Academic literature on the topic 'Aza-lignans'

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Journal articles on the topic "Aza-lignans"

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Florent, Jean-Claude, Emmanuel Bertounesque, Matthieu Dorbec, Claude Monneret, and Marie-Noëlle Rager. "Synthesis of γ-Lactam Lignans via Aza-Michael Addition." Synlett, no. 4 (2006): 0591–94. http://dx.doi.org/10.1055/s-2006-932485.

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Barker, David, Benjamin Dickson, Nora Dittrich, and Claire E. Rye. "An acyl-Claisen approach to the synthesis of lignans and substituted pyrroles." Pure and Applied Chemistry 84, no. 7 (March 25, 2012): 1557–65. http://dx.doi.org/10.1351/pac-con-11-09-27.

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The acyl-Claisen rearrangement, also called a zwitterionic aza-Claisen rearrangement, allows for the synthesis of 2,3-syn-substituted morpholine pent-4-eneamides with high levels of diastereoselectivity. A wide variety of alkyl and aryl substituents can be introduced with yields highly dependent on the stoichiometry of the Lewis acid catalyst. The use of these morpholine amides in the synthesis of the tetrasubstituted tetrahydrofuran lignans fragransin A2, talaumidin, and galbelgin is summarized. The conversion of the Claisen-derived amides into aryl tetraline and 1,1-diarylbutanol lignans via alteration of the protecting groups is also described. Nucleophilic addition of an organometallic reagent to the morpholine amide followed by Wacker oxidation of the alkene gives highly substituted 1,4-diketones, which can be easily converted into fully substituted pyrroles.
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Ourhzif, El‐Mahdi, Arnaud Pâris, Isabelle Abrunhosa‐Thomas, El Mostafa Ketatni, Pierre Chalard, Mostafa Khouili, Richard Daniellou, Yves Troin, and Mohamed Akssira. "Design, synthesis, and evaluation of cytotoxic activities of arylnaphthalene lignans and aza‐analogs." Archiv der Pharmazie 354, no. 6 (February 15, 2021): 2000479. http://dx.doi.org/10.1002/ardp.202000479.

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Hitotsuyanagi, Yukio, Masatsugu Kobayashi, Masamoto Fukuyo, Koichi Takeya, and Hideji Itokawa. "A facile synthesis of the 4-aza-analogs of 1-arylnaphthalene lignans chinensin, justicidin B, and Taiwanin C." Tetrahedron Letters 38, no. 48 (December 1997): 8295–96. http://dx.doi.org/10.1016/s0040-4039(97)10204-0.

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HITOTSUYANAGI, Y., M. KOBAYASHI, M. FUKUYO, K. TAKEYA, and H. ITOKAWA. "ChemInform Abstract: A Facile Synthesis of the 4-Aza-Analogues of 1-Arylnaphthalene Lignans Chinensin, Justicidin B, and Taiwanin C." ChemInform 29, no. 7 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199807171.

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Dorbec, Matthieu, Jean-Claude Florent, Claude Monneret, Marie-Noelle Rager, and Emmanuel Bertounesque. "Synthesis of γ-Lactam Lignans via Aza-Michael Addition." ChemInform 37, no. 28 (July 11, 2006). http://dx.doi.org/10.1002/chin.200628207.

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Xiang, Jia-Chen, Cédric Fung, Qian Wang, and Jieping Zhu. "Taming the radical cation intermediate enabled one-step access to structurally diverse lignans." Nature Communications 13, no. 1 (June 16, 2022). http://dx.doi.org/10.1038/s41467-022-31000-4.

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AbstractLignans, in spite of their structural diversity, are all biosynthetically derived from coniferyl alcohol. We report herein a divergent synthesis of lignans from biomass-derived monolignols in a short synthetic sequence. Blue LED irradiation of a dichloromethane solution of dicinnamyl ether derivatives in the presence of Cu(TFA)2, an alcohol (2.0 equiv) and a catalytic amount of Fukuzumi’s salt affords the C7-alkoxylated aryltetralin cyclic ethers. Increasing the amount of alcohol under otherwise identical conditions diverts the reaction course to furnish the C7,C7’-dialkoxylated dibenzyltetrahydrofurans, while replacing Cu(TFA)2 with diphenyl disulfide (PhSSPh) provides selectively the C7-monoalkoxylated dibenzyltetrahydrofurans. Aza-, thia- and carba-analogues of lignans are equally accessible by simply changing the tethering atom of the allylic alcohols. Concise total syntheses of aglacins A, E, F, brassilignan, and dehydrodimethylconidendrin are documented featuring these transformations.
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Dissertations / Theses on the topic "Aza-lignans"

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Ourhzif, El-Mahdi. "Synthèse et évaluation pharmacologique de composés originaux de la famille des méthoxynaphtalènes et lignanes arylnaphtalènes à visée antitumorale." Electronic Thesis or Diss., Université Clermont Auvergne (2021-...), 2022. http://www.theses.fr/2022UCFAC016.

