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Design and Synthesis of Azacyclophanes

Research Project

Project/Area Number 11672119
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionScience University of Tokyo

Principal Investigator

HARA Hiroshi  Sci.Univ.of Tokyo, Fac.of Pharm.Sci., Associate Professor, 薬学部, 助教授 (50096715)

Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2000: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1999: ¥500,000 (Direct Cost: ¥500,000)
Keywordsazacyclophane / cyclization / orthocyclophane / pharamacological activity / Writhing / Irwin's method / アザシクロファン / 閉環反応 / オルトシクロファン / 薬理作用 / ライジング反応 / Irwin法
Research Abstract

Azacyclophanes are host compounds suitable for complexation of guest in aqueous solution. Various type of azacyclophanes were investigated, however, 5-azacyclobenzylene derivatives have not been synthesized. We have already prepared 5-silacyclobenzylene compounds, which have a unique C_2 symmetrical structure. Therefore, a quatemary ammmonium salt (N,N-dialkyl-5-azacyclobenzylene) is promissing to be used as a chiral phase transfer catalyst. On the other hands, studies on biological activities of azacyclophanes have not been reported so far. We tried to construct the 5-azacyclobenzylene skeleton by two pathways. At first bis(6-bromoveratryl)veratrole, a useful synthestic block, was apllied to react with benzyl amine in the presence of palladium catalyst to construct the target skeleton, however, it failed to obtain 5-azacyclobenzylene derivatives. Second tactics involved employment bis(2-hydroxy-methylphenyl)amine as a starting material. 4-Chlro-2-(2-hydroxymethylphenyl)aminobenzyl alcohol, readily prepared from Lobenzarid【○!R】, was treated with veratrole under acidic conditions to give successfully 5-azacyclobenzylene derivative (1). The reaction with excess veratrole afforded an acyclic bis(veratrylphenyl)amine, cyclization of which into cyclotetrabenzylene with formalin under acidic conditions was tried to form bicyclic cyclophane unexpectedly. The structure of the product was not disclosed yet. The bis(veratryl-phenyl)amine was methylated with formalin and NaBH_4 to give the corresponding N-methyl derivative, cyclization of which is now in progress. No antifungal activity of azacyclophane (1) to five types of funngi was observed by the disc method. Behaviors were investigated according to Irwin's method in ddY strain 5 week mice. As a result, writhing was observed during by the injection with the cyclic amine (1).

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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