaction of ester-derived sodium enolates with acetone, the unavoidable medium for dimethyldioxirane, could be totally suppressed by the use of the chlorotitanocene enolates 4.Thus, the oxidation of chiral titanium enolates by dimethyldioxirane represents a general, convenient, effective, and chemo- and diastereoselective synthesis of α-hydroxy carbonyl compounds.
- Adam, Waldemar,Mueller, Michael,Prechtl, Frank
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p. 2358 - 2364
(2007/10/02)
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- A convenient and general synthesis of trans-3-hydroxyflavanones from chalcones by dimethyldioxirane epoxidation and subsequent base-catalyzed cyclization
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2'-Hydroxychalcone epoxides were found to give trans-3-hydroxyflavanone and 2-(α-hydroxybenzyl)-3-coumaranone under basic conditions. Epoxidation of 2'-hydroxychalcones with dimethyldioxirane followed by treatment of tetrabutylammonium hydroxide provides a convenient and general method for the synthesis of trans-3-hydroxyflavanones.
- Patonay,Toth,Adam
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p. 5055 - 5058
(2007/10/02)
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- Kinetics and Mechanism of the Cyclisation of Some 2'-Hydroxychalcone Epoxides and Subsequent Elimination Reactions of Aurone Hydrates
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Analysis of the pH-rate profile for the cyclisation of the monoanion of 2'-hydroxychalcone epoxide which gives 3-hydroxyflavanone and of some 6'-alkoxy-substituted analogues which give mostly aurone hydrate, gives rate coefficients which quantify the preference for α over β cyclisation when 6'-substituents are present.These are considered in terms of stereoelectronic factors which may be responsible for the preference.Also reported are rate coefficients for the subsequent reaction of aurone hydrates in which aurones and coumaranones are formed.
- Adams, Christopher J.,Main, Lyndsay
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p. 9929 - 9938
(2007/10/02)
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- Hypervalent Iodine Oxidation of Flavanone. Synthesis of cis- and trans-3-Hydroxyflavanones
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The synthesis of cis-3-hydroxyflavanone (3a) from flavanone (1) via acid-catalyzed hydrolysis of dimethyl acetal 4 formed by C6H5I(OAc)2-KOH/CH3OH oxidation is described.Unger more vigrous hydrolytic conditions isomerization accompanies hydrolysis of 4 wi
- Moriarty, Robert M.,Prakash, Om
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p. 151 - 153
(2007/10/02)
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- HETEROCYCLES. XIV. EFFICIENT STEREOCONTROLLED SYNTHESIS OF RACEMIC FLAVONOIDS
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Stereocontrolled synthesis of the flavonoids (2, 4 and 5) is described.Racemic taxifolin (dihydroquercetin) (14) is synthesized by application of this method.
- Takahashi, Hiroshi,Kubota, Yumiko,Miyazaki, Hiroko,Onda, Masayuki
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p. 1147 - 1153
(2007/10/02)
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- Heterocycles. XV. Enantioselective Synthesis of Chiral Flavanonols and Flavan-3,4-diols
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Chiral flavanonols and flavan-3,4-diols have been enantioselectively synthesized from the chiral epoxychalcones (-)-2a and (+)-2b, which are obtained by the asymmetric epoxidation of the chalcone 1 under phase-transfer conditions.The absolute configuratio
- Takahashi, Hiroshi,Kubota, Yumiko,Miyazaki, Hiroko,Onda, Masayuki
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p. 4852 - 4857
(2007/10/02)
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