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Note | Regular issue | Vol 78, No. 10, 2009, pp.2549-2558
Published online, 5th June, 2009
DOI: 10.3987/COM-09-11722
Synthesis of Two Novel Water-soluble Cleft-Type Cyclophanes Effective as N-Methyl-D-aspartate Receptor Antagonist

Takashi Masuko, Yuta Nemoto, Tadashi Kusama, Koichi Metori, Yasuo Kizawa, and Muneharu Miyake*

*College of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi-shi, Chiba 274-8555, Japan


Novel cleft-type cyclophanes, 4,4′-bis[N-(5-dimethylaminonaphthalene-sulfonylaminoethyl)-N-(1,4,7,10-tetraazacyclododecane-1-ylacetyl)-2-aminoethoxy]diphenylmethane octahydrochloride (1a, DNCn) and 4,4′-bis[N-(p-toluene-sulfonylaminoethyl)-N-(1,4,7,10-tetraazacyclododecane-1-ylacetyl-2-aminoethoxy]diphenylmethane octahydrochloride (1b, TsDCn) having an effective role as N-methyl-D-aspartate (NMDA) receptor antagonist were synthesized. Neuroprotective effects of cleft-type cyclophanes, DNCn (1a) and TsDCn (1b) against cell damage caused by NMDA were measured in cultured rat hippocampal neurons. DNCn (1a) and TsDCn (1b) reduced the neurotoxicity and acted as open channel blocker for NMDA receptor.