Synthesis of Cyclic and Acyclic Nucleoside Phosphonates and Sulfonamides Derived from 6-(Thiophen-2-yl)-7-fluoro-7-deazapurine

Abstract

Ribonuclosides derived from 6-hetaryl-7-dezapurines are potent cytostatics, but their mechanism of action is unknown. Here we designed and synthesized a series of cyclic and acyclic nucleoside phosphonates, as well as carboxy, cyano, sulfo, and sulfonamide acyclic analogues derived from 6-thiophen-2-yl-7-deazapurine and 7-fluoro-6-thiophen-2-yl-7-deazapurine as ribonucleoside monophosphate mimics.

None of these analogues exerted significant cytotoxic and antiviral activity.

Keywords

• 7-deazapurine
• nucleoside phosphonates
• structure-activity relationships
• synthetic methods
• sulfonamides