反応式
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH2:9][NH2:10].O([C:18]1[C:19]2[C:24]([N:25]=[C:26]3[C:31]=1[CH:30]=[CH:29][CH:28]=[CH:27]3)=[CH:23][CH:22]=[CH:21][CH:20]=2)C1C=CC=CC=1>>[CH:20]1[C:19]2[C:24](=[N:25][C:26]3[C:31]([CH:18]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:22][CH:21]=1.[CH:20]1[C:19]2[C:24](=[N:25][C:26]3[C:31]([CH:18]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:22][CH:21]=1.[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH2:9][NH2:10]参加物
実験手順
The scheme for directing nucleic acids to certain sites of the body is based upon the intercalation of a ligand which interacts with a cell surface component into the double stranded DNA. A procedure for selective N4 -acylation of spermidine, using N1,N8 -bis(t-butoxycarbonyl) spermidine as starting material, has been reported. R. J. Bergeron et al., Synthesis (1982) 689-692. We have used this procedure (FIG. 8) to link the acid functionalized galactosyl derivatives 9 (n=1) and 9' (n=4) to the secondary amino group of N1,N8 -tBOC-protected spermidine (15) and the resulting galactosylated spermidines 17 and 17' were, after deprotection, further alkylated with 9-phenoxyacridine by a standard chemical procedure to transform them into bis-intercalator compounds 21 and 21'. The synthesis of the carboxylic acid functionalized galactosyl derivatives is detailed (J. Haensler et al., Biochim Biophys Acta (1988) 946:95-105) and is easily applicable to a wide range of carbohydrate ligands (M. M. Ponpipom et al., J Med Chem (1981) 24:1388-1395). The title compounds were obtained in an overall yield of 30% and the NMR and mass spectrometry data are consistent with the proposed structure.
後処理
- customBergeron et al., Synthesis (1982) 689-692
出典と根拠
- ORDレコード
- ord-e05b122b69024e25b851102b0f95979a
- 出典データセット
- uspto-grants-1999_09
- 特許番号
- US05955365
関連ノート
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