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Carbocyclic analogs of thymine nucleosides and related 1‐substituted thymines
Author(s) -
Shealy Y. Fulmer,
O'Dell C. Allen,
Thorpe Martha C.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180231
Subject(s) - thymine , chemistry , thymidine , stereochemistry , biochemistry , dna
The carbocyclic analogs of thymidine (IXf), 1‐β‐ribofuranosylthymine (IXg), and 1‐β‐3′‐deoxyribofuranosyl‐thymine (IXe) were synthesized by incorporating modifications into the Shaw method of synthesizing 2,4‐(1 H ,3 H )pyrimidinediones via acryloylureas. Simpler analogs of thymine nucleosides were also prepared by this method. The carbocyclic analog of thymidine displayed modest activity against Leukemia L1210 in vivo. It differs from a compound prepared previously by a Prins reaction.