ChemInform Abstract: Pentacyclo(5.4.0.02,6.03,10.05,9)undecylamines. Synthesis and Pharmacology.

Abstract

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New oxapolycyclic cage amines with NMDA receptor antagonist and trypanocidal activities

“…8 Biological activity has also been found with other polycyclic cage amines. 9 For example, 1 displayed in vivo activity against herpex simplex-II and influenza A2 virus, 10 2 was studied as an anti-Parkinsonian agent, 11 and cubylamine, 3, was found to be a MAO-B inhibitor ( Fig. 1).…”

Selective reductive dimerization of homocubane series oximes

“…Since the moment of the discovery of the activity of NGP1-01 (8-benzylamino-8,11-oxapentacyc lo [5.4.0.0 2,6 .0 3,10 .0 5,9 ]-undecane) as calcium antagonist [7] the biological activity of the aminopentacycloundecanes started to be more thoroughly investigated. The high efficiency was proved of NGP1-01 and a series of substituted pentacycloundecylamines as antagonists of the receptor of N-methyl-D-aspartate (NMDA) [8], and also the possibility was found to use NGP1-01 as a neuroprotector at the focal ischemia [9].…”

“…Especial interest is attracted by the derivatives of the most accessible pentacyclo- [5.4.0.0 2,6 .0 3,10 .0 5,9 ] undecane (С S -trishomocubane) and С 11 Н 14 -stable isomer of pentacyclo[6.3.0.0 2,6 .0 3,10 .0 5,9 ]undecane (D 3 -trishomocubane). The anticataleptic [4] and antiviral [5] activity of D 3 -trishomocubyl-4-amines was lately investigated. The anticataleptic activity was also found in С S -trishomocubyl-8-amines but their use is prevented by the high toxicity [6].…”

“…In the mixture of compounds II-IV only monoethylene ketals underwent the reaction giving the corresponding isomeric carboxy derivatives V and VI, whereas the bisethylene ketal remained intact and therefore was easily fi ltered off from the reaction mixture. Acids V and VI were precipitated from the mother liquor by adding concentrated hydrochloric acid under the pH control (4)(5). The yield of compounds V and VI depends on the degree of powdering the ketal mixture before the reaction and on the amount of water used in the treatment of the reaction mixture apparently because of the considerable solubility in water of carboxy derivatives V and VI.…”

“…We selected as the initial compound for the synthesis of di-6-pentacyclo[5.3.0.0 2,5 .0 3,9 .0 4,8 ]decylamine (XII) 1,9-dibromopentacyclo[5.4.0.0 2,6 .0 3,10 .0 5,9 ]undeca-8,11-dione (І) prepared along the described four-stage procedure [13] from hydroquinone and cyclopentadiene.…”