1-Substituted 2′-deoxyinosine analogues

2′‐O‐Alkyl Derivatives and 5′‐Analogues of 5‐Aminoimidazole‐4‐carboxamide‐1‐β‐D‐ribofuranoside (AICAR) as Potential Hsp90 Inhibitors

“…The synthesis of AICAR from N 1 -substituted inosine is in fact nowadays utilized and preferred over other older protocols [14] due to its higher yields and easier isolation procedures. [15] According to the literature, when the N 1 -position of the hypoxanthine ring is substituted with a 2,4-dinitrophenyl [16] or a (2-methoxyethoxy)methyl (MEM) [17] group, treatment with alkali, aqueous NaOH or ethylenediamine, respectively, allows the simultaneous opening of the pyrimidine ring and removal of the N 1 substituent to afford AICAR. The first time we tackled the synthesis of these derivatives we explored these two different approaches.…”

Synthesis of a New N1-Pentyl Analogue of Cyclic Inosine Diphosphate Ribose (cIDPR) as a Stable Potential Mimic of Cyclic ADP Ribose (cADPR)

“…For the N 1 -alkylation of inosine we utilized the already described procedure based on the reaction of N 1 -(2,4-dinitrophenyl)inosine with alkylamine. [15] Thus, acetylation of 2Ј,3Ј-isopropylideneinosine (8) with Ac 2 O in pyridine led to the 5Ј-O-acetyl derivative 9 [16] which was, in turn, converted into the N 1 -(2,4-dinitrophenyl) derivative 10 by reaction with 2,4-dinitrochlorobenzene and K 2 CO 3 in DMF (90% yields). Compound 10 was obtained as a 1:1 mixture of atropisomers at the N-1 position.…”

Unambiguous structural elucidation of base‐modified purine nucleosides using NMR

“…In the literature, these two 13 www.interscience.wiley.com/journal/mrc assigned and there are inconsistent assignments of 1 H peaks and 13 C peaks for the 2-and 8-positions. [17] In some cases, 2-H and 2-C were assigned to resonances at higher δ-values than 8-H and 8-C. [18,19] Assignment of the remaining purine carbons (i.e. 4-C, 5-C and 6-C) is more challenging as these carbon atoms do not bear any protons; thus, HMQC is of no use in this instance.…”

“…N1-(2,4-dinitrophenyl)-2 -deoxyinosine (4) was synthesized based on a published protocol [18] ; [1-15 N]-2 -deoxyinosine (5) is prepared using a modified protocol. [33] N1-methyl-2 -deoxyinosine (6), N1-(2-aminoethyl)-2 -deoxyinosine (7) and N1-hydroxy-2 -deoxyinosine (8) were prepared by treatment of 4, respectively with methylamine (40% aqueous solution), ethylenediamine or hydroxylamine (from hydroxylamine hydrochloride and KOH) using the procedures described in our previous paper.…”