Conformationally Restricted GABA Analogs: From Rigid Carbocycles to Cage Hydrocarbons

• Roberts E , FrankelS. γ-Aminobutyric acid in brain: its formation from glutamic acid.J. Biol. Chem.187, 55–63 (1950).
   PubMed Web of Science ®Google Scholar
• Boistel J , FattP. Membrane permeability change during inhibitory transmitter action in crustacean muscle.J. Physiol. (Lond.)144, 176–191 (1958).
   Google Scholar
• Coombs JS , EcclesJC, FattP. The specific ionic conductances and the ionic movements across the motoneuronal membrane that produce the inhibitory postsynaptic potential.J. Physiol. (Lond.)130, 326–373 (1955).
   Google Scholar
• Krnjevic K , SchwartzS. The action of γ-aminobutyric acid on cortical neurones.Exp. Brain Res.3, 320–336 (1967).
   PubMed Web of Science ®Google Scholar
• Nicholson SH , SucklingCJ, IversenLL. GABA analogues: conformational analysis of effects on [3H]GABA binding to postsynaptic receptors in human cerebellum.J. Neurochem.32, 249–252 (1979).
   PubMed Web of Science ®Google Scholar
• Johnston GAR , CurtisDR, BeartPM, GameCJA, MccullochRM, TwitchinB. Cis- and trans-4-aminocrotonic acid as GABA analogues of restricted conformation. J. Neurochem.24, 157–160 (1975).
   PubMed Web of Science ®Google Scholar
• Segal M , SimsK, AndsmissmanE. Characterisation of an inhibitory receptor in rat hippocampus: a microiontophoretic study using conformationally restricted amino acid analogues.Br. J. Pharmacol.54, 181–188 (1975).
   PubMed Web of Science ®Google Scholar
• Johnston GAR , AllanRD, KennedySME, TwitchinB. A systematic study of GABA analogues of restricted conformation. In: GABA-Neurotransmitters. Kofod H, Krogsgaard-Larsen P, Scheel-Kruger J (Eds). Munksgaard, Copenhagen, Denmark 149–164 (1978).
   Google Scholar
• Krogsgaard-Larsen P , JohnstonGAR, LodgeD, CurtisDR. A new class of GABA agonist.Nature268, 53–55 (1977).
   PubMed Web of Science ®Google Scholar
• Krogsgaard-Larsen P , JohnstonGAR, CurtisDR, GameCJA, MccullochRM. Structure and biological activity of a series of conformationalty restricted analogues of GABA.J. Neurochem.25, 803–809 (1975).
   PubMed Web of Science ®Google Scholar
• Allan RD , CurtisDR, HeadleyP, JohnsonDR, LodgeD, TwitchinB. The synthesis and activity of cis-and trans-2-(aminomethyl) cyclopropanecarboxylic acid as conformationally restricted analogues of GABA. J. Neurochem.34(3), 652–654 (1980).
   PubMed Web of Science ®Google Scholar
• Paulini K , Reissig H-U. Ein effektiver Weg zu GABA-analogen Aminosauren: Cyclopropanierung von N-silylierten Allylaminen und Enaminen. Liebigs Ann. Chem.455–461 (1991).
   Google Scholar
• Galeazzi R , MobbiliG, OrenaM. From 3-aza-2-oxobicyclo[3.1.0]hexane to enantiopure disubstituted cyclopropane: a convenient approach to cis-2,3-methano-GABA. Tetrahedron. Asymm.8(1), 133–137 (1997).
   Google Scholar
• Galeazzi R , MobbiliG, OrenaM. A convenient approach to diastereomerically pure 1,3,4-trisubstituted pyrrolidin-2-ones by intramolecular cyclisation of N-(2-alken-1-yl)amides mediated by Mn(III). An entry to both (R)- and (S)-3-pyrrolidineacetic acid. Tetrahedron52, 1069–1084 (1996).
   Web of Science ®Google Scholar
• Rodríguez-Soria V , QuinteroL, Sartillo-PiscilF. A novel stereoselective tin-free radical protocol for the enantioselective synthesis of pyrrolidinones and its application to the synthesis of biologically active GABA-derivatives.Tetrahedron64, 2750–2754 (2008).
   Web of Science ®Google Scholar
• Duke RK , AllanRD, ChebibM, GreenwoodJR, JohnsonDR. Resolution and conformational analysis of diastereoisomeric esters of cis- and trans-2-(aminomethyl)-1-carboxycyclopropanes. Tetrahedron Assym.9, 2533–2548 (1998).
