Synthesis and complementary complex formation properties of oligonucleotides covalently linked to new stabilizing agents.

Interaction of Oligonucleotides Conjugated to Substituted Chromones and Coumarins with HIV-1 Reverse Transcriptase

“…Pyranone compounds (Fig. 1 ) and ODNs and their derivatives were synthesized as already described (Balbi et al, 1994(Balbi et al, , 1997Sottofattori et al, 1995).…”

“…Because such compounds significantly increased the stability of complexes formed by complementary ODNs in solution (Balbi et al, 1994(Balbi et al, , 1997, it was reasonable to suppose that the observed increase in primer affinity was due to the intercalating properties of these compounds. Although we have already shown that the ethidium group had an important effect on the interaction between RT and primer (Khodyreva et al, 1993), its influence was markedly lower than that produced by the two new modifying groups.…”

Facile solvent-free one-pot synthesis of pyranobenzopyrans and their derivatives

“…Pyranobenzopyrans and its derivatives are reported to possess various biological activities such as antibacterial, antifungal, CNS depressant, antiviral, ulcer inhibitor, etc. [16][17][18][19][20][21][22] Suksdorfin and DCK which contain pyranobenzopyran moiety are known to be potent anti-HIV agents. 18 We therefore would like to report on a simple and efficient protocol for the synthesis of substituted pyranobenzopyran derivatives.…”

Amine Exchange and Unexpected Ring-Opening Reactions of Pyranone Derivatives: Synthesis of 3-Amino-Substituted Oxonaphthopyran-carbaldehydes and Tetrahydropyrimidinethanones as New Potential Oligonucleotide Stabilization Agents

“…± While developing new strategies to synthesize chromone derivatives, which can be linked to oligonucleotides to form conjugates with enhanced stabilization ability [1], we exploited the peculiar behavior of 3-nitrochromones, which can be summarized as follows: a) 2-(dialkylamino)chromones 1 undergo amine exchange when treated with mono-or diamines if position 2 is activated from a suitable substituent in position 3 [2]; b) the nitro group in position 3 can be displaced by an amino group (2 and 3) or, unexpectedly, by a cyano group (see 4) [2]. We took advantage of the above behavior by developing, inter alia, simple synthetic pathways to 2-[(3-aminoalkyl)amino] [1]benzopyran-4(4H)-one derivatives 5. These compounds, which are able to stabilize the complementary oligonucleotide complexes [3], have also demonstrated the ability to interact and inhibit HIV-1 reverse transcriptase (RT) [4] [5].…”

“…Analogously to the preparation of 6, 0.2 g (0.75 mmol) of 2-(dimethylamino)-8-isopropyl-5-methyl-4-oxo-4H- [1]benzopyran-3-carbaldehyde 16 and propane-1,3-diamine (0.63 ml, 7.5 mmol) in toluene (5 ml) was heated at 1108 for 3 h. After cooling, the yellow precipitate was filtered off and crystallized from AcOEt (0.12 g, 58%). 1-Oxo-3-(propylamino)-1H-naphtho[2,1-b]pyran-2-carbaldehyde (12).…”