Ring‐Open Analogues of Adenine Nucleoside. Aminoacyl Derivatives of Cyclo‐ and Acyclo‐Nucleosides

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Abstract
The synthesis of acyclic analogues of ribo‐ and deoxyribonucleosides is described. These compounds (Table 3) are both poor substrates and poor inhibitors of adenosine deaminase. The synthesis of dinucleotides from these analogues is also described, and the activity along with the inhibitory properties of some of them are studied against deaminase enzyme. These nucleotides are resistant to degradation by phosphodiesterases. HCl impregnated on silica gel is an excellent reagent for the preparation of the chloromethyl ether precursors of acyclo‐nucleosides. A general and rapid procedure is developed for the preparation and isolation of the 5′‐aminoacyl derivatives of robo‐ and arabinonucleosides. Quinoline has a marked effect on aminoacylations without racemization. Compounds 35a, b possess remarkable antiviral effects in vitro. A procedure is also developed for the conversion of acyclo‐ribonucliosides 13e, f to acyclo‐deoxyribonucleosides 11e, f.

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