Zoidis Grigoris, Papanastasiou Ioannis, Dotsikas Ioannis, Sandoval Alejandro, Dos Santos Raquel Gouvea, Papadopoulou-Daifoti Zeta, Vamvakides Alexander, Kolocouris Nicolas, Felix Ricardo
Faculty of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Panepistimioupoli-Zografou, GR-15771 Athens, Greece.
Bioorg Med Chem. 2005 Apr 15;13(8):2791-8. doi: 10.1016/j.bmc.2005.02.030.
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.
本文描述了一种简便的制备2-氨甲基-2-三环[3.3.1.1(1,7)]癸烷乙酸盐酸盐5（AdGABA）的方法。AdGABA的合成涉及2-氰基-2-三环[3.3.1.1(1,7)]癸烷乙酸11的氢化反应，而11是通过两种不同的合成路线合成的。研究发现，AdGABA可拮抗戊四氮（PTZ）和氨基脲（SCZ）诱导的强直性惊厥，并在小鼠热板试验中表现出镇痛活性。尽管其作用机制与先前提出的加巴喷丁的作用机制相当相似（与电压门控Ca2+通道的α2δ亚基相互作用），但为了在分子水平上阐明AdGABA抗惊厥和镇痛作用的精确机制，仍进行了进一步的研究。
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