A versatile method for the solid-phase synthesis of 2-aminoquinazoline-based derivatives, 3-substituted-3,4-dihydroquinazolin-2-amines and imidazoquinazolines, has been developed. They were obtained by treating the amino group of polymer-linked amino acids with 2-nitrobenzaldehyde followed by reduction of the nitro group to an amine. Cyclization of the resulting immobilized intermediates with cyanogen bromide followed by acidic/basic cleavage yielded the desired quinazoline-based compounds in high yields and purities.
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[structure: see text] We have previously described a system of 2-aminoquinoline- and 2-aminoquinazoline-based C-deoxynucleosides (TRIPsides) that are designed to be incorporated into oligomers that can specifically bind in the major groove via Hoogsteen base pairing to any sequence of native DNA. The four TRIPsides are termed antiGC, antiCG, antiTA, and antiAT with respect to the Watson-Crick base pair targets that they bind. The first three TRIPsides have been prepared, characterized, and shown to form stable and sequence-specific triplexes.
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A versatile method for the solid-phase synthesis of 2-aminoquinazoline-based derivatives, 3-substituted-3,4-dihydroquinazolin-2-amines and imidazoquinazolines, has been developed. They were obtained by treating the amino group of polymer-linked amino acids with 2-nitrobenzaldehyde followed by reduction of the nitro group to an amine. Cyclization of the resulting immobilized intermediates with cyanogen bromide followed by acidic/basic cleavage yielded the desired quinazoline-based compounds in high yields and purities.
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