96480-03-4

Upstream product

• 96429-74-2 (S)-9-<<2,3-bis(benzyloxy)-1-propoxy>methyl>guanine 
• 34798-95-3 2-amino-N,N,N-trimethyl-9H-purine-6-ylammonium chloride 
• 98095-00-2 methyl 2,3,4-tri-O-benzyl-6-O-(2-amino-6-benzyloxypurin-9-ylmethyl)-α-D-glucopyranoside 
• 19916-73-5 2-Amino-6-benzyloxypurine 
• 18602-85-2 2,6,9-tris(trimethylsilyl)guanine 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 98095-03-5 (2S,1'S)-2-O-(2'-hydroxy-1'-methoxyethyl)-1-O-(guanin-9-ylmethyl)glycerol 

Relevant academic research and scientific papers

Guanine derivatives

(S)-9-(2,3-dihydroxy-1-propoxymethyl)guanine has potent antiherpetic activity which is superior to the corresponding racemic mixture or the (R)-enantiomer and also is much more potent than 9-(2-hydroxyethoxymethyl)guanine. Acyl derivatives (prodrugs) of t

SYNTHESIS OF THE CHIRAL ACYCLONUCLEOSIDE ANTIHERPETIC AGENT (S)-9-(2,3-DIHYDROXY-1-PROPOXYMETHYL)GUANINE

A new synthesis of the potential antiviral agent, (S)-9-(2,3-dihydroxy-1-propoxymethyl)guanine is described, starting from the readily available methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside.The sequence utilizes the absolute configuration defined by carb

Synthesis and antiherpetic activity of (S)-, (R)- and (±)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine, linear isomers of 2'-nor-2'-deoxyguanosine

Racemic 9-[2,3-dihydroxy-1-propoxy)methyl]guanine [(±)-iNDG], a new analogue of acyclovir (ACV) and a structural analogue of 2'-nor-2'-deoxyguanosine (2'NDG), was synthesized and found to inhibit the replication of herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). Subsequently, its optical isomers, (R)- and (S)-iNDG, were prepared from chiral intermediates. The chloromethyl ethers of 1,2-di-O-benzyl-D- and -L-glycerol were made and reacted with tris(trimethylsilyl)guanine to give the 9-alkylated guanines, which were deprotected by catalytic hydrogenolysis. Against HSV-1 and HSV-2 in cell culture, (S)-iNDG was approximately 10- to 25-fold more active than the R enantiomer and had an ED50 comparable to those for ACV and 2'NDG. The inferior activity of (R)-iNDG paralleled the poor inhibition of viral DNA polymerase by its phosphorylation products. In mice infected intraperitoneally or orofacially with HSV-1 or intravaginally with HSV-2, (S)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine [(S)-iNDG] was less efficacious than 2'NDG but comparable to or more active than ACV.