Synthesis, conformational analysis and antimicrobial activity of 10-benzyl-1,2,4-triazolo[4,3-b]1,2,4-triazino[5,6-b]indole acyclo C-nucleoside analogs.

Condensation of 5-benzyl-3-hydrazino-1,2,4-triazino[5,6-b]indole with various sugar aldoses or ketoses gave the corresponding sugar hydrazones as single geometrical isomer or exist in E/Z tautomeric isomers. The hydrazones underwent heterocyclization with Fe(Ш)Cl3 to give the N2-adduct acyclo C-nucleosides: 3-(alditol-1yl)-10-benzyl-1,2,4-triazolo[4,3-b]1,2,4-triazino[5,6-b]indoles rather than the N4-adduct: 10-(alditol-1-yl)-3-benzyl-1,2,4-triazolo[3,4-c]1,2,4-triazino[5,6-b] indoles on the basis of chemical and UV spectral proofs. Conformational analysis of their polyacetates were studied. The new acyclo C-nucleosides were evaluated for antimicrobial activity.

Synthesis and Antimicrobial Activity of 1,3,4-Oxadiazoline, 1,3-Thiazolidine, and 1,2,4-Triazoline Double-Tailed Acyclo C-Nucleosides.

The condensation products of terphthaloyl bishydrazide with two equivalents of various monosaccharide aldoses were found to have a bis(sugarhydrazone) form or bis-glycosylhydrazide structure or coexist in tautomeric equilibrium depending on the sugar configuration. The condensation products were substantially utilized as 3-acetyl-1,3,4-oxadiazoline, 1,3-thiazolidine, and 4-amino-1,2,4-triazoline double-tailed acyclo C-nucleosides synthons. The preliminary antimicrobial activities of representative examples of the prepared compounds were evaluated.

One pot synthesis of new cross-linked chitosan-Schiff' base: Characterization, and anti-proliferative activities.

Four novel chitosan hydrogels were successfully synthesized through the cross-linking reaction of chitosan with different concentrations of ethyl 5-(3,5-dihydroxy-1,4-dioxan-2-yl)-2-methylfuran-3-carboxylate. Their structures were confirmed by Fourier transform infrared spectroscopy (FT-IR), 13C Cross polarization magic angle spinning nuclear magnetic resonance spectroscopy (CP/MAS 13C NMR), ultraviolet-visible spectroscopy, thermogravimetric analysis (TGA, DTA), and X-ray diffraction (XRD). Cytotoxicity on hepatocellular carcinoma (HepG-2) cell line and a normal African green monkey kidney (Vero) cell line were studied using the MTT assay. The resultant hydrogels showed a good inhibitory effect comparing to the un-modified parent; the hydrogels with the lowest degree cross-linking (0.125 and 0.25 mol cross-linker per one chitosan residue) showed potent anticancer activity in the HepG2 cells with IC50 of 57.9 and 80.9 µg/ml, respectively. These results show that the newly synthesized cross-linked chitosan derivatives demonstrated more selectivity to the HepG2 than the Vero cells, indicating its potential for Investigation in the cure of hepatocellular carcinoma.

Synthesis and characterization of chitosan-pyrazoloquinoxaline Schiff bases for Cr (VI) removal from wastewater.

Two novel chitosan Schiff bases namely chitosan pyrazolo[3,4-b]quinoxaline Schiff base (Ch-PQ1) and chitosan phenyl-1H-pyrazolo[3,4-b]quinoxaline Schiff base (Ch-PQ2) were synthesized as a modification of chitosan in order to increase its ability in heavy metal removal from wastewater. Their structures were characterized by FT-IR spectroscopy, TGA analysis and X-ray diffraction. They were tested for the removal of hexavalent chromium from synthetic samples. In addition pH conditions, polymer dosage, Cr (VI) initial concentration and contact time were studied as a key factor for the adsorption process. Kinetic studies of the removal process were also clarified. Furthermore, experimental equilibrium data were fitted to Langmuir and Freundlich adsorption isotherms. Both chitosan Schiff bases showed high removal efficiency, the result indicated that Cr (VI) removal using Ch-PQ1 and Ch-PQ2 was 96.4% and 98.8% respectively.

First synthesis of double headed 1,3,4-oxadiazino[6,5-b]indole acyclo C-nucleosides.

Condensation of 1,3-dihydro-2,3-dioxo-2H-indoles (la-c) with galactaric acid bis hydrazide (2) gave the corresponding galactaric acid bis[2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)hydrazides] (3a-c). Acetylation of the latter compounds with acetic anhydride in the presence of pyridine at ambient temperature gave the 2,3,4,5-tetra-O-acetylgalactaric acid bis[2-(1,2-dihydro-2-oxo-1-substituted-3H-indol-3-ylidene)hydrazides] (4b-d). Heterocyclization of the tetra-O-acetates 4b-d by heating with thionyl chloride afforded the double headed acyclo C-nucleosides: 1,2,3,4-tetra-O-acetyl- 1,4-bis[9-substituted-1,3,4-oxadiazino[6,5-b]indol-2-yl-1-ium]-galacto-tetritol dichlorides (5b-d). Structures of the prepared compounds were elucidated from their spectral properties.

Synthesis of double headed imidazoline acyclo C-nucleosides: 1,4-bis[1-amino-5-oxo-4-substituted(imidazolin-2-yl)]galacto-tetritols.

Condensation of 2,3,4,5-tetra-O-acetyl-galactaroyl dichloride (1) with two equivalents of the alpha-amino esters 2a-c gave the corresponding 2,3,4,5-tetra-O-acetyl-galactaric acid diamides 3a-c. Heterocyclization of 3a-c by heating with hydrazine hydrate took place with concomitant de-O-acetylation of the polyacetoxyalkyl chain to give 1,4-bis[1-amino-5-oxo-4-substituted(imidazolin-2-yl)] galacto-tetritols (5a-c) and not the theoretically possible 1,2,4-triazinones 4 as indicated by spectral data. Compounds 5a-c readily reacted with p-nitrobenzaldehyde to give the corresponding p-nitrobenzylideneamino derivatives 6a-c. Acetylation of 5a-c afforded the 2,3,4,5-tetra-O-acetyl-1,4-bis[1-acetamido-5-oxo-4-substituted(imidazolin-2-yl)]galacto-tetritols (7a,b,d). De-O-acetylation of 7a,b,d gave 1,4-bis[1-acetamido-5-oxo-4-substituted (imidazolin-2-yl)]galacto-tetritols (8a-c).