A versatile route to C-6 arylmethyl-functionalized S-DABO and related analogues.
Since their discovery in 1992, 3,4-dihydro-2-alkoxy-6-benzyl-4-oxypyrimidines (DABOs) have been subjected to many structural modifications in order to obtain better non-nucleoside reverse transcriptase inhibitors (NNRTIs) for the treatment of AIDS. Herein, we report a straightforward and versatile route for the synthesis of novel C-6 arylmethyl-functionalized S-DABO, a poorly explored class of derivatives. Finally, biological evaluation of the synthesized derivatives led to the identification of a promising anti-HIV-1 lead compound.
Radi
Marco
M
Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, Via Alcide de Gasperi 2, I-53100, Siena, Italy.
Contemori
Lorenzo
L
Castagnolo
Daniele
D
Spinosa
Raffaella
R
Esté
José A
JA
Massa
Silvio
S
Botta
Maurizio
M
D000163:Acquired Immunodeficiency Syndrome / Q000188:drug therapy; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D019380:Anti-HIV Agents; D011743:Pyrimidines; D018894:Reverse Transcriptase Inhibitors