58545-48-5Relevant academic research and scientific papers
Design of Negative and Positive Allosteric Modulators of the Cannabinoid CB2Receptor Derived from the Natural Product Cannabidiol
Navarro, Gemma,Gonzalez, Angel,Sánchez-Morales, Adrià,Casajuana-Martin, Nil,Gómez-Ventura, Marc,Cordomí, Arnau,Busqué, Félix,Alibés, Ramon,Pardo, Leonardo,Franco, Rafael
, p. 9354 - 9364 (2021/07/19)
Cannabidiol (CBD), the second most abundant of the active compounds found in the Cannabis sativa plant, is of increasing interest because it is approved for human use and is neither euphorizing nor addictive. Here, we design and synthesize novel compounds taking into account that CBD is both a partial agonist, when it binds to the orthosteric site, and a negative allosteric modulator, when it binds to the allosteric site of the cannabinoid CB2 receptor. Molecular dynamic simulations and site-directed mutagenesis studies have identified the allosteric site near the receptor entrance. This knowledge has permitted to perform structure-guided design of negative and positive allosteric modulators of the CB2 receptor with potential therapeutic utility.
Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
Tao, Lei,Guo, Xueying,Li, Jie,Li, Ruoling,Lin, Zhenyang,Zhao, Wanxiang
supporting information, p. 18118 - 18127 (2020/11/26)
The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.
Solid-Phase Reactive Chromatography (SPRC): A new methodology for wittig and horner-emmons reactions on a column under microwave irradiation
Dakdouki, Saada C.,Villemin, Didier,Bar, Nathalie
experimental part, p. 333 - 337 (2010/04/02)
A new methodology named solid-phase reactive chromatography (SPRC), which combines reaction, separation, and purification into a single unit for the preparation of small samples, is described. This method was illustrated in the synthesis of some natural bioactive compounds, namely, methoxylated analogues of resveratrol, alkylresorcinols, and 5-aryl-2,4-pentadienoates, over a column of alumina-KF under microwave irradiation by using the Wittig and HornerEmmons reactions. This approach permitted the preparation of the target olefins with high purity and good to excellent yields in short reaction times.
The Diels-Alder approach towards cannabinoids
Lesch, Bernhard,Toraeng, Jakob,Nieger, Martin,Braese, Stefan
, p. 1888 - 1900 (2007/10/03)
Starting from the efficient synthesis of benzopyrans by base-catalyzed condensation reactions between substituted 2-hydroxybenzaldehydes and α,β-unsaturated aldehydes, thermal, Lewis acid catalyzed and enantioselective organo-promoted Diels-Alder reactions towards the tricyclic cannabinoid system are presented. The procedures are exemplified by the synthesis of a pentacycle and various tricycles respectively, in up to 95% enantiomeric excess and provide a versatile entry to this group of natural products with tetrahydrocannabinol (THC) being the most prominent one. Most published strategies are based on the formation of the tricyclic system by condensation between readily available phenols and monoterpenes, whereas we present a novel approach to cannabinoid derivatives based on a modular synthesis. Georg Thieme Verlag Stuttgart.
Synthesis of both enantiomers of hiburipyranone
Uchida, Kanako,Watanabe, Hidenori,Kitahara, Takeshi
, p. 8975 - 8984 (2007/10/03)
Both enentiomers of hiburipyranone, a cytotoxic metabolite of marine sponge, was synthesized employing Sharpless' asymmetric dihydroxylation as a key step and absolute configuration of the natural compound at C-3 position was determined to be R.
5-Alkylresorcinols from Hakea trifurcata that cleave DNA
Lytollis, William,Scannell, Ralph T.,An, Haoyun,Murty,Reddy, K. Sambi,Barr, John R.,Hecht, Sidney M.
, p. 12683 - 12690 (2007/10/03)
A dichloromethane extract of Hakea trifurcata that mediated relaxation of ?X174 replicative form DNA at micromolar concentrations in the presence of Cu2+ was resolved into six active components by bioassay-guided fractionation. Five of the acti
