51768-57-1Relevant academic research and scientific papers
A Novel and Practical Continuous Flow Chemical Synthesis of Cannabidiol (CBD) and its CBDV and CBDB Analogues
Chiurchiù, Elena,Sampaolesi, Susanna,Allegrini, Pietro,Ciceri, Daniele,Ballini, Roberto,Palmieri, Alessandro
, p. 1286 - 1289 (2021/02/05)
Cannabidiol is one of the main non-psychoactive cannabinoids present in Cannabis sativa and, in the last decade, it is gaining great interest among the scientific community for its pharmaceutical, nutraceutical, and cosmetic applications. Herein, we report the first continuous flow chemical synthesis of cannabidiol (CBD) and its analogues cannabidivarin (CBDV) and cannabidibutol (CBDB). This approach permits to synthesize products in very good yields (55–59 %), limiting the formation of psychoactive and illegal cannabinoids such as tetrahydrocannabinol (THC).
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.
Efficient Pd-Catalyzed Direct Coupling of Aryl Chlorides with Alkyllithium Reagents
Dilchert, Katharina,Gessner, Viktoria H.,Gro?johann, Angela,Rodstein, Ilja,Scherpf, Thorsten,Steinert, Henning,Tappen, Jens
supporting information, p. 20596 - 20603 (2020/09/09)
Organolithium compounds are amongst the most important organometallic reagents and frequently used in difficult metallation reactions. However, their direct use in the formation of C?C bonds is less established. Although remarkable advances in the coupling of aryllithium compounds have been achieved, Csp2?Csp3 coupling reactions are very limited. Herein, we report the first general protocol for the coupling or aryl chlorides with alkyllithium reagents. Palladium catalysts based on ylide-substituted phosphines (YPhos) were found to be excellently suited for this transformation giving high selectivities at room temperature with a variety of aryl chlorides without the need for an additional transmetallation reagent. This is demonstrated in gram-scale synthesis including building blocks for materials chemistry and pharmaceutical industry. Furthermore, the direct coupling of aryllithiums as well as Grignard reagents with aryl chlorides was also easily accomplished at room temperature.
Preparation of 2,2-dimethylchroman-4-ones from 5-alkyl-substituted resorcinols: Microwave-assisted synthesis and theoretical calculations
Morales, Paula,Azofra, Luis Miguel,Cumella, Jose,Hernandez-Folgado, Laura,Roldan, Maria,Alkorta, Ibon,Jagerovic, Nadine
, p. 319 - 332 (2014/03/21)
The influence of different 5-alkyl-substituted resorcinols on the formation of 2,2-dimethylchroman- 4-ones is examined experimentally and theoretically. Structures are fully assigned by means of experimental and theoretical 13C and 1H NMR chemical shifts.
PHENYL-UREA AND PHENYL-CARBAMATE DERIVATIVES AS INHIBITORS OF PROTEIN AGGREGATION
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, (2013/10/21)
The present invention relates to certain phenyl-urea and phenyl-carbamate derivatives, pharmaceutical compositions containing them, and methods of using them, including methods for preventing, reversing, slowing, or inhibiting protein aggregation, and methods of treating diseases that are associated with protein aggregation, including neurodegenerative diseases such as Parkinson's disease, Alzheimer's disease, Lewy body disease, and multiple system atrophy.
Iron-catalysed, hydride-mediated reductive cross-coupling of vinyl halides and Grignard reagents
Le Bailly, Bryden A. F.,Greenhalgh, Mark D.,Thomas, Stephen P.
supporting information; experimental part, p. 1580 - 1582 (2012/03/26)
An iron-catalysed, hydride-mediated reductive cross-coupling reaction has been developed for the preparation of alkanes. Using a bench-stable iron(ii) pre-catalyst, reductive cross-coupling of vinyl iodides, bromides and chlorides with aryl- and alkyl Grignard reagents successfully gave the products of formal sp3-sp3 cross-coupling reactions.
Synthesis of chiloglottones - Semiochemicals from sexually deceptive orchids and their pollinators
Poldy, Jacqueline,Peakall, Rod,Barrow, Russell Allan
supporting information; experimental part, p. 4296 - 4300 (2009/12/06)
A five-step synthesis of monoalkyl- and 2,5-dialkyl-1,3-cyclohexanediones (1) is described via a sequence involving sequential Birch reductions and alkylations from the readily accessible and inexpensive starting material, 3,5-dimethoxybenzoic acid. Two approaches were considered in which alkylation at C-2 occurs either prior or subsequent to the proposed reduction. The successful route, in which Birch reduction of a 3-alkyl resorcinol derivative (3) precedes alkylation was applied in the synthesis of chiloglottone 1 (1dc), in 58% overall yield. Chiloglottone 1 is a member of a new class of natural products, representing a known sex pheromone of the thynnine wasp Neozeleboria cryptoides and pollinator attractant in the Australian sexually deceptive orchid genus Chiloglottis. The synthetic homologues were assessed for their biological activity via electroantennographic detection.
Pd-C-induced catalytic transfer hydrogenation with triethylsilane
Mandal, Pijus K.,McMurray, John S.
, p. 6599 - 6601 (2008/02/10)
(Chemical Equation Presented) In situ generation of molecular hydrogen by addition of triethylsilane to palladium-charcoal catalyst results in rapid and efficient reduction of multiple bonds, azides, imines, and nitro groups, as well as benzyl group and allyl group deprotection under mild, neutral conditions.
BIOLOGICALLY ACTIVE PHENOLIC METABOLITES OF A VERTICICLADIELLA SPECIES
Ayer, William A.,Browne, Lois M.,Lovell, Sarah H.
, p. 2267 - 2272 (2007/10/02)
The metabolites produced when a Verticicladiella species (Canadian Forestry Service strain C728), the causative agent of the black stain root disease of many conifers, is grown in liquid culture have been investigated.Orcinol, orcinol monomethyl ether, 1,3,6,8-tetrahydroxyanthraquinone, and the α-L-rhamnopyranosides of orcinol and orcinol methyl ether have been isolated and indentified.Orcinol methyl ether and its rhamnoside both show antibacterial activity and orcinol methyl ether also inhibits the growth of pine germlings.The general antibacterial activity of 5-alkylresorcinols and their monomethyl ethers is reported.-Key Word Index-Verticicladiella sp.; Deuteromycontina; blue-stain fungus; phytotoxin; phenols; methylorcinol rhamnoside; phenol monomethyl ethers; antiseptics.
