Synthesis and fluorescent properties of 6-(4-biphenylyl)-3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine analogues of acyclovir and ganciclovir |
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Authors: | Goslinski Tomasz Wenska Grazyna Golankiewicz Bozenna Balzarini Jan De Clercq Erik |
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Affiliation: | Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań, Poland. |
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Abstract: | Tricyclic (T) analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2) carrying the 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine system [i.e., 6-(4-BrPh)TACV, 5 and 6-(4-BrPh)TGCV, 6] were transformed into 6-[(4'-R2)-4-biphenylyl] derivatives of TACV (7-9) and TGCV (10-12) by Suzuki cross coupling with 4-substituted phenylboronic acids. Compound 11 (R2 = CH2OH) showed a high (approximately 1000) selectivity index against herpes simplex virus type 1 (HSV-1) together with advantageous fluorescence properties (emission in visible region, little overlap with absorption and moderate intensity). |
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