Synthesis of C-Glycosyl Thiazoles

Synthesis and antiviral activity of certain thiazole C-nucleosides

“…These glycosylthiocarboxamides were utilized as the precursors for the synthesis of 2-D-ribofuranosylthiazole-4-carboxamide and 2-/3-D-ribofuranosylthiazole- 5-carboxamide (23). The structural modification of 2-lS-D-ribofuranosylthiazole-4-carboxamide (12) into 2-(2,3,-5-tri-0-acetyl-d-D-ribofuranosyl)thiazole-4-carboxamide (15), 2-j3-D-ribofuranosylthiazole-4-thiocarboxamide (17), and 2-(5-deoxy-d-D-ribofuranosyl)thiazole-4-carboxamide (19) is also described. These thiazole nucleosides were tested for in vitro activity against type 1 herpes virus, type 3 parainfluenza virus, and type 13 rhinovirus and an in vivo experiment was run against parainfluenza virus.…”

The Chemistry of C-Nucleosides

“…(192) All others in Fig. 4 (193) in more than 80% yield. When 231 was treated with ethyl bromopyruvate in pyridine, the p-C-nucleoside 232 was obtained as the major product (42%) along with the a isomer 233 (22%) and the furan derivative 234 (6.9%).…”

Synthesis of Nonhydrolyzable Analogues of Thiazole-4-carboxamide and Benzamide Adenine Dinucleotide Containing Fluorine Atom at the C2‘ of Adenine Nucleoside: Induction of K562 Differentiation and Inosine Monophosphate Dehydrogenase Inhibitory Activity

“…Aromatization of the tiazofurin sugar was reported to occur easily under basic condition. 12 However, similar reaction of 24 with the more acidic tris(tetrabutylammonium) salt of difluoromethylenebis(phosphonic acid) afforded the desired product 25. We reported earlier that the coupling of 25 with 2′-deoxy-2′-fluoroadenosine gave, after deprotection, the desired β-CF 2 -TAD analogue in 4.5% yield.…”

“…Pyridine was evaporated in vacuo; the residue was resuspended in water (5 mL), extracted with ethyl ether to remove unreacted DCC, and filtered to remove dicyclohexylurea. After HPLC purification, compound 23 (78 mg, 79%) was obtained as the bis(triethylammonium) salt: 1 (12). Compound 23 (78 mg, 0.08 mmol, bis(triethylammonium) salt) was deprotected by treatment with Dowex 50WX8 resin (H + form, 0.5 mL of the resin) in water solution (2 mL) for 2 h at 50 °C and then for 24 h at room temperature.…”

“…6 In an effort to improve hydrolytic stability and enhance membrane permeability of the fluorinated pyrophosphate analogue In addition to the preparation and characterization of the tiazofurin conjugates, we have in previous work also studied a nonhydrolyzable analogue (β-CH 2 -BAD, 11) 7 of benzamide adenine dinucleotide (BAD, 10) 8 and found that 11 was a potent inhibitor of IMPDH. 7 Prompted by the activity of several of the fluorinated derivatives of TAD, we synthesized the 2′-fluoro ara analogue of the benzamide derivative (12). We have determined the activity of all these compounds as inhibitors of IMPDH and as inducers of K562 cell differentiation.…”