Abstract
Marine secondary metabolites with a purine motif in their structure are presented in this review. The alkylpurines are grouped according to the size of the alkyl substituents and their location on the purine ring. Aspects related to the marine source, chemical structure and biological properties are considered together with synthetic approaches towards the natural products and bioactive analogues. This review contributes to studies of structure–activity relationships for these metabolites and highlights the potential of the sea as a source of new lead compounds in diverse therapeutic fields.
Highlights
Natural products play a highly significant role in drug discovery and development processes.It is well known that a high proportion of commercial drugs came from natural compounds isolated from plants and terrestrial organisms [1]
A and B using similar methodology (Scheme 12), starting from D-ribose, 160, through the 2-methyl triacetate 161 but using directly the corresponding unprotected nucleobase. This procedure has been improved by the same authors [145] and applied to the synthesis of several analogues (162) modified at the nucleobase in order to evaluate their cytotoxicity, which could not be evaluated previously for trachycladine B, 141, because of the small amounts isolated from its natural source
1. containing a purine moiety alkylated at any nitrogen atom of the Marine secondary metabolites
Summary
Natural products play a highly significant role in drug discovery and development processes. It is well known that a high proportion of commercial drugs came from natural compounds isolated from plants and terrestrial organisms [1] In this sense, the sea is a relatively unexplored source of natural products, which offers a significant potential for the discovery of molecules with relevance in different therapeutic areas. Purines are the most widely naturally occurring heterocycles and exist as free bases, nucleosides, nucleotides, polynucleotides, or structural fragments of vitamins [4], but we will focus our attention on those formed by a purine unit substituted with different alkyl chains at any nitrogen atom of the purine These compounds have been organized according to the size and nature of the alkyl chain, ranging from simple methyl groups to larger side chains. Aspects related to the marine source, chemical structure and biological properties of marine alkylpurines are considered together with some synthetic approaches towards the natural products and/or their bioactive analogues
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