☆ 4.2 Article

Preparation and testing of homocubyl amines as therapeutic NMDA receptor antagonists

MEDICINAL CHEMISTRY RESEARCH (2013)

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期刊

MEDICINAL CHEMISTRY RESEARCH
卷 22, 期 1, 页码 360-366

出版社

SPRINGER BIRKHAUSER
DOI: 10.1007/s00044-012-0029-7

关键词

Bishomocubyl-10-amine; Cubylamine; Homocubyl-9-amine; Memantine; NMDA antagonist; Trishomocubyl-4-amine

类别

Chemistry, Medicinal

资金

  1. Ministry of Science and Education of Ukraine
  2. Merz Pharma GmbH Co.

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Computational modeling demonstrates that the van-der-Waals surfaces of homocubyl amines are similar to that of the neuroprotector Memantine (R). Utilizing readily available precursors we report the preparation of a series of homological cubylamines, namely pentacyclo[6.3.0.0(2,6).0(3,10).0(5,9)]undecyl-4-amine (trishomocubyl-4-amine, 2), pentacyclo[5.3.0.0(2,5). 0(3,9).0(4,8)]decyl-10-amine (bishomocubyl-10-amine, 3), pentacyclo[4.3.0.0(2,5).0(3,8).0(4,7)]nonyl-9-amine (homocubyl-9-amine, 4), and pentacyclo[4.2.0.0(2,5).0(3,8).0(4,7)]octyl-1-amine (cubylamine, 5). The hydrochlorides of amines 2-5 show pronounced affinity for the (+) MK-801 channel binding site, and it seems likely that these compounds would act as very fast voltage-dependent NMDA receptor antagonists.

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