Six fluoroquinolone ribonucleosides were synthesized by using microwave irradiation starting from fluoroanilines. In most cases the microwave application proved superior in time and yield, especially the one step decarboxylation of the carboxyquinolone esters3a-3cand the Vorbrüggen glycosylation. The former led to the new type of fluoroquinolone ribosides8a-8c. Compound8cin the crystal structure showed C3'-endo and anti conformation. The nucleosides were examined, but found inactive against the replication of HIV-1(IIIB) in cell culture, while they were toxic for the cells at a 50% cytotoxic concentration ranging from 31 to >125 μg/ml. But measurements of the inhibitory effects against HIV-1 integrase enzymatic activity showed an interesting activity for compound8c.
During the last decades the nucleoside synthesis has proven to be important. The modified silyl-Hilbert-Johnson nucleoside synthesis modified by Vorbrüggen is one of the most often used methods. We have studied N-glycosilation of modifieded heterocyclic bases by Vorbrüggen method with microwave irradiation and we were able to shorten the reaction time and obtain higher yields. The method was demonstrated by fluoroquinolone and purine.
Nucleic acids U 0700Microwave-Assisted Synthesis of Fluoroquinolones and Their Nucleosides as Inhibitors of HIV Integrase. -Slightly modified known methods and the use of microwave irradiation lead to improved results in the synthesis of 6 fluoroquinolone ribonucleosides (I) and (II). Pharmacological studies reveal positive effects in the case of (IIc). -(ADAMS, M. M.; BATS, J. W.; NIKOLAUS, N. V.; WITVROUW, M.; DEBYSER, Z.; ENGELS*, J. W.; Collect. Czech. Chem. Commun. 71 (2006) 7, 978-990; Inst. Org. Chem. Chem. Biol., Johann Wolfgang Goethe-Univ., D-60439 Frankfurt/M., Germany; Eng.) -S. Adam 01-205
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