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Le cancer du sein est la tumeur maligne la plus fréquente chez les femmes, il reste le premier en termes d’incidence (2,1 millions de nouveaux cas dans le monde en 2018) et de phénomènes de résistance des cellules cancéreuses aux différents traitements sont apparue. En raison de son impact majeur sur la population, cette maladie représente un problème de santé publique critique qui nécessite des recherches supplémentaires aux niveaux moléculaires afin de définir son traitement spécifique. Le règne végétal reste une source primordiale pour de nombreux chercheurs afin de trouver de nouvelles molécules biologiquement actives, pouvant amener à la découverte de principes actifs potentiellement intéressants sur le plan thérapeutique. Les principes actifs sont directement isolés des extraits des plantes, ou obtenus par hémisynthèse à partir des molécules d’extraction. C’est dans cette démarche que les travaux réalisés par notre groupe de recherche, dans le domaine de l’extraction et la synthèse de substances antalgiques et anticancéreuses, à partir des plantes utilisées dans la pharmacopée traditionnelle, nous ont conduits à envisager des pharmacomodulations en série sur des analogues de la « Guieranone A », molécule naturelle isolée à partir des feuilles de Guiera senegalensis plante largement utilisée en médecine traditionnelle africaine pour ces propriétés thérapeutiques et qui possède des activités antiprolifératives remarquables sur différents lignées tumorales et en particulier sur le cancer du sein (lignée hormono-dépendante MCF-7, CI50 =3,42 ±0,090 µM ). Nous avons donc développé une approche synthétique permettant la préparation des méthoxynaphtalènes et de méthoxynaphtoquinones. Cette approche utilise comme produit de départ le 3,4-diméthoxy benzaldehyde et met en jeu des réactions de type Stobbe et Wittig-Horner-Emmons. Les réactions de synthèses développées sur cette base, ainsi que les molécules préparées, ont permis de synthétiser également des lignanes et des aza-lignanes, composés d’intérêt biologiques ou / et pharmacologiques très représentés dans de nombreuses plantes aromatiques et médicinales (PAM), du genre Justicia et Vitex. Notre méthode de synthèse a permis la préparation avec de bons rendements, des produits naturels et ses analogues (Justicidine C, Cilinaphthalide B, Méthoxy-vitedoamine A), via une réaction de chloroformylaion suivie d’une réaction de couplage de Suzuki-Miyaura
Breast cancer is the most common malignant tumor in women, and the first in terms of incidence (2.1 million new cases worldwide in 2018). An increasing problem is the resistance of some cancer cells to different treatments. Due to its major impact on the population, this disease represents a critical public health problem that requires additional research at the molecular level in order to define specific therapies. The plant kingdom remains an essential source for many researchers in order to find new biologically active molecules, which can lead to the discovery of active ingredients. It is in this approach that the work carried out by our research group, in the field of the extraction and synthesis of analgesic and anticancer substances from plants used in traditional pharmacopoeia, led us to consider serial pharmacomodulations on analogues of « Guieranone A », a natural molecule isolated from the leaves of the Guiera senegalensis plant which is widely used in traditional African medicine for its therapeutic properties and which has remarkable antiproliferative activities on various tumor lines and in particular on breast cancer (MCF-7 hormone-dependent line, IC50 = 3.42 ± 0.090 µM). We have therefore developed a synthetic approach using 3,4-dimethoxy benzaldehyde as a starting material and involving Stobbe and Wittig-Horner-Emmons reactions. The synthetic reactions developed on this basis, as well as the molecules prepared, have opened a synthetic route to lignans and aza-lignans, compounds of biological and / or pharmacological interest well represented in many aromatic and medicinal plants (AMP), of the genus Justicia and Vitex. By this way, Justicidin C, Cilinaphthalide B, and Methoxy-vitedoamine A were prepared via a chloroformylation reaction followed by a Suzuki-Miyaura coupling reaction
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