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Summary Synthesis of 2,4-bis-(4-amidinophenyl)-6-methylpyrimidine 5 , 2,4-bis-[(4-imidazolin-2-yl)phenyl]-6-methylpyrimidine 6 , 2,4-bis[(4- N-i -propylamidino)phenyl]-6-methylpyrimidine 7, and 2,4-bis[(4- N -isopentylamidino)phenyl]-6-methylpyrimidine 8 starting from 4-bromobenzamidine and 4′-bromoacetophenone is reported. The synthesis of 2,4-bis-(4-amidinophenyl)-5-methylpyrimidine 12 and 2,4-bis-[(4-imidazolin-2-yl)phenyl]-5-methylpyrimidine 13 , also beginning with 4-bromobenzamidine and 4′-bromopropiophenone is described. A synthesis of 4,6-bis-(4-amidinophenyl)-2-methylpyrimidine 17 , 4,6-bis-[(4-imidazolin-2-yl)phenyl]-2-methylpyrimidine 18 , 4,6-bis[(4- N-i -propylamidino)phenyl]-2-methylpyrimidine 19 and 4,6-bis[(4- N-n -propylamidino)phenyl]-2-methylpyrimidine 20 starting from acetamidine and 1,3-bis(4-bromophenyl)propenone is reported. Compounds 5–7 and 17–20 all bind strongly to the minor groove of poly-dA-dT whereas 8, 12 and 13 bind less tightly as judged by their Δ T in values. A similar trend was noted for binding of these compounds to the 12-mer-d(CGCGAATTCGCG) 2 . Compounds 5, 7, and 17 are more active and less toxic than pentamidine at its effective dose when evaluated against Pneumocystis carinii pneumonia (PCP) in the immunosuppressed rat model. |
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