Synthesis and Biological Activity of Strongly Fluorescent Tricyclic Analogues of Acyclovir and Ganciclovir

In search of strongly fluorescent tricyclic analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2), derivatives of the 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine system, several 6-[4-(acyloxy)phenyl], 6-[4-(acylamino)phenyl], and 6-[4-(phenoxycarbonyloxy)phenyl]-substituted TACV and TGCV analogues...

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Veröffentlicht in:	Journal of medicinal chemistry 2002-11, Vol.45 (23), p.5052-5057
Hauptverfasser:	Goslinski, Tomasz, Golankiewicz, Bozenna, De Clercq, Erik, Balzarini, Jan
Format:	Artikel
Sprache:	eng
Schlagworte:	Acyclovir - analogs & derivatives Acyclovir - chemical synthesis Acyclovir - chemistry Acyclovir - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Biological and medical sciences Cell Culture Techniques Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry Fluorescent Dyes - pharmacology Ganciclovir - analogs & derivatives Ganciclovir - chemical synthesis Ganciclovir - chemistry Ganciclovir - pharmacology Herpesvirus 1, Human - drug effects Herpesvirus 2, Human - drug effects Heterocyclic Compounds, 3-Ring - chemical synthesis Heterocyclic Compounds, 3-Ring - chemistry Heterocyclic Compounds, 3-Ring - pharmacology Humans Medical sciences Pharmacology. Drug treatments Purines - chemical synthesis Purines - chemistry Purines - pharmacology Structure-Activity Relationship
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Zusammenfassung:	In search of strongly fluorescent tricyclic analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2), derivatives of the 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine system, several 6-[4-(acyloxy)phenyl], 6-[4-(acylamino)phenyl], and 6-[4-(phenoxycarbonyloxy)phenyl]-substituted TACV and TGCV analogues were synthesized and evaluated for their activity against herpes simplex virus types 1 and 2 in cell culture. All TACV and TGCV analogues showed strong fluorescence (quantum yield of 30−65% vs 2-aminopurine 100%). The 6-[4-(phenoxycarbonyloxy)phenyl]-substituted compounds 11 and 19 displayed the best combination of the fluorescence and antiviral potency.
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm020827z