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The synthesis of a series of pyrazine analogues of the anti-herpes compound, acyclovir is described. These syntheses were accomplished by various methods: in the presence of a Lewis acid or NaH for hydroxyethoxymethyl and hydroxybutyl groups or by sequential oxidation/reduction of l-β-D-ribofuranosyl)-2-pyrazinones for 2′,3′-acyclonucleosides. Antiviral (HSV-1, CMV, Cox B4, HIV-1) properties of these compounds were determined.

Novel porphyrins bearing nitro groups and glucosyl moieties were synthesized. The antibacterial activity of these compounds on Escherichia coli and Staphylococcus aureus is described. Results reveal that their photocytotoxicity is markedly dependent on the nature, the number and the linking position of the glycosyl moieties and nitro groups controlling their amphiphilic characters.

To obtain molecules that can target malignant cells, two series of new meso glucosylporphyrins bearing amino acid residues are synthesized in four steps. The first series contained n meso glycosyl moieties and (4 − n) alanyl groups on the ortho or para positions of the meso phenyl. In the second series, the carbohydrate moiety is separated from the aryl substituent by a serine unit. Starting from p- or o-nitrobenzaldehyde, p- or o-acetylbenzaldehyde or -tolualdehyde, and pyrrole, the glycosylnitrophenylporphyrins 3−6 and tritolylporphyrins 8a,b are synthesized under optimized conditions tailored from Lindsey's method. The nitro function is then reduced and N-Fmoc-l-alanine or acetylglycosylated N-Fmoc-serine are coupled on the amino function. A detailed 1H and 13C NMR study allows complete structural elucidation. The UV−visible fluorescence and MALDI mass spectra are presented. Compounds 19−22 produced 1O2, and photocytotoxicities against the K562 leukemia cell line are compared to hematoporphyrin. As a r...

The aim of this work is the synthesis of a new family of glycosylated porphyrins in which the sugar moieties are linked to the tetrapyrrole ring by a thioglycosidic bond. Two series have been designed. The first one corresponds to meso-aryl porphyrin derivatives. The second one has been obtained from protoporphyrin IX derivatization. Aryl-porphyrins were prepared from tristolyl o- and p-hydroxyporphyrins followed by bromoallylation and thioglycosylation with peracetylated S-glucose, mannose and galactose and deprotection. The other series has been synthesized from protoporphyrin IX dimethylester with a regioselective glycosylation of terminal alkenyl carbon. The UV-visible, NMR and MALDI mass spectra are presented. Photocytotoxicities of the synthesized compounds against K562 chronic leukaemia cell line has been evaluated.

The synthesis of a polycyclic heterocyclic ring system compound, ethyl 7-hydroxy-4-oxo-2-phenyl-4,5-dihydro-3H-benzo[6,7]cyclohepta[1,2-d]pyrimidine-6-carboxylate was carried out by condensation of benzamidine on diethyl 5,9-dihydroxy-7H-benzo[a]cycloheptene-6,8-dicarboxylate, after opening and then closure of the seven membered ring.

The synthesis of a new family of D4T analogues is described to study the influence of pyrazinone base on antiretroviral power. Substitution of 3H by methyl or n-decyl increases the lipophilic character and may facilitate diffusion across cell membranes. The compounds were characterized by (1)H NMR and infrared spectroscopy. Antiviral (HIV-1) properties of these compounds were examined.

Thumbnail image of graphical abstract A sugary treat: Here we report the great efficiency of sugar-based-surfactant combined catalysts for conducting selective base-catalyzed organic reactions in glycerol. Close control of the reaction selectivity was successfully obtained owing to the formation of catalytic hydrophobic pockets in glycerol (see figure). The advantages of our catalytic processes and its similarities with catalysis in water are also highlighted.

By using activated carbon fiber (ACF) as solid acid promoter, we display a new system for solvent free O- and N-glycosylation, with a simple process which takes place in a drying oven; this method has been applied to the synthesis of sterol and triterpene O-glycosides (saponin analogues), as well as nucleoside analogues.