Development of agonists, partial agonists and antagonists in the Delta(8)-tetrahydrocannabinol series

P J  Crocker; B  Saha; W J  Ryan; J L  Wiley; B R  Martin; R A  Ross; R G  Pertwee; R K  Razdan

doi:10.1016/S0040-4020(99)00849-2

Development of agonists, partial agonists and antagonists in the Delta(8)-tetrahydrocannabinol series

P J Crocker, B Saha, W J Ryan, J L Wiley, B R Martin, R A Ross, R G Pertwee, R K Razdan

Medical Sciences

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19 Citations (Scopus)

Abstract

Synthetic sequences were developed (Schemes 1 to 6) for the syntheses of various Delta(8)-THC analogs with either a rigid acetylenic linkage or a cis-double bond in different positions in the side chain. Various alkyne and cis-ene-Delta(8)-THC analogs were also synthesized carrying a functional group such as a cyano, isothiocyano, azido, amino, nitro, bromo, hydroxy, fluoro and a methoxy group at the chain terminal. The in vitro and in vivo pharmacology of these unique analogs have provided several ligands which are partial agonists or antagonists of the cannabinoid receptor CB1. The 2'-position in the side chain was found to be optimum for activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	13907-13926
Number of pages	20
Journal	Tetrahedron
Volume	55
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4020(99)00849-2
Publication status	Published - 3 Dec 1999

Keywords

cannabinoids
alkynes
alkenes
pharmacologically active compounds
CANNABINOID RECEPTOR
SELECTIVE ANTAGONIST
POTENT
BRAIN
PHARMACOLOGY
ANANDAMIDE
CHEMISTRY
ALCOHOLS
ANALOGS
BINDS

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10.1016/S0040-4020(99)00849-2

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title = "Development of agonists, partial agonists and antagonists in the Delta(8)-tetrahydrocannabinol series",

abstract = "Synthetic sequences were developed (Schemes 1 to 6) for the syntheses of various Delta(8)-THC analogs with either a rigid acetylenic linkage or a cis-double bond in different positions in the side chain. Various alkyne and cis-ene-Delta(8)-THC analogs were also synthesized carrying a functional group such as a cyano, isothiocyano, azido, amino, nitro, bromo, hydroxy, fluoro and a methoxy group at the chain terminal. The in vitro and in vivo pharmacology of these unique analogs have provided several ligands which are partial agonists or antagonists of the cannabinoid receptor CB1. The 2'-position in the side chain was found to be optimum for activity. (C) 1999 Elsevier Science Ltd. All rights reserved.",

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author = "Crocker, {P J} and B Saha and Ryan, {W J} and Wiley, {J L} and Martin, {B R} and Ross, {R A} and Pertwee, {R G} and Razdan, {R K}",

year = "1999",

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doi = "10.1016/S0040-4020(99)00849-2",

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T1 - Development of agonists, partial agonists and antagonists in the Delta(8)-tetrahydrocannabinol series

AU - Crocker, P J

AU - Saha, B

AU - Ryan, W J

AU - Wiley, J L

AU - Martin, B R

AU - Ross, R A

AU - Pertwee, R G

AU - Razdan, R K

PY - 1999/12/3

Y1 - 1999/12/3

N2 - Synthetic sequences were developed (Schemes 1 to 6) for the syntheses of various Delta(8)-THC analogs with either a rigid acetylenic linkage or a cis-double bond in different positions in the side chain. Various alkyne and cis-ene-Delta(8)-THC analogs were also synthesized carrying a functional group such as a cyano, isothiocyano, azido, amino, nitro, bromo, hydroxy, fluoro and a methoxy group at the chain terminal. The in vitro and in vivo pharmacology of these unique analogs have provided several ligands which are partial agonists or antagonists of the cannabinoid receptor CB1. The 2'-position in the side chain was found to be optimum for activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

AB - Synthetic sequences were developed (Schemes 1 to 6) for the syntheses of various Delta(8)-THC analogs with either a rigid acetylenic linkage or a cis-double bond in different positions in the side chain. Various alkyne and cis-ene-Delta(8)-THC analogs were also synthesized carrying a functional group such as a cyano, isothiocyano, azido, amino, nitro, bromo, hydroxy, fluoro and a methoxy group at the chain terminal. The in vitro and in vivo pharmacology of these unique analogs have provided several ligands which are partial agonists or antagonists of the cannabinoid receptor CB1. The 2'-position in the side chain was found to be optimum for activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

KW - cannabinoids

KW - alkynes

KW - alkenes

KW - pharmacologically active compounds

KW - CANNABINOID RECEPTOR

KW - SELECTIVE ANTAGONIST

KW - POTENT

KW - BRAIN

KW - PHARMACOLOGY

KW - ANANDAMIDE

KW - CHEMISTRY

KW - ALCOHOLS

KW - ANALOGS

KW - BINDS

U2 - 10.1016/S0040-4020(99)00849-2

DO - 10.1016/S0040-4020(99)00849-2

M3 - Article

SN - 0040-4020

VL - 55

SP - 13907

EP - 13926

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -

Development of agonists, partial agonists and antagonists in the Delta(8)-tetrahydrocannabinol series

Abstract

Keywords

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