Nucleic acids components and their analogues. LXXXIII. Synthesis of 3-amino-2,5-dihydro-1,2,4-triazin-5-one (azaisocytosine) and its N-substituted derivatives

6-Aza-2‘-deoxyisocytidine: Synthesis, Properties of Oligonucleotides, and Base-Pair Stability Adjustment of DNA with Parallel Strand Orientation

“…Compounds 1a and 1b can also be synthesized by a convergent synthetic approach. The nucleobases 6-aza-5-methylisocytosine ( 7a ) and 6-azaisocytosine ( 7b ) were prepared from pyruvic acid and chloral, respectively, via cyclization of the corresponding guanylhydrazones with HMDS/TMSCl furnished 16a or 16b , which were used for the condensation with 2-deoxy-3,5-di- O -( p -toluoyl)-α- d - erythro -pentofuranosyl chloride ( 8 ) in CHCl 3 with CuI as a catalyst (Scheme ).…”

Synthesis and Biological Activity of Aminoguanidine and Diaminoguanidine Analogues of the Antidiabetic/Antiobesity Agent 3-Guanidinopropionic Acid

“…Compound 13 is available from commercial sources. Compounds 8 , 9 , 18 , 28 , 31 , and 32 21 were prepared according to literature procedures.…”

“…Tables 1-8 depict the analogues that were prepared and evaluated for this study. Compounds 8, 4 9, 5 and 18 6 were prepared according to literature procedures. Compound 13 is an item of commerce.…”

“…Alkylation of aminoguanidine with 2-bromoacetic acid gave 10. Saturation of the known triazinone 31 6 by catalytic hydrogenation in aqueous HCl gave the cyclic analogue 11. A heteroaromatic replacement of the aminoguanidine moiety was also investigated.…”

“…The solid was slurried in hot EtOAc (300 mL) to dissolve any sulfur related byproducts and triturated with hexane (200 mL) to afford 17.1 g of 99 (53%) as a white solid: mp 148-149 °C; 1 H NMR (CD3OD) δ 5.20 (s, 2 H), 7.30 (m, 5 H) remaining CH2 not observable; 13 C NMR (CD3OD) δ 54. 8, 68.7, 129.1, 129.2, 129.4, 137.1, 171.8, 185.3, 198.6; MS (FAB) m/z (rel intensity) 284 (M + H, 99), 567 (9), 566 (8), 392 (8), 362 (7), 361 (10), 360 (57), 285 (14), 284 (99), 92 (6), 91 (72). Anal.…”