   Google Scholar
• Duke RK , ChebibM, BalcarVJ, AllanRD, MewettKN, JohnsonGAR. (+)- and (–)-cis-2-aminomethylcyclopropanecarboxylic acids show opposite pharmacology at recombinant ρ1 and ρ2 GABAC receptors. J. Neurochem.75(6), 2602–2610 (2000).
   PubMed Web of Science ®Google Scholar
• Allan RD , CurtisR, HeadleyPMet al. Cyclobutane analogs of GABA. Neurochem. Res. 5(4), 393–400 (1980).
   PubMed Web of Science ®Google Scholar
• Baxendale IR , ErnstM, Krahnert W-R, Ley SV. Application of polymer-supported enzymes and reagents in the synthesis of γ-aminobutyric acid (GABA) analogues. Synlett10, 1641–1644 (2002).
   Google Scholar
• Chenevert R , MartinR. Enantioselective synthesis of (+) and (–)-cis-3-aminocyclo-pentanecarboxylic acids by enzymatic asymmetrization. Tetrahedron Asymm.3, 199–200 (1992).
   Google Scholar
• Allan RD , JohnsonDR, TwitchinB. Synthesis of analogues of GABA. III. All four stereo-isomers of 3-aminocyclo-pentanecarboxylicacid and a stereochemical correlation with amidinomycin.Aust. J. Chem.32, 2517–2521 (1979).
   Web of Science ®Google Scholar
• Gee NS , BrownJP, DissanayakeVUK, OffordJ, ThurlowR, WoodruffGN. The novel anticonvulsant drug, gabapentin (Neurontin), binds to the α2δ subunit of a calcium channel. J. Biol. Chem.271, 5768–5776 (1996).
   PubMed Web of Science ®Google Scholar
• Stahl S . Anticonvulsants and the relief of chronic pain: pregabalin and gabapentin as α2δ ligands at voltage-gated calcium channels. J. Clin. Psychiatry65, 596–597 (2004).
   PubMed Web of Science ®Google Scholar
• Taylor CP , GeeNS, Su T-Z et al. A summary of mechanistic hypotheses of gabapentin pharmacology. Epilepsy Res.29, 233–249 (1998).
   PubMed Web of Science ®Google Scholar
• McLean M . Gabapentin in the management of convulsive disorders.Epilepsia40 (Suppl. 6), S39–S50 (1999).
   PubMedGoogle Scholar
• Rowbotham M , HardenN, StaceyB, BernsteinP, Magnus-MillerL. Gabapentin for the treatment of postherpetic neuralgia: a randomized controlled trial.J. Am. Med. Assoc.280, 1837–1842 (1998).
   PubMed Web of Science ®Google Scholar
• Rice A , MatonS. Gabapentin in postherpetic neuralgia: a randomised, double blind, placebo controlled study.Pain94, 215–224 (2001).
   PubMed Web of Science ®Google Scholar
• Garcia-Borreguero D , LarrosaO, de la Llave Y, Verger K, Masramon X, Hernandez G. Treatment of restless legs syndrome with gabapentin: a double-blind, cross-over study. Neurology59, 1573–1579 (2002).
   PubMed Web of Science ®Google Scholar
• Pollack M , MatthewsJ, ScottE. Gabapentin as a potential treatment for anxiety disorders.Am. J. Psychiatry155, 992–993 (1998).
   PubMed Web of Science ®Google Scholar
• Backonja M , BeydounA, EdwardsKet al. Gabapentin for the symptomatic treatment of painful neuropathy in patients with diabetes mellitus: a randomized controlled trial. J. Am. Med. Assoc. 280, 1831–1836 (1998).
   PubMed Web of Science ®Google Scholar
• McLean M . Gabapentin.Epilepsia36 (Suppl. 2), S73–S86 (1995).
   PubMedGoogle Scholar
• Gidal B , RadulovicL, KrugerS, RuteckiP, PitterleM, BockbraderH. Inter- and intra-subject variability in gabapentin absorption and absolute bioavailability.Epilepsy Res.40, 123–127 (2000).
   PubMed Web of Science ®Google Scholar
• Boyd R , TurckD, AbelR, SedmanA, BockbraderH. Effects of age and gender on single-dose pharmacokinetics of gabapentin.Epilepsia40, 474–479 (1999).
   PubMed Web of Science ®Google Scholar
• Gidal B , DeCerceJ, BockbraderHet al. Gabapentin bioavailability: effect of dose and frequency of administration in adult patients with epilepsy. Epilepsy Res. 31(2), 91–99 (1998).
