68415-05-4Relevant academic research and scientific papers
Aged red wine pigments as a source of inspiration for organic synthesis - The cases of the color-stable pyranoflavylium and flavylium-(4→8)-flavan chromophores
Chassaing, Stefan,Isorez-Mahler, Géraldine,Kueny-Stotz, Marie,Brouillard, Raymond
, p. 3066 - 3078 (2015/05/04)
Two flavylium-based chromophores peculiar to aged red wine pigments are investigated from a synthetic viewpoint. The condensation between easy-to-prepare 5-hydroxy-4-methylflavylium salts and aldehydes, giving birth to color-stable pyranoflavylium pigments, further proves efficient and wide in scope. A set of some twenty structurally-related flavylium-based pigments has been prepared and structure:color relationships are discussed. Furthermore, the synthesis of the flavylium-(4→8)-flavan chromophore is achieved via a novel three-step sequence. The elaborated sequence starts with an iodine-magnesium exchange from an 8-iodinated flavan, thus generating a magnesiated species that then smoothly reacts with a flavone to furnish an adduct, that finally leads to the expected chromophore via dehydration.
Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever
Carre?o Otero, Aurora L.,Vargas Méndez, Leonor Y.,Duque L., Jonny E.,Kouznetsov, Vladimir V.
, p. 392 - 400 (2014/04/17)
Girgensohnine alkaloid was used as a natural model in the design and generation of new alkaloid-like α-aminonitrile series that was completed by the use of SSA-catalyzed Strecker reaction between commercial and inexpensive substituted benzaldehydes, piperidine (pyrrolidine, morpholine and N-methylpiperazine) and acetone cyanohydrin. Calculated ADMETox parameters of the designed analogs revealed their good pharmacokinetic profiles indicating lipophilic characteristics. In vitro AChE enzyme test showed that obtained α-aminonitriles could be considered as AChEIs with micromolar IC 50 values ranging from 42.0 to 478.0 μM (10.3-124.0 μg/mL). Among this series, the best AChE inhibitor was the pyrrolidine α-aminonitrile 3 (IC50 = 42 μM), followed by the piperidine α-aminonitriles 2 and 6 (IC50 = 45 μM and IC50 = 51 μM, respectively), and the compound 7 (IC50 = 51 μM). In vivo insecticidal activity of more active AChEIs against Aedes aegypti larvae was also performed showing a good larvicidal activity at concentrations less than 140 ppm, highlighting products 2 and 7 that could serve as lead compounds to develop new potent and selective insecticides.
An asymmetric synthesis of (-)-deoxypodophyllotoxin
Bogucki,Charlton
, p. 588 - 593 (2007/10/02)
A Diels-Alder cycloaddition between the fumarate of methyl (S)-mandelate (22) and α-hydroxy-α-aryl-o-quinodimethane 21 produces an endo cycloadduct (23) in 58% yield. The preparation of the precursor to o-quinodimethane 21 and the conversion of cycloadduct 23 to optically pure (-)-deoxypodophyllotoxin (1) is described.
Substituted phenyl-1,2,4-triazolo[2,3-b]pyridazin-3(2H)ones as anti-asthma agents
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, (2008/06/13)
Substituted phenyl-1,2,4-triazolo[4,3-b]pyridazin-3(2H)-ones, useful as anti-asthma agents.
