Synthesis and fluorescent properties of the tricyclic analogues of acyclovir linked with nitrogen hetbrocyclic units.
Tricyclic (T, 3,9-dihydro-9-oxo-SH-imidazo[g2-c]purine) analogues of acyclovir (ACV, 1), substituted in the 6 position with pyrid-4-yl, 4-(pyrid-4'-yl)Ph, 4-(pyrimidin-5-yl)Ph and 4-(thiazol-2'-yl)Ph units were synthesized. For the synthesis of the heteroarylphenyl derivatives, a convenient general route was developed, ie., Suzuki cross-coupling between protected 6-(4-dihydroxyborylphenyl) TACV and easily available bromoheterocycles. Fluorescent properties of newly synthesized TACV aoalogues strongly depend on the nature of a solvent. This sensitivity of fluorescence makes the compounds promising probes of H-bonding in the environment.
Goslinski
Tomasz
T
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznan, Poland.
Januszczyk
Piotr
P
Wenska
Grazyna
G
Golankiewicz
Bozenna
B
De Clercq
Erik
E
Balzarini
Jan
J
D000042:Absorption; D000212:Acyclovir / Q000138:chemical synthesis* / Q000494:pharmacology*; D000963:Antimetabolites / Q000494:pharmacology*; D000998:Antiviral Agents / Q000737:chemistry / Q000494:pharmacology; D003432:Cross-Linking Reagents / Q000494:pharmacology; D005456:Fluorescent Dyes / Q000494:pharmacology; D006860:Hydrogen Bonding; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013050:Spectrometry, Fluorescence / Q000379:methods*
D000963:Antimetabolites; D000998:Antiviral Agents; D003432:Cross-Linking Reagents; D005456:Fluorescent Dyes; D012997:Solvents; D009584:Nitrogen; D000212:Acyclovir