   PubMed Web of Science ®Google Scholar
• Bryans JS , WustrowDJ. 3-substituted GABA analogs with central nervous system activity: a review.Med. Res. Rev.19(2), 149–177 (1999).
   PubMed Web of Science ®Google Scholar
• Griffiths G , MettlerH, MillsL, PrevidoliF. Novel syntheses of gabapentin via addition of hydrocyanic acid to cyclohexylidenemalonate or cyano(cyclohexylidene)acetate.Helv. Chim. Acta74, 309–314 (1991).
   Web of Science ®Google Scholar
• Bryans JS , HorwellDC, RatcliffeGS, Receveur J-M, Rubin JR. An in vitro investigation into conformational aspects of gabapentin. Bioorg. Med. Chem.7, 715–721 (1999).
   PubMed Web of Science ®Google Scholar
• Bryans JS , DaviesN, GeeNSet al. Identification of novel ligands for the gabapentin binding site on the α2δ subunit of a calcium channel and their evaluation as anticonvulsant agents. J. Med. Chem. 41(11), 1838–1845 (1998).
   PubMed Web of Science ®Google Scholar
• Rogawski MA , WenkGL. The neuropharmacological basis for the use of memantine in the treatment of Alzheimer’s disease.CNS Drug Rev.9(3), 275–308 (2003).
   PubMedGoogle Scholar
• Germane SK , PolisYY, KarinyaLY. Action of midantane, remantadine, and its alkyl analogs on the central nervous system.Pharmaceut. Chem. J.11(6), 798-802 (1977).
   Google Scholar
• Berzinya DA , KimenisAA. Influence of adapromin on the content of catecholamines in the body of white rats.Exp. Clin. Farmacoterapia15, 50–53 (1986).
   Google Scholar
• Krapivin SV , SergeevaSA. Comparative analysis of the effects of adapromine, midantane, and bromantane on bioelectrical activity of rat brain.Bull. Exp. Biol. Med.125(2), 151–155 (1998).
   Web of Science ®Google Scholar
• Kamianov I , AndreziniaRA. The antiparkinson activity of gludantan (preliminary report).Zh Nevropatol Psikhiatr Im. S.S.Korsakova75(6), 910–916 (1975).
   PubMedGoogle Scholar
• Liubimov BI , SkoldinovAP, BoikoSS. Pharmacokinetic study of 2-(N-benzylamino)adamatane (bemantan) by a gas-liquid chromatographic method. Farmakol. Toksikol.43(4), 408–411 (1980).
   PubMedGoogle Scholar
• Boiko SS , ZherdevVP, KisliakNA. Interspecific differences in kemantan pharmacokinetics.Farmakol. Toksikol.1991(54), 1 (1991).
   Google Scholar
• Molecular Building Blocks for Nanotechnology . MansooriGA, GeorgeTF, AssoufidL, ZhangG (Eds). Springer, NY, USA (2007).
   Google Scholar
• Eaton PE . Synthesis of specific polynitrocubanes. In: Scholarly Research in Explosive Research & Characterization. Geo-Centers Inc., MA, USA, 22 (1993).
   Google Scholar
• Taylor BN . Unusual solid state properties of cubane discovered.J. Res. NIST102(5), 600 (1997).
   Google Scholar
• Bashir-Hashemi A . Cubanes: super explosives and potential pharmaceutical intermediates.NASA, Washington, Technology 2003; The Fourth National Technology Transfer Conference and Exposition1, 127–130 (2003).
   Google Scholar
• Bashir-Hashemi A . Chemistry and structure of phenylcubanes.J. Org. Chem.55(2), 416–420 (1990).
   Web of Science ®Google Scholar
• Levandovsky IA , SharapaDI, CherenkovaOA, GaidaiAV, ShubinaTE. The chemistry of D3-trishomocubane. Russ. Chem. Rev.79(11), 1089 (2010).
   Google Scholar
• Geldenhuys WJ , MalanSF, MarchandAP. Pharmacology and structure–activity relationships of bioactive polycyclic cage compounds: a focus on pentacycloundecane derivatives.Med. Res. Rev.25(1), 21–48 (2005).
   PubMed Web of Science ®Google Scholar
• Liu X , NuwayhidS, ChristieMJ, KassiouM, WerlingLL. Trishomocubanes: novel σ ligands modulate amphetamine-stimulated [3H]dopamine release.Eur. J. Pharmacol.422, 39–45 (2001).
