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Literature DB >> 23935221

Synthesis and characterization of 2-substituted bornane pharmacophores for novel cannabinergic ligands.

Richard I Duclos¹, Dai Lu, Jianxin Guo, Alexandros Makriyannis.

Abstract

Analogously to the fenchyl and adamantyl groups, the bornyl and epimeric isobornyl groups are compact lipophilic substituents that can be incorporated into drug design to improve pharmacological or physicochemical properties. Methods are reported for the synthesis and characterization of 2-substituted norbornanes and bornanes that can serve as novel cannabinergic ligand intermediates.

Entities: Chemical Gene

Keywords: Bornyl; Chiral HPLC; Isobornyl; NMR; Norbornane

Year: 2008 PMID： 23935221 PMCID： PMC3738215 DOI： 10.1016/j.tetlet.2008.07.029

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

15 in total

1. Behavioral effects of the novel cannabinoid full agonist AM 411.

Authors: Peter J McLaughlin; Dai Lu; Keisha M Winston; Ganesh Thakur; Lynn A Swezey; Alexandros Makriyannis; John D Salamone
Journal: Pharmacol Biochem Behav Date: 2005-04-21 Impact factor: 3.533

2. Discovery and biological evaluation of adamantyl amide 11beta-HSD1 inhibitors.

Authors: Scott P Webster; Peter Ward; Margaret Binnie; Eilidh Craigie; Kirsty M M McConnell; Karen Sooy; Andy Vinter; Jonathan R Seckl; Brian R Walker
Journal: Bioorg Med Chem Lett Date: 2007-02-25 Impact factor: 2.823

3. Discovery and metabolic stabilization of potent and selective 2-amino-N-(adamant-2-yl) acetamide 11beta-hydroxysteroid dehydrogenase type 1 inhibitors.

Authors: Jeffrey J Rohde; Marina A Pliushchev; Bryan K Sorensen; Dariusz Wodka; Qi Shuai; Jiahong Wang; Steven Fung; Katina M Monzon; William J Chiou; Liping Pan; Xiaoqing Deng; Linda E Chovan; Atul Ramaiya; Mark Mullally; Rodger F Henry; DeAnne F Stolarik; Hovis M Imade; Kennan C Marsh; David W A Beno; Thomas A Fey; Brian A Droz; Michael E Brune; Heidi S Camp; Hing L Sham; Ernst Uli Frevert; Peer B Jacobson; J T Link
Journal: J Med Chem Date: 2007-01-11 Impact factor: 7.446

4. Isofagomine- and 2,5-anhydro-2,5-imino-D-glucitol-based glucocerebrosidase pharmacological chaperones for Gaucher disease intervention.

Authors: Zhanqian Yu; Anu R Sawkar; Lisa J Whalen; Chi-Huey Wong; Jeffery W Kelly
Journal: J Med Chem Date: 2007-01-11 Impact factor: 7.446

5. The discovery of adamantyl-derived, inhaled, long acting beta(2)-adrenoreceptor agonists.

Authors: Alan D Brown; Mark E Bunnage; Paul A Glossop; Kim James; Rhys Jones; Charlotte A L Lane; Russell A Lewthwaite; Simon Mantell; Christelle Perros-Huguet; David A Price; Mike Trevethick; Rob Webster
Journal: Bioorg Med Chem Lett Date: 2008-01-12 Impact factor: 2.823

6. SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor.

Authors: M Rinaldi-Carmona; F Barth; J Millan; J M Derocq; P Casellas; C Congy; D Oustric; M Sarran; M Bouaboula; B Calandra; M Portier; D Shire; J C Brelière; G L Le Fur
Journal: J Pharmacol Exp Ther Date: 1998-02 Impact factor: 4.030

7. The novel cannabinoid agonist AM 411 produces a biphasic effect on accuracy in a visual target detection task in rats.

Authors: P J McLaughlin; C M Brown; K M Winston; G Thakur; D Lu; A Makriyannis; J D Salamone
Journal: Behav Pharmacol Date: 2005-09 Impact factor: 2.293

8. Asymmetric Conversion of Arenechromium Complexes to Functionalized Cyclohexenones: Progress toward Defining an Optimum Chiral Auxiliary.

Authors: Anthony J. Pearson; Alexander V. Gontcharov
Journal: J Org Chem Date: 1998-01-09 Impact factor: 4.354

9. (-)-Adamantyl-delta8-tetrahydrocannabinol (AM-411), a selective cannabinoid CB1 receptor agonist: effects on open-field behaviors and antagonism by SR-141716 in rats.

Authors: T U C Järbe; N V DiPatrizio; D Lu; A Makriyannis
Journal: Behav Pharmacol Date: 2004-11 Impact factor: 2.293

10. Bornyl (3,4,5-trihydroxy)-cinnamate--an optimized human neutrophil elastase inhibitor designed by free energy calculations.

Authors: Thomas Steinbrecher; Andrea Hrenn; Korinna L Dormann; Irmgard Merfort; Andreas Labahn
Journal: Bioorg Med Chem Date: 2007-11-29 Impact factor: 3.641

7 in total

1. Synthesis and characterization of a compact tricyclic resorcinol from (+)- and (-)-3-pinanol.

Authors: Dai Lu; Spyros P Nikas; Xiu-Wen Han; Damon A Parrish; Alexandros Makriyannis
Journal: Tetrahedron Lett Date: 2012-08-29 Impact factor: 2.415

2. Bornyl- and isobornyl-Delta8-tetrahydrocannabinols: a novel class of cannabinergic ligands.

Authors: Dai Lu; Jianxin Guo; Richard I Duclos; Anna L Bowman; Alexandros Makriyannis
Journal: J Med Chem Date: 2008-10-01 Impact factor: 7.446

Review 3. Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors: Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal: Chem Rev Date: 2020-01-06 Impact factor: 60.622