The Total Synthesis of Cannabinoids

Razdan, Raj K.

doi:10.1002/9780470129678.ch2

Cited by 39 publications

(23 citation statements)

References 148 publications

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“…Hence, this class includes the natural product (-)-Á 9 -THC, the more stable and nearly equiactive isomer (-)-Á 8 -THC, other active constituents of the plant such as the CBN analogs mentioned above, cannabidiol (CBD) etc., as well as their synthetic analogs especially the Á 6a,10a analogs developed by Adams and Todd. Although several synthetic strategies have been developed for the synthesis of analogs and metabolites in the Á 9 -THC series [7], most of the SAR studies in the cannabinoid field in the past several years have been carried out in the Á 8 -THC series, dictated mainly by ease of synthesis and the fact that the pharmacological profile of Á 8 -THC is very similar to Á 9 -THC, both in potency and activity.…”

Section: Introductionmentioning

confidence: 99%

Structure–Activity Relationships of Classical Cannabinoids

Razdan

2009

The Cannabinoid Receptors

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In this chapter an overview of the more recent developments in the structure-activity relationships (SARs) of classical cannabinoids is discussed, especially the profound pharmacological effects produced by various chemical entities in the side chain at C-3, the hydroxyl at C-1, C-11, and hydroxyalkyl chains at C-6. Also cardiovascular studies point to the presence of a novel cannabinoid subtype receptor and the antagonist activity of cannabidiol has opened up new areas for research. Ligands, which had either a unique pharmacological profile, were potent agonists, partial agonists/antagonists, or were CB2 selective, were identified, generating leads with the potential to be drugs in the treatment of various diseases.

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Section: Introductionmentioning

confidence: 99%

Structure–Activity Relationships of Classical Cannabinoids

Razdan

2009

The Cannabinoid Receptors

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“…47 CBC is the simplest natural phytocannabinoid to obtain by synthesis, being available, apart from CBG by oxidative dehydrogenation, also from the one step condensation of citral and olivetol (see Section 4.1.5 for a discussion on the mechanism of the reaction). 65 CBC is stable, and has been detected in centuryold historical samples of cannabis. 31 As with CBG, diversity in the derivatives of CBC is associated to oxidation of the prenyl group and the aromatic ring, with the hydroquinol hydroxylation pattern being stabilized by acetylation.…”

Section: Alkyl Phytocannabinoidsmentioning

confidence: 99%

“…74 This compound showed only negligible affinity for CB 1 and CB 2 , not unlike CBD. 74 Despite the structural similarity between CBD and D 9 -THC, the two compounds show a distinct biological prole, and, even though CBD can be electrophilically cyclized to D 9 -THC by treatment with acids, 65 the two compounds are the result of independent oxidative cyclizations of their common precursor CBGA, and are not interconverted in cannabis tissues. 29 D 9 -THC and CBD have also quite different oxidative stability.…”

Section: Alkyl Phytocannabinoidsmentioning

confidence: 99%

Phytocannabinoids: a unified critical inventory

et al. 2016

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Covering up to January 2016Cannabis sativa L. is a prolific, but not exclusive, producer of a diverse group of isoprenylated resorcinyl polyketides collectively known as phytocannabinoids. The modular nature of the pathways that merge into the phytocannabinoid chemotype translates in differences in the nature of the resorcinyl side-chain and the degree of oligomerization of the isoprenyl residue, making the definition of phytocannabinoid elusive from a structural standpoint. A biogenetic definition is therefore proposed, splitting the phytocannabinoid chemotype into an alkyl- and a β-aralklyl version, and discussing the relationships between phytocannabinoids from different sources (higher plants, liverworts, fungi). The startling diversity of cannabis phytocannabinoids might be, at least in part, the result of non-enzymatic transformations induced by heat, light, and atmospheric oxygen on a limited set of major constituents (CBG, CBD, Δ-THC and CBC and their corresponding acidic versions), whose degradation is detailed to emphasize this possibility. The diversity of metabotropic (cannabinoid receptors), ionotropic (thermos-TRPs), and transcription factors (PPARs) targeted by phytocannabinoids is discussed. The integrated inventory of these compounds and their biological macromolecular end-points highlights the opportunities that phytocannabinoids offer to access desirable drug-like space beyond the one associated to the narcotic target CB.

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“…The eventual stereogenic C-6a thereby retains its configuration in the final product. [134] Through the choice of the terpenoid building block and the reaction conditions, it is possible to influence the position of the double bond, at C-8 or C-9.…”

Section: Chemical Synthesesmentioning

confidence: 99%

Pharmaceuticals

Schaefer

2014

Natural Products in the Chemical Industry

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A boy who is born in Germany today has a probable life expectancy of around 77 years, and a girl one of 82 years -twice as long as in the year 1880. This increase is a consequence of both, better living circumstances -working conditions, food, clothing, housing -, and also a result of more comprehensive medical care. Thus, a whole range of infectious diseases has been wiped out, or brought at least under control, and the mortality rate for civilisation-and age-related diseases has dropped. Vaccinations and drugs play a key role in this outcome. The 20th century is characterised especially by the worldwide blossoming of the pharmaceutical industry. More and more, the targeted search for and development of new drugs have replaced serendipitous discoveries (Fig. 5.1). Pharmaceuticals of the last century.

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The Total Synthesis of Cannabinoids

Cited by 39 publications

References 148 publications

Structure–Activity Relationships of Classical Cannabinoids

Structure–Activity Relationships of Classical Cannabinoids

Phytocannabinoids: a unified critical inventory

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