   PubMed Web of Science ®Google Scholar
• Wilcox C Jr, Leung C. Preparation of 4-substituted-bicyclo[2.2.1]heptane-1-carboxylic acids. J. Org. Chem.33(2), 877–880 (1968).
   Web of Science ®Google Scholar
• Davies WL , GrunertRR, HaffRFet al. Antiviral activity of 1-adamantanamine (amantadine). Science 144, 862–863 (1964).
   PubMed Web of Science ®Google Scholar
• Stanicova J , MiskovskyP, SutiakV. Amantadine: anantiviral and antiparkinsonian agent.Vet. Med. Czech46, 224–256 (2001).
   Web of Science ®Google Scholar
• Younossi ZM , PerrilloRP. The roles of amantadine, rimantadine, ursodeoxycholic acid, and NSAIDs, alone or in combination with alpha interferons, in the treatment of chronic hepatitis C.Semin. Liver Dis.19(Suppl. 1), 662–668 (1999).
   Google Scholar
• Smith JP , RileyTR, DevenyiA, BingamanSI, KunselmanA. Amantadine therapy for chronic hepatitis C.J. Gen. Intern. Med.19, 662–668 (2004).
   PubMed Web of Science ®Google Scholar
• Galbraith AW . Prevention of post-herpetic neuralgia by amantadine hydrochloride (Symmetrel).Br. J. Clin. Pract.37, 304–306 (1983).
   PubMedGoogle Scholar
• Thompson M , BonesM. Nontraditional analgesics for the management of postherpetic neuralgia.Clin. Pharm.4, 170–176 (1985).
   PubMedGoogle Scholar
• Van der Schyf CJ , GeldenhuysWJ. Polycyclic compounds: ideal drug scaffolds for the design of multiple mechanism drugs?Neurotherapeutics6(1), 175 (2009).
   PubMed Web of Science ®Google Scholar
• Black RM . Synthesis of the four stereoisomers of 4-aminoadamantane-2-carboxylic acid, rigid analogues of γ-aminobutyric acid.J. Chem. Soc. Perkin Trans.1, 73–77 (1982).
   Google Scholar
• Stepanov FN , Srebrodol‘skiiYI. Acid hydrolysis of acylamido derivatives of adamantane.Vestnik Kievskogo Politekhnicheskogo Instituta2, 6–10 (1966).
   Google Scholar
• Wanka L , CabreleC, VanejewsM, SchreinerPR. γ-aminoadamantanecarboxylic acids through direct C–H bond amidations.Eur. J. Org. Chem.2007(9), 1474–1490 (2007).
   Web of Science ®Google Scholar
• Olah GA , GuptaGB, NarangSC. Synthetic methods and reactions; 661. nitrosonium ion induced preparation of amides from alkyl (arylalkyl) halides with nitriles, a mild and selective ritter-type reaction.Synthesis274–276 (1979).
   Google Scholar
• Schreiner PR , LauensteinO, KolomitsinIV, NadiS, FokinAA. Selective C–H activation of aliphatic hydrocarbons under phase-transfer conditions.Angew. Chem. Int. Ed.37, 1895–1897 (1998).
   Web of Science ®Google Scholar
• Schreiner PR , LauensteinO, ButovaEDet al. Selective radical reactions in multiphase systems: phase-transfer halogenations of alkanes. Chem. Eur. J. 7, 4996–5003 (2001).
   PubMed Web of Science ®Google Scholar
• Zoidis G , PapanastasiouI, DotsikasIet al. The novel GABA adamantane derivative (AdGABA): design, synthesis, and activity relationship with gabapentin. Bioorg. Med. Chem. 13, 2791–2798 (2005).
   PubMed Web of Science ®Google Scholar
• Lanneau C , GreenA, HirstWDet al. Gabapentin is not a GABAB receptor agonist. Neuropharmacology 41(8), 965–975 (2001).
   PubMed Web of Science ®Google Scholar

Patents

• Hartenstein J, Satzinger G, Herrmann M. German Patent 2626467 (1977).
   Google Scholar
• Satzinger G, Hartenstein J, Herrmann M. German Patent 2543821 (1977).
   Google Scholar
• Jennings R, Johnson D, Seamans R, Zeller J. US5319135 (1994).
   Google Scholar
• Ferrari M, Ghezzi M, Belotti P. US6846950 (2005).
   Google Scholar
• Geigy JR. NL6600715 (1966).
   Google Scholar