Synthesis and Characterization of 2-substituted Bornane Pharmacophores for Novel Cannabinergic Ligands

Overview

Journal Tetrahedron Lett

Publisher Elsevier

Specialty Chemistry

Date 2013 Aug 13

PMID 23935221

Citations 7

Authors

Richard I Duclos Jr

Dai Lu

Jianxin Guo

Alexandros Makriyannis

Affiliations

Soon will be listed here.

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.

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References

Cincinelli R, Dallavalle S, Nannei R, Merlini L, Penco S, Giannini G . Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids. Bioorg Med Chem. 2007; 15(14):4863-75. DOI: 10.1016/j.bmc.2007.04.057. View

Lu D, Guo J, Duclos Jr R, Bowman A, Makriyannis A . Bornyl- and isobornyl-Delta8-tetrahydrocannabinols: a novel class of cannabinergic ligands. J Med Chem. 2008; 51(20):6393-9. PMC: 3700413. DOI: 10.1021/jm8005299. View

Webster S, Ward P, Binnie M, Craigie E, McConnell K, Sooy K . Discovery and biological evaluation of adamantyl amide 11beta-HSD1 inhibitors. Bioorg Med Chem Lett. 2007; 17(10):2838-43. DOI: 10.1016/j.bmcl.2007.02.057. View

Lu D, Meng Z, Thakur G, Fan P, Steed J, Tartal C . Adamantyl cannabinoids: a novel class of cannabinergic ligands. J Med Chem. 2005; 48(14):4576-85. DOI: 10.1021/jm058175c. View

Steinbrecher T, Hrenn A, Dormann K, Merfort I, Labahn A . Bornyl (3,4,5-trihydroxy)-cinnamate--an optimized human neutrophil elastase inhibitor designed by free energy calculations. Bioorg Med Chem. 2007; 16(5):2385-90. DOI: 10.1016/j.bmc.2007.11.070. View

Jarbe T, DiPatrizio N, Lu D, Makriyannis A . (-)-Adamantyl-delta8-tetrahydrocannabinol (AM-411), a selective cannabinoid CB1 receptor agonist: effects on open-field behaviors and antagonism by SR-141716 in rats. Behav Pharmacol. 2004; 15(7):517-21. DOI: 10.1097/00008877-200411000-00008. View

Yuasa Y, Nagakura A, Tsuruta H . Synthesis and sweetness characteristics of L-aspartyl-D-alanine fenchyl esters. J Agric Food Chem. 2001; 49(10):5013-8. DOI: 10.1021/jf010344o. View

Brown A, Bunnage M, Glossop P, James K, Jones R, Lane C . The discovery of adamantyl-derived, inhaled, long acting beta(2)-adrenoreceptor agonists. Bioorg Med Chem Lett. 2008; 18(4):1280-3. DOI: 10.1016/j.bmcl.2008.01.034. View

Yu Z, Sawkar A, Whalen L, Wong C, Kelly J . Isofagomine- and 2,5-anhydro-2,5-imino-D-glucitol-based glucocerebrosidase pharmacological chaperones for Gaucher disease intervention. J Med Chem. 2007; 50(1):94-100. PMC: 2543937. DOI: 10.1021/jm060677i. View

10.

Pearson A, Gontcharov A . Asymmetric Conversion of Arenechromium Complexes to Functionalized Cyclohexenones: Progress toward Defining an Optimum Chiral Auxiliary. J Org Chem. 2001; 63(1):152-162. DOI: 10.1021/jo971676o. View

11.

Luk T, Jin W, Zvonok A, Lu D, Lin X, Chavkin C . Identification of a potent and highly efficacious, yet slowly desensitizing CB1 cannabinoid receptor agonist. Br J Pharmacol. 2004; 142(3):495-500. PMC: 1574962. DOI: 10.1038/sj.bjp.0705792. View

12.

Janusz J, Gardlik J, Young P, Burkes R, Stoll S, Estelle A . High potency dipeptide sweeteners. 1. L-aspartyl-D-phenylglycine esters. J Med Chem. 1990; 33(3):1052-61. DOI: 10.1021/jm00165a027. View

13.

McLaughlin P, Lu D, Winston K, Thakur G, Swezey L, Makriyannis A . Behavioral effects of the novel cannabinoid full agonist AM 411. Pharmacol Biochem Behav. 2005; 81(1):78-88. DOI: 10.1016/j.pbb.2005.02.005. View

14.

Rohde J, Pliushchev M, Sorensen B, Wodka D, Shuai Q, Wang J . Discovery and metabolic stabilization of potent and selective 2-amino-N-(adamant-2-yl) acetamide 11beta-hydroxysteroid dehydrogenase type 1 inhibitors. J Med Chem. 2007; 50(1):149-64. DOI: 10.1021/jm0609364. View

15.

McLaughlin P, Brown C, Winston K, Thakur G, Lu D, Makriyannis A . The novel cannabinoid agonist AM 411 produces a biphasic effect on accuracy in a visual target detection task in rats. Behav Pharmacol. 2005; 16(5-6):477-86. DOI: 10.1097/00008877-200509000-00022. View

16.

Barth F, Millan J, Derocq J, Casellas P, Congy C, Oustric D . SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor. J Pharmacol Exp Ther. 1998; 284(2):644-50. View