Literature DB >> 15781390

The novel GABA adamantane derivative (AdGABA): design, synthesis, and activity relationship with gabapentin.

Grigoris Zoidis1, Ioannis Papanastasiou, Ioannis Dotsikas, Alejandro Sandoval, Raquel Gouvea Dos Santos, Zeta Papadopoulou-Daifoti, Alexander Vamvakides, Nicolas Kolocouris, Ricardo Felix.   

Abstract

A facile preparation of 2-aminomethyl-2-tricyclo[3.3.1.1(1,7)]decaneacetic acid hydrochloride 5 (AdGABA) is described. The synthesis of AdGABA involves the hydrogenation of 2-cyano-2-tricyclo[3.3.1.1(1,7)]decaneacetic acid 11, which was synthesized by two different synthetic routes. AdGABA was found to antagonize the pentylenetetrazole (PTZ) and semicarbazide (SCZ) induced tonic convulsions and exhibits analgesic activity in the hot plate test on mice. Although its mechanism of action is quite similar to that proposed previously for gabapentin (interaction with the alpha2delta subunit of the voltage gated Ca2+ channels), further studies were undertaken in order to clarify the precise mechanism of the anticonvulsant and analgesic effects of AdGABA on a molecular level.

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Year:  2005        PMID: 15781390     DOI: 10.1016/j.bmc.2005.02.030

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  7 in total

Review 1.  The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.

Authors:  Lukas Wanka; Khalid Iqbal; Peter R Schreiner
Journal:  Chem Rev       Date:  2013-02-25       Impact factor: 60.622

2.  Identification of a disulfide bridge essential for structure and function of the voltage-gated Ca(2+) channel α(2)δ-1 auxiliary subunit.

Authors:  Aida Calderón-Rivera; Arturo Andrade; Oscar Hernández-Hernández; Ricardo González-Ramírez; Alejandro Sandoval; Manuel Rivera; Juan Carlos Gomora; Ricardo Felix
Journal:  Cell Calcium       Date:  2011-11-03       Impact factor: 6.817

3.  Design, synthesis, and trypanocidal activity of new aminoadamantane derivatives.

Authors:  Ioannis Papanastasiou; Andrew Tsotinis; Nicolas Kolocouris; S Radhika Prathalingam; John M Kelly
Journal:  J Med Chem       Date:  2008-02-19       Impact factor: 7.446

4.  Regulation of high-voltage-activated Ca2+ channel function, trafficking, and membrane stability by auxiliary subunits.

Authors:  Ricardo Felix; Aida Calderón-Rivera; Arturo Andrade
Journal:  Wiley Interdiscip Rev Membr Transp Signal       Date:  2013-09-01

5.  The alpha(2)delta subunit augments functional expression and modifies the pharmacology of Ca(V)1.3 L-type channels.

Authors:  Arturo Andrade; Alejandro Sandoval; Ricardo González-Ramírez; Diane Lipscombe; Kevin P Campbell; Ricardo Felix
Journal:  Cell Calcium       Date:  2009-09-30       Impact factor: 6.817

6.  Anti-Seizure Activity of 1-Adamantane Carboxylic Acid in Common Experimental Seizure Models: Role of Benzodiazepine-GABAA Receptors.

Authors:  Elham Ghanbari; Hakimeh Gavzan; Bahar Khoshkroodian; Mohammad Sayyah
Journal:  Iran Biomed J       Date:  2021-05-01

Review 7.  Opioid-induced hyperalgesia in chronic pain patients and the mitigating effects of gabapentin.

Authors:  Nicoleta Stoicea; Daric Russell; Greg Weidner; Michael Durda; Nicholas C Joseph; Jeffrey Yu; Sergio D Bergese
Journal:  Front Pharmacol       Date:  2015-05-27       Impact factor: 5.810

  7 in total

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