TY - JOUR
T1 - Synthesis and Antiviral Activity of Carbocyclic Analogues of Xylofuranosides of 2-Amino-6-substituted-purines and 2-Amino-6-substituted-8-azapurines
AU - Vince, Robert
AU - Turakhia, Rajesh H.
AU - Shannon, William M.
AU - Arnett, Gussie
PY - 1987/11/1
Y1 - 1987/11/1
N2 - (±Mla,2/5,3a,5a)-3-[(2,5-Diamino-6-chloro-4-pyrimidinyl)amino]-5-(hydroxymethyl)-l,2-cyclopentanediol (7) was synthesized from 2-amino-4,6-dichloropyrimidine and the carbocyclic xylofuranosylamine (±)-(la,2ft3a,5a)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol (2) by subsequent preparation of the 5-[(4-chlorophenyl)azo] derivative of the resulting pyrimidine and reduction of the azo moiety with zinc and acetic acid. The carbocyclic analogue of 2-amino-4-chloropurine xylofuranoside (8) and the corresponding 8-azapurine 11 were prepared from 7. The carbocyclic analogues xylofuranosylguanine (9), xylofuranosyl-2,6-diaminopurine (10), xylofuranosyl-8-azaguanine (13), and xylofuranosyl-8-aza-2,6-diaminopurine (14) were prepared from 8 and 11. Compounds 9 and 13 were active against herpes simplex virus (types 1 and 2), with 9 being the more potent against both viruses. Analogue 9 also exhibited potent activity against human cytomegalovirus and varicella-zoster virus.
AB - (±Mla,2/5,3a,5a)-3-[(2,5-Diamino-6-chloro-4-pyrimidinyl)amino]-5-(hydroxymethyl)-l,2-cyclopentanediol (7) was synthesized from 2-amino-4,6-dichloropyrimidine and the carbocyclic xylofuranosylamine (±)-(la,2ft3a,5a)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol (2) by subsequent preparation of the 5-[(4-chlorophenyl)azo] derivative of the resulting pyrimidine and reduction of the azo moiety with zinc and acetic acid. The carbocyclic analogue of 2-amino-4-chloropurine xylofuranoside (8) and the corresponding 8-azapurine 11 were prepared from 7. The carbocyclic analogues xylofuranosylguanine (9), xylofuranosyl-2,6-diaminopurine (10), xylofuranosyl-8-azaguanine (13), and xylofuranosyl-8-aza-2,6-diaminopurine (14) were prepared from 8 and 11. Compounds 9 and 13 were active against herpes simplex virus (types 1 and 2), with 9 being the more potent against both viruses. Analogue 9 also exhibited potent activity against human cytomegalovirus and varicella-zoster virus.
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U2 - 10.1021/jm00394a017
DO - 10.1021/jm00394a017
M3 - Article
C2 - 2822928
AN - SCOPUS:0023580039
SN - 0022-2623
VL - 30
SP - 2026
EP - 2030
JO - Journal of medicinal chemistry
JF - Journal of medicinal chemistry
IS - 11
ER -