Nucleocyclitols. Synthesis of 3-(adenin-9-yl)-3-deoxy-1,5,6-tri-O-(methylsulfonyl)-muco-inositol

Conformationally Restricted Nucleocyclitols: a Study into their Conformational Preferences and Supramolecular Architecture in the Solid State

“…Interest in the synthesis of nucleocyclitols, a term coined by Cadenas for hydrid molecules obtained by condensing cyclitols with purine or pyrimidine bases, largely stemmed as an offshoot from the efforts towards the development of novel nucleoside analogues as potential antitumor, antiviral or antibiotic agents. Devoid of an endocyclic oxygen and thus the “oside” structure, nucleocyclitols present a base‐cyclitol C–N bond which, unlike that present in nucleosides, is stable towards both chemical and enzymatic hydrolysis, a property perceived as a definite vantage point for in vivo testing 8a. However, literature reports on the bioactivity profile of nucleocyclitols are rather sparse, barring a study by Carceller and Cadenas, which revealed that 3‐(adenin‐9‐yl)‐3‐deoxy‐1,5,6‐tri‐ O ‐(methylsulfonyl)‐ muco ‐inositol exhibited cytokinin‐like activity in promoting cell proliferation in soybean cotyledon callus tissue, cell expansion in excised radish cotyledons, and delay of senescence in detached leaves 8b.…”

Action of Nitrogenated and Sulfonylated Inositol Derivatives upon the Proliferation in vitro of Normal Mouse Cells and Tumor Mouse Cells

“…5: l,5-dichloro-6-N-bis(2-chloroethyl)aminol',5',6/-tridcoxy-2,3,4-tri-0-(methylsulfonyl)mucoinositol (DEI) [13]; No. 6: l,5,6-tri-0-(methylsulfonyl)mucoinositol [11].…”

“…Their structures are shown in figure 1: No. 1:3'-(6-methylmercaptopurine-9-yl)-3'-deoxyl',5',6'-tri-0-(mcthylsulfonyl)mucoinositol (MPI) [ 10]; [11]; No. 5: l,5-dichloro-6-N-bis(2-chloroethyl)aminol',5',6/-tridcoxy-2,3,4-tri-0-(methylsulfonyl)mucoinositol (DEI) [13]; No.…”