Conformationally restricted hybrids of CP-55,940 and HHC: Stereoselective synthesis and activity

Tius, Marcus A.; Makriyannis, Alexandros; Zoua, Xiang Long; Abadji, Vasiliki

doi:10.1016/s0040-4020(01)86983-0

Cited by 32 publications

(17 citation statements)

References 18 publications

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“…This was motivated by earlier work in which we have demonstrated that the tricyclic component in this series of analogues is a very successful pharmacophore for the two known cannabinoid receptors. 21 …”

Section: Resultsmentioning

confidence: 99%

Heteroadamantyl Cannabinoids

Dixon

Sethumadhavan²,

Benneche³

et al. 2010

J. Med. Chem.

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The aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have synthesized a series of analogues in which the C3 position is substituted either directly or through a one-carbon atom linker with an adamantylamine or with an oxa- or an oxazaadamantane. The oxaadamantane pharmacophore in analogue 16 showed the best binding profile for both receptors.

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Section: Resultsmentioning

confidence: 99%

Heteroadamantyl Cannabinoids

Dixon

Sethumadhavan²,

Benneche³

et al. 2010

J. Med. Chem.

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“…Further refinement of the CC/NCC hybrids was obtained by imposing restricted rotation around this SAH pharmacophore which was accomplished through the introduction of double and triple bonds at the C2'' position of the 6β-hydroxypropyl chain (13). This promising class of compounds encompassing four asymmetric centers is amongst the most structurally complex and potent cannabinergics synthesized to date [83][84][85][86][87][88][89].…”

Section: Hybrid Cannabinoidsmentioning

confidence: 99%

CB1 Cannabinoid Receptor Ligands

Thakur¹,

Nikas²,

Makriyannis³

2005

MRMC

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The CB1 receptor is expressed in the central nervous system and numerous other tissues including heart, lung and uterus and has been recognized as an important therapeutic target for pain, appetite modulation, glaucoma, multiple sclerosis and other indications. An interesting feature of this GPCR is its ability to be activated by a number of structurally different classes of compounds, thus, raising the possibility of multiple activated forms of the receptor. Understanding of the structure-activity relationships of cannabinergic ligands has paved the road for the development of novel ligands exhibiting receptor subtype selectivity and efficacy. This review highlights the important CB1 cannabinergic ligands developed to date.

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“…The preference for the 9β relative configuration has been used for the design and synthesis of high affinity photoactivatable probes for the cannabinoid receptors (e.g. This pharmacophore is referred to as the southern aliphatic hydroxyl group (SAH) [115,142,[162][163][164][165]. 4) [117].…”

Section: A) Classical and Non-classical Cannabinoidsmentioning

confidence: 99%

Cannabinoid Receptors as Therapeutic Targets

Pavlopoulos¹,

Thakur²,

Nikas³

et al. 2006

CPD

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The cannabinoid receptors CB1 and CB2 are family A, G-protein Coupled Receptors that mediate the effects of cannabinoids, a class of compounds that are so named because the first members were isolates of the cannabis plant. In recent history, there has been much anecdotal evidence that the potent and diverse physiological responses produced by these compounds can be turned to therapeutic benefit for a wide variety of maladies. The remarkable abundance of cannabinoid receptors and the discovery of several endogenous ligands along with enzyme and transporter proteins for which they are substrates, suggests that an endogenous cannabinoid neuromodulatory system is an important mediator of biological function. For these reasons CB1 and CB2 receptors are attractive targets for the design of therapeutic ligands. The action of these receptors, however, may also be modulated by manipulating the enzymes and membrane transporters that regulate the endogenous ligands. Despite the range of physiological processes and activities that are mediated by cannabinoid receptors, it is clear that it is possible to produce ligands that result in differential responses. In this paper, we review the pharmacophoric elements that lead to these differential responses and in order to discuss them in context we present an overview of structural aspects governing cannabinoid receptor function, the cannabinergic system and its physiological functions.

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Conformationally restricted hybrids of CP-55,940 and HHC: Stereoselective synthesis and activity

Cited by 32 publications

References 18 publications

Heteroadamantyl Cannabinoids

Heteroadamantyl Cannabinoids

CB1 Cannabinoid Receptor Ligands

Cannabinoid Receptors as Therapeutic Targets

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