Studies on the synthesis and biological activities of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines.
A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by 1H NMR.
Yu
H W
HW
School of Pharmaceutical Sciences, Beijing Medical University, People's Republic of China.
Zhang
L R
LR
Zhou
J C
JC
Ma
L T
LT
Zhang
L H
LH
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D002522:Chlorocebus aethiops; D018922:HL-60 Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009705:Nucleosides / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D011687:Purines / Q000737:chemistry* / Q000494:pharmacology; D011743:Pyrimidines / Q000737:chemistry* / Q000494:pharmacology; D018139:Simplexvirus / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship; D014709:Vero Cells
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D009705:Nucleosides; D011687:Purines; D011743:Pyrimidines