Phosphonate analogs of carbocyclic nucleotides.
Cyclopentadiene was converted in six steps to the key intermediate (+/-)-(1 alpha,2 beta,4 alpha)-4-amino-2-(benzyloxy)cyclopentanol (10), which in turn was converted to the carbocyclic nucleoside analogs 14 and 19 by standard procedures developed in these laboratories. Compounds 14 and 19 were then further converted to the target phosphonates 1b and 2b by modification of literature procedures. The phosphonate 1b was 40-fold more cytotoxic to HEp-2 cells than its parent, CDG, presumably after conversion to the diphosphoryl phosphonate.
Elliott
R D
RD
Southern Research Institute, Birmingham, Alabama 35255-5305.
Rener
G A
GA
Riordan
J M
JM
Secrist
J A
JA
Bennett
L L
LL
Parker
W B
WB
Montgomery
J A
JA
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002294:Carcinoma, Squamous Cell / Q000188:drug therapy; D006801:Humans; D007939:Leukemia L1210 / Q000188:drug therapy; D051379:Mice; D009712:Nucleotides, Cyclic / Q000138:chemical synthesis* / Q000494:pharmacology; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000494:pharmacology; D013552:Swine; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000970:Antineoplastic Agents; D009712:Nucleotides, Cyclic; D063065:Organophosphonates