1994 Fiscal Year Final Research Report Summary
Reactivity of imidazole moiety of fused aromatic ring for ionic and radical reaction species : Molecular stady for DNA damage
| Project/Area Number |
05671763
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Nagoya City University |
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Principal Investigator |
KOHDA Kohfuku FAC.OF PHARMACEUTICAL SCI.NAGOYA CITY UNIVERSITY ASSOCIATE PROFESSOR, 薬学部, 助教授 (60124286)
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| Co-Investigator(Kenkyū-buntansha) |
KAIYA Toyo FAC.OF PHARMACEUTICAL SCI.NAGOYA CITY UNIVERSITY ASISTANT PROFESSOR, 薬学部, 講師 (10080201)
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| Project Period (FY) |
1993 – 1994
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| Keywords | q-ethylguanine / l-methylbenzimidazole / electrophilic amination / N-aminoguanine / N-amino-l-methylbenzimidazole |
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| Research Abstract |
Electrophilic amination of four 9-ethylguanine derivatives (1a-d) and seven 1-methylbenzimidazole derivatives (4a-g) with 2,4-dinitrophenoxyamine (DNPA) was carried out in DMF.N-amination proceeded at the imidazole moiety of these compounds with pKa's of more than 3.2 (1a, 1b, 4a, 4b, 4c, 4d). Treatment of these N-aminated derivatives (2a-b, 5a-d) with 0.1 N NaOH gave different results depending on their structures. In the guanine series, 9-ethyl-8-oxoguanine derivatives (3a, 3b)were obtained from N-aminated compounds (2a, 2b). In the benzimidazole series, no reaction proceeded with N-aminated compounds of 5a and 5b, whereas the benzo [1,2,4] triazine derivatives (6c, 6d) were obtained from N-aminated compounds (5c, 5d) , respectivery. It is not clear why the reactivity was different between purines (2a, 2b) and benzimidazoles (5c, 5d) although these have similar pKa values.
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