ChemInform Abstract: Synthesis, Lipophilicity and Anti‐HIV Activity of a New Brominated Analogue of Zidovudine.

Abstract

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Biological evaluation and molecular modelling of didanosine derivatives

“…[19][20][21][22][23][24][25][26][27] The lipophilic character of the side chains at the 5´-O position should influence their ability to cross the cell membrane by passive diffusion, which is a key feature in the absence of an active nucleoside transport system. [22][23][24][28][29] As stated by Parang et al, 20 more selective compounds can be designed by using the strategy of 5'-Ocarbonates substitution. Although the clinical application of these approaches remains unknown, they hold the promise of becoming an important tool in the treatment of HIV infection and its related consequences.…”

“…Recently, we synthesized and evaluated the anti-HIV activity of carbonate prodrugs of lamivudine (3TC) with the aim of generating 3TC derivatives that were able to suppress HIV-replication more efficiently than its parent drug, with some promising results being reported. 30 Therefore, as part of our ongoing efforts to search novel antiviral agents, 28,[30][31][32][33][34] we also used the 5'-O-carbonate substitution strategy to link the aliphatic alcohols on the 5´-O position of DDI in order to enhance their lipophilicity, to facilitate their diffusion through the cell membrane independently of the nucleoside transport system, and to improve the in vitro anti-HIV activity of DDI. [35][36]…”