144985-86-4

Upstream product

• 98-88-4 benzoyl chloride 
• 144985-85-3 (1R,2R)-1-benzyloxymethyl-2-hydroxymethylcyclopropane-1-methanol 
• 205043-74-9 (1S,7R)-1-benzyloxymethyl-4,4-dimethyl-3,5-dioxabicyclo[5.1.0]octane 
• 205043-71-6 (1R,7R)-4,4-Dimethyl-3,5-dioxa-bicyclo[5.1.0]octane-1-carboxylic acid ethyl ester 
• 144985-81-9 ethyl (1R,2R)-1,2-bis(hydroxymethyl)-1-cyclopropanecarboxylate 
• 205043-72-7 (1S,7R)-4,4-dimethyl-3,5-dioxabicyclo[5,1,0]oct-1-yl methanol 
• 145032-58-2 ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 
• 105-53-3 diethyl malonate 
• 100-39-0 benzyl bromide 

Downstream Products

• 145032-59-3 [(1S,2R)-2-[(benzoyloxy)methyl]-1-(hydroxymethyl)cyclopropyl]methyl benzoate 

Relevant academic research and scientific papers

Synthesis and antiviral activity of novel acyclic nucleosides: Discovery of a cyclopropyl nucleoside with potent inhibitory activity against herpesviruses

A series of acyclic nucleosides with two hydroxymethyl groups mimicking the 3'- and 5'-hydroxyl groups of the 2'-deoxyribose moiety were prepared and evaluated for their antiherpetic activity. Among those, 9-[[cis-1,2'- bis(hydroxymethyl)cycloprop-1'-yl]methyl]guanine (3) showed extremely potent antiviral activity against herpes simplex virus type-1 (HSV-1) with good selectivity. Both enantiomers of 3 were synthesized starting from chiral epichlorohydrins, and only one of the enantiomers with 1'S,2'R-configuration (3a) exhibited strong antiherpetic activity (IC50 of 0.020 μg/mL against HSV-1 Tomioka vs 0.81 μg/mL for acyclovir). Enantiomer 3a was also more inhibitory than acyclovir against varicella-zoster virus (VZV) but ineffective against human immunodeficiency virus (HIV). Compound 3a is phosphorylated by HSV-1 thymidine kinase (TK) very efficiently. The relationship between conformation and antiherpetic activity in this series of compounds is discussed.