Synthesis of Some Purine Carbocyclic Isosteres of 2′,3′-Dideoxy-3′-C-Hydroxymethyl Nucleosides as Potential Inhibitors of HIV

Effect of terminal 3′-hydroxymethyl modification of an RNA primer on nonenzymatic primer extension

“…1). Several previous reports have described the synthesis of nucleotide analogs with an extended sugar phosphate backbone, typically beginning with a modified abasic sugar or carbocycle [20][21][22][23][24][25] followed by glycosylation to incorporate the purine or pyrimidine nucleobase. This approach leads to the formation of unwanted regioisomers that are difficult to separate.…”

Carbocyclic Analogues of Nucleosides from bis-(Hydroxymethyl)-cyclopentane: Synthesis, Antiviral and Cytostatic Activities of Adenosine, Inosine and Uridine Analogues

“…7,[9][10][11] However, reports of significant antiviral activity by nucleoside analogues with more than one hydroxymethyl group on the "sugar" ring (whether furan 12,13) or cyclobutane 14,15) ) soon led to investigation of a number of bis(hydroxymethyl)cyclopentane derivatives. [16][17][18] It was found that although (3S,4S)and rac-bis(hydroxymethyl)cyclopentyl adenine 3 are inactive against HIV-1, 16,17) (3S,4S)-3 is active against type 1 herpes simplex virus (HSV-1), with an IC 50 of less than 0.0001 mg/ml. 19) In this work we extended the search for bis(hydroxymethyl)cyclopentanes with antiviral and antitumour activities by preparing and screening seven that were chosen with a view to analysing the influence of various structural parameters on their biological activity.…”