Synthesis and anti-HBV activity of α-stereoisomer of aristeromycin based analogs

Dual active pyrimidine-based carbocyclic nucleoside derivatives: synthesis, and in silico and in vitro anti-diabetic and anti-microbial studies

“…To synthesize compounds 10a–c , the key building block intermediate, 6(b) was used along with C-4 substituted 8-aza-7-deaza purines 42,43 and the same protocol was followed and afford target compounds 10a–c (Table 1) (Scheme 1). In the 1 H-NMR spectrum of all the new compounds synthesized from intermediate, 6(b) , the characteristic 7-deaza (–CH–) proton signal was observed at δ 8.22 ppm.…”

“…1 H-NMR of compound 8a indicated singlet at d 8.69 ppm for Pyrimidine ring proton (proton between nitrogen's), the doublet with chemical shi value of d 8.37-8.36 ppm for pyrrole ring proton (proton adjacent to NH) and 7.68 ppm for alkene proton and the olen proton was seen in the down-eld region of d 7.68 ppm. The 13 To synthesize compounds 10a-c, the key building block intermediate, 6(b) was used along with C-4 substituted 8-aza-7deaza purines 42,43 and the same protocol was followed and afford target compounds 10a-c (Table 1) (Scheme 1). In the 1…”

Nucleobase coupling by Mitsunobu reaction towards nucleoside analogs

“…35 However, there are alcohols where MR coupling did not succeed, even when several reaction conditions were explored. Few such examples are reported in literature by Chen et al 36 during assembly of fluorinated acyclic nucleoside phosphonates containing cytosine and adenine, by Brémond et al 37 and Kasula et al 38 in an attempted synthesis of aristeromycin analogs embodying 6-chloropurine and 7-deazapurine moieties, respectively. Rosen et al 39 also failed the coupling of cytosine and 2-amino-6-chloropurine to mono-fluorinated cyclopropane sugar mimetics.…”

Synthesis of 4a‐Carba‐d‐lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α‐Mannosidases

“…[31][32][33][34] In analogy, the preparation of 4a-carba--D-lyxofuranose 14 was commenced from D-lyxose which was initially protected as lyxofuranose 7 according to recognized procedures (Scheme 1). [31][32][33][34] In analogy, the preparation of 4a-carba--D-lyxofuranose 14 was commenced from D-lyxose which was initially protected as lyxofuranose 7 according to recognized procedures (Scheme 1).…”

“…[35,36] Next, nucleophilic addition of vinylmagnesium bromide to an aldehyde group of an open-chain form of 7 afforded diastereomeric diols 8 in 3:1 ratio in almost quantitative yield (Scheme 1). Kasula et al [32] reported diastereoselective syn-hydrogenation of double bond in antipode of 13 on 10 % Pd-C with Na 2 CO 3 in EtOAc to give 4a-carba--L-lyxofuranose in 95 % yield. Major anti-isomer 8a was separated by column chromatography in 66 % yield, and was used optically pure in the following reaction sequence (Scheme 2).…”