1621-55-2Relevant academic research and scientific papers
Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives
Hu, Chunling,Zhou, Zongbao,Xiang, Yuanhang,Song, Xiaoying,Wang, Hong,Tao, Kaiqi,Ye, Xiaochuan
, p. 194 - 205 (2018/04/19)
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.
Production of hydroxlated flavonoids with cytochrome P450 BM3 variant F87V and their antioxidative activities
Kitamura, Emi,Otomatsu, Toshihiko,Maeda, Chiemi,Aoki, Yoko,Ota, Chihiro,Misawa, Norihiko,Shindo, Kazutoshi
, p. 1340 - 1343 (2013/07/26)
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.
Hydromagnesite as an efficient recyclable heterogeneous solid base catalyst for the synthesis of flavanones, flavonols and 1,4-dihydropyridines in water
Rajesh, U. Chinna,Manohar, Sunny,Rawat, Diwan S.
, p. 3170 - 3178 (2013/12/04)
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
Oxidative rearrangement of flavanones with thallium(III) nitrate, lead tetraacetate and hypervalent iodines in trimethyl orthoformate and perchloric or sulfuric acid
Nemeth, Istvan,Kiss-Szikszai, Attila,Zita Illyes, Tuende,Mandi, Attila,Komaromi, Istvan,Kurtan, Tibor,Antus, Sandor
, p. 1289 - 1296 (2013/02/23)
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
Facile epoxidation of α,β-unsaturated ketones with cyclohexylidenebishydroperoxide
Jakka, Kavitha,Liu, Jinyun,Zhao, Cong-Gui
, p. 1395 - 1398 (2007/10/03)
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.
Synthesis of racemic and enantiomerically enriched α- oxyfunctionalized benzocyclanones and chromanones by dimethyldioxirane and dimethyldioxirane/Mn(III) salen system
Patonay, Tamas,Jeko, Jozsef,Kiss-Szikszai, Attila,Levai, Albert
, p. 743 - 756 (2007/10/03)
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.
Synthetic studies towards the preparation of 2-benzyl-2-hydroxybenzofuran- 3(2H)-one, the prototype of naturally occurring hydrated auronols
Loeser, Reik,Chlupacova, Marta,Marecek, Ales,Opletalova, Veronika,Guetschow, Michael
, p. 2597 - 2601 (2007/10/03)
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.
Flavonoid epoxides. Part 20. Some unusual reactions of dimethyldioxirane (DMD) with flavonoid compounds
Burke, Anthony J.,O'Sullivan, W. Ivo
, p. 8491 - 8500 (2007/10/03)
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.
Synthesis and cyclization of 1-(2-hydroxyphenyl)-2-propen-1-one epoxides: 3-Hydroxychromanones and -flavanones versus 2-(1-hydroxyalkyl)-3-coumaranones
Patonay, Tamas,Levai, Albert,Nemes, Csaba,Timar, Tibor,Toth, Gabor,Adam, Waldemar
, p. 5375 - 5383 (2007/10/03)
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.
Dimethyldioxirane Oxidation of Titanium Enolates: Diastereoselective α-Hydroxylations
Adam, Waldemar,Mueller, Michael,Prechtl, Frank
, p. 2358 - 2364 (2007/10/02)
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.
