104715-61-9

Usage

InChI:InChI=1/C9H11N5O2/c10-9-12-7-6(8(16)13-9)11-5-14(7)3-1-2-4-15/h1-2,5,15H,3-4H2,(H3,10,12,13,16)/b2-1+

Upstream product

• 104715-60-8 N²-acetyl-9-<(E)-4-hydroxybut-2-enyl>guanine 
• 116664-15-4 2-amino-9-<(E)-4-(benzoyloxy)-2-buten-1-yl>-6-chloropurine 
• 99776-30-4 N⁹-(4-Hydroxy-2-butyn-1-yl)guanine 
• 19962-37-9 N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide 
• 104715-58-4 N²-acetyl-9-<(E)-4-chlorobut-2-enyl>guanine 
• 10310-21-1 2-Amino-6-chloropurin 
• 105729-31-5 2-amino-6-chloro-9-(trans-4-chloro-2-buten-1-yl)purine 

Relevant academic research and scientific papers

Novel open-chain nucleotides imitating 2',3'-dideoxy-2',3'- didehydronucleotides: Synthesis and substrate properties toward DNA polymerases

A new series of acyclic nucleotide diphosphates was synthesized and evaluated as potential inbibitors of HIV reverse transcriptases.

GUANINE DERIVATIVE

Antivirally active compounds of the formula STR1 wherein A is STR2 wherein m is 1 or 2, n is 1 or 2, whereby m is 1 when n is 2 and m is 2 when n is 1, R a ' is (CH 2) p OH, NHCONH 2 or COR a ", R a " is hydrogen, hydroxy or amino, p is 1 to 4, R b ' and R b " are independently selected from hydrogen or (CH 2) p OH, with the proviso that at least one of R b ' or R b " is hydrogen; or R b ' and R b " together constitute an additional carbon-carbon bond to form an alkyne; or a physiologically acceptable salt, geometric or optical isomer thereof; pharmaceutical preparations containing the compounds and methods for treatment of virus infections.

Synthesis and antiherpetic activity of (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds

A series of analogues of acyclovir and ganciclovir were prepared in which conformational constrainst were imposed by incorporation of a cyclopropane ring or unsaturation into the side chain. In addition, several related base-modified compounds were synthesized. These acyclonucleosides were evaluated for enzymatic phosphorylation and DNA polymerase inhibition in a staggered assay and for inhibitory activity against herpes simplex virus types 1 and 2 in vitro. Certain of the guanine or 8-azaguanine derivatives were good substrates for the viral thymidine kinase and were further converted to triphosphate, but none was a potent inhibitor of the viral DNA polymerase. Nevertheless, one member of this group, (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine (3a), displayed significant antiherpetic activity in vitro, superior to that of the corresponding cis olefin 4a. Another group, typified by (±)-9-[[(E)-2-(hydroxymethyl)cyclopropyl]methyl]adenine (17b), possessed modest antiviral activity despite an apparent inability to be enzymatically phosphorylated. The relationship of side-chain conformation and flexibility to biological activity in this series is discussed.

Synthesis and Biological Properties of 9-(trans-4-Hydroxy-2-buten-1-yl)adenine and Guanine: Open-Chain Analogues of Neoplanocin A

Alkylation of adenine (5a) or 2-amino-6-chloropurine (5b) with excess trans-1,4-dichloro-2-butene (4), effected by K2CO3 in dimethyl sulfoxide or tetra-n-butylammonium fluoride in tetrahydrofuran, led 90-95percent regioselectivity to 9-alkylpurines 6a and 6b.The title compounds 2a and 2b were obtained by refluxing intermediates 6a and 6b in 0.1 M NaOH or HCl.Adenine derivative 2a is a substrate for adenosine deaminase whereas both 2a and 2b exhibit 50percent inhibition of growth of murine leukemia L 1210 cell culture at 1 mM concentration.