(.+-.)-Carbocyclic 5'-nor-2'-deoxyguanosine and related purine derivatives: synthesis and antiviral properties

Journal of Medicinal Chemistry
1992.0

Abstract

Beginning with 3-cyclopenten-1-ylamine hydrochloride, the 5'-nor derivatives of carbocyclic 2'-deoxyguanosine (2), 2'-deoxyadenosine (3), and 2,6-diaminopurine 2'-deoxyribofuranoside (4) have been prepared. These compounds were evaluated for antiviral potential versus herpes simplex virus, varicella-zoster virus, cytomegalovirus, vaccinia virus, vesicular stomatitis virus, and human immunodeficiency virus and found to lack activity. Also, compounds 2-4 were virtually nontoxic toward the host (human diploid fibroblast ESM and HEL) cells. These biological properties may be due to the inability of 2-4 to be phosphorylated to the requisite nucleotide level that is likely to be necessary for biological activity by correlation to carbocyclic 2'-deoxyguanosine (1), which possesses significant antiviral properties as a result of conversion to its 5'-triphosphate derivative.

Knowledge Graph

Similar Paper

(.+-.)-Carbocyclic 5'-nor-2'-deoxyguanosine and related purine derivatives: synthesis and antiviral properties
Journal of Medicinal Chemistry 1992.0
Synthesis and antiviral evaluation of carbocyclic analogs of 2-amino-6-substituted-purine 3'-deoxyribofuranosides
Journal of Medicinal Chemistry 1987.0
Synthesis and antiviral activity of carbocyclic analogs of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines
Journal of Medicinal Chemistry 1984.0
Synthesis and biological evaluation of carbocyclic analogs of lyxofuranosides of 2-amino-6-substituted purines and 2-amino-6-substituted-8-azapurines
Journal of Medicinal Chemistry 1990.0
Synthesis and antiviral activity of carbocyclic analogs of xylofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines
Journal of Medicinal Chemistry 1987.0
Acyclic analogs of 2'-deoxynucleosides related to 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine as potential antiviral agents
Journal of Medicinal Chemistry 1985.0
Synthesis and antiviral evaluation of cyclopentyl nucleoside phosphonates
European Journal of Medicinal Chemistry 2018.0
Synthesis and antiviral evaluation of carbocyclic analogs of ribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines
Journal of Medicinal Chemistry 1984.0
Stereospecific synthesis and antiviral properties of different enantiomerically pure carbocyclic 2'-deoxyribonucleoside analogs derived from common chiral pools: (+)-(1R,5S)- and (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one
Journal of Medicinal Chemistry 1990.0
The synthesis and antiviral properties of (.+-.)-5'-noraristeromycin and related purine carbocyclic nucleosides. A new lead for anti-human cytomegalovirus agent design
Journal of Medicinal Chemistry 